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Volume 30, Issue 11
Displaying 1-50 of 62 articles from this issue
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HIROFUMI TAKEUCHI, MASAHIRO KIKUCHI, YOSHIHISA MIWA, JUTARO OKADA1982 Volume 30 Issue 11 Pages 3865-3871
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe kinetics of liquid (organic)-liquid (aqueous) two-phase reactions on an immobilized phase transfer catalyst (triphase catalysis) was in vestigated. The displacement reactions of anions (aq. phase) on benzyl bromide or benzyl chloride (org. phase) were carried out at 90°C using tri-n-butylphosphonium chloride bound to 1% cross-linked polystyrene resin as a catalyst. The system was not stirred and all catalyst particles existed at the liquid-liquid interface. The observed sequence of nucleophilic reactivity of anions (CN-∼I->Br-, Cl-) is similar to that in a protic solvent. The reaction of benzyl bromide with potassium chloride was studied kinetically in detail. Under the experimental conditions used. all the mass transfer resistances had no significant effect and the rate of reaction was directly proportional to the amount of catalyst. The reaction order with respect to benzyl bromide was 0.73. From a consideration of the effects of concentrations of both chloride and bromide anions and the reverse reaction, a rate equation was developed.View full abstractDownload PDF (670K) -
SABURO SHIMABAYASHI, TOSHITAKA AOYAMA, MASAYUKI NAKAGAKI1982 Volume 30 Issue 11 Pages 3872-3881
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe formation of mixed precipitates of calcium diphosphate (Ca2PPi) and calcium orthophosphate (hydroxyapatite, HAP, mainly) from alkaline solutions of CaCl2, K2HPO4, K4P2O7 and NH4OH was studied. The chemical composition of the precipitate determined by direct chemical analysis of the precipitate was different from that obtained by calculation from the filtrate composition after incubation (72 h, 37°C). It was concluded that, although diphosphate (PPi) is usually hydrolyzed only in acidic solution, PPi was hydrolyzed to orthophosphate (Pi) on the surface of the precipitate in alkaline solution during the incubation, followed by further precipitate formation (CaPi) with excess Ca2+ in the solution. The extent of hydrolysis of PPi depended on the amounts of Ca2+ added and precipitate formed. It was confirmed that PPi is hydrolyzed in an alkaline solution of K4P2O7 depending on the amount of synthesized HAP or Ca2PPi, but is not hydrolyzed in the absence of any solid. HAP seems to catalyze the hydrolysis reaction of PPi more effectively than Ca2PPi. When the amount of Ca2+ was less than that of total phosphate, another counter cation in the precipitate was K+. X-Ray powder diffractometry of the precipitates revealed diffraction peaks of HAP, but those of Ca2PPi were not found. The precipitates formed in solutions containing enough Ca2+ were crystalline HAP, although the initial solution did not contain Pi but just PPi. The significance of this hydrolysis is discussed in relation to the formation of biological hard tissues.View full abstractDownload PDF (1024K) -
MITSUTOMO TSUHAKO, SHIGERU OHASHI, HIROYUKI NARIAI, ITARU MOTOOKA1982 Volume 30 Issue 11 Pages 3882-3889
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of trimetaphosphate (P3m) with glycine in an aqueous solution was studied. 1) P3m reacted with glycine at pH 10 and above to form two unknown compounds, A and B. 2) The amounts of these compounds were strongly affected by reaction conditions, such as the mixing ratio of P3m and glycine and the pH, and the yields of compounds A and B were around 26 and 24%, respectively. 3) Compound A was proved to be an orthophosphate derivative of glycine (P1-derivative of glycine), aminoacetyl phosphate, [chemical formula], while compound B was found to be a P1-derivative of glycine, N-(carboxymethyl) phosphoramidate, [chemical formula]. 4) It was found that glycylglycine (dimer), glycylglycylglycine (trimer), and higher oligopeptides of glycine were formed in the reaction of P3m and glycine. Further, in the reaction at pH 10-14, tetra-(P4) and pentaphosphate (P5) were also formed besides compounds A and B, though in small quantities. 5) Short-chain phosphates, such as ortho-(P1), pyro-(P2) and triphosphate (P3), did not react with glycine at all. 6) The mechanism of the reaction of P3m with glycine is discussed.View full abstractDownload PDF (766K) -
SETSUO SAITO, HIROSHI OZAKI, HAR EY A. ITANO1982 Volume 30 Issue 11 Pages 3890-3896
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 9, 10-phenanthrenequinone (PTQ) with cyclohexylguanidine or isopropylguanidine in alkaline aqueous ethanol yielded 1H-phenanthro [9, 10-d] imidazol-2-amine (PIA) as the major product and N-cyclohexyl-PIA or N-isopropyl-PIA, respectively, as a minor product. The same reaction with phenylguanidine or tert-butylguanidine yielded only the corresponding N-substituted PIAs. The yield of N-isopropyl-PIA was increased seven-fold when NaBH4 was added to the reaction mixture of PTQ and isopropylguanidine. N-Substituted PIAs are fluorescent and can be separated from PIA by thin layer chromatography.View full abstractDownload PDF (730K) -
FUMIKO ABE, TATSUO YAMAUCHI1982 Volume 30 Issue 11 Pages 3897-3905
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAffinogenin C and affinogenins D-I-V, cardenolides free from the component sugar, were isolated from the caules and leaves of Anodendron affine DRUCE, and their structures were established on the basis of spectrometric and chemical evidence.View full abstractDownload PDF (948K) -
KATSUHIDE MATOBA, NORIO KARIBE, TAKAO YAMAZAKI1982 Volume 30 Issue 11 Pages 3906-3911
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe title compound, 2-methoxy-4, 4-dimethyl-2, 5-cyclohexadienone (V), was prepared from 2-methoxy-4, 4-dimethyl-2-cyclohexenone (VIa). A methanolic solution of V was irradiated with a 200 W mercury lamp at -3°C to give 2, 2-dimethoxy-6, 6-dimethylbicyclo [3. 1. 0] hexan-3-one (X) and 6, 6-dimethoxy-5, 5-dimethyl-2-cyclohexenone (XI) in yields of 36.5 and 7.8%, respectively. On the other hand, a methanolic solution of V was irradiated in the presence of a catalytic amount of sulfuric acid to give only 2-methoxy-4-(1-methoxy-1-methylethyl)-2-cyclopentenone (XIII) in 35.4% yield. The behavior of V and VIa in the presence of a catalytic amount of acid is also described.View full abstractDownload PDF (665K) -
JUNICHI KITAJIMA, TETSUYA KOMORI, TOSHIO KAWASAKI1982 Volume 30 Issue 11 Pages 3912-3921
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn addition to trans-communol and trans-communic acid (obtained in the form of the methyl ester), seven new diterpenoids were isolated as non basic constituents from fresh bulbs of Fritillaria thunbergii MIQ. (Liliaceae). Their structures were determined to be isopimaran-19-ol (3), isopimaran-19-oic acid [obtained in the form of the methyl ester (4)], ent-kauran-16β, 17-diol (5), ent-kauran-16α, 17-diol (6), ent-16β, 17-epoxy-kaurane (7), ent-16α-methoxy-kauran-17-ol (8), and ent-kaur-15-en-17-ol (9).View full abstractDownload PDF (894K) -
JUNICHI KITAJIMA, NAOKI NODA, YOSHITERU IDA, TETSUYA KOMORI, TOSHIO KA ...1982 Volume 30 Issue 11 Pages 3922-3931
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new diterpenoids, in addition to trans-communol (1), trans-communic acid [obtained in the form of the methyl ester (2)], isomimaran-19-ol (3), isopimaran-19-oic acid [obtained in the form of the methyl ester (4)], ent-kauran-16β, 17-diol (5), ent-kauran-16α, 17-diol (6) and ent-17-norkauran-16-one (7), were isolated as non basic constituents of the crude drug "Fritillariae Bulbus" prepared from the bulbs of Fritillaria thunbergii MIQ. by treatment with lime followed by bleaching in the sun. These three diterpenoids were determined to be ent-15β, 16-epoxy-kauran-17-ol (8), ent-16β-hydroxy-kauran-17-yl ent-kaur-15-en-17-oate (9) and ent-(16S)-atisan-13, 17-oxide (10).View full abstractDownload PDF (831K) -
MASAHIKO KIMURA, KOJI HAYASHI, HIROSHI NARITA, HIROSHI MITSUHASHI1982 Volume 30 Issue 11 Pages 3932-3941
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour 18-oxygenated pregnane-type steroids ; 18, 20-epoxypregn-5-en-3β-ol acetate (III), 18, 20-epoxy-isolineolon cyclic sulfite (VIII), 18, 20-epoxy-deacyl condurangogenin C (XVIII), and 18, 20-epoxy-20-epideacyl condurangogenin C (XXI) were synthesized, and their structures were established by chemical and spectral studies. A remarkable difference in 13C-nuclear magnetic resonance chemical shifts between 20R-and 20S-hydroxy-C/D-cis-pregnane-type steroids was found.View full abstractDownload PDF (943K) -
SHINICHI UESATO, KOJI KOBAYASHI, HIROYUKI INOUYE1982 Volume 30 Issue 11 Pages 3942-3950
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFor studies on the biosynthesis of iridoid glucosides, four labeled compounds, i.e., [10-3H]-iridotrial (4), [10-3H]-7, 8-dehydroiridodial (6), [10-3H]-7, 8-dehydroiridotrial (7) and [10-2H3]-iridodial (3), along with the known [10-3H]-iridodial glucoside (10) and [10-3H]-iridodial (3) were prepared from geniposide (11). Furthermore, [11-2H3]-7, 8-dehydroiridodial (6) was derived from mussaenoside (14).View full abstractDownload PDF (1075K) -
TOSHIAKI WAKABAYASHI, SHINRO TACHIBANA1982 Volume 30 Issue 11 Pages 3951-3958
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIt has been found that N-methylimidazole (MeIm) activates stable condensing reagents such as 2, 4, 6-triisopropylbenzenesulfonyl-4-nitroimidazolide (TPSNI) and mesitylenesulfonyl-4-nitroimidazolide (MSNI). Fully protected trinucleotides which could serve as key intermediates were synthesized by using MeIm and TPSNI or MSNI. These trinucleotides were utilized in the syntheses of the dodecamers, dCATCCACCCCAT and dAGCCATCTGCTT, which correspond to the specific tetrapeptides of cholecystokininpancreozymin and vasoactive intestinal peptide.View full abstractDownload PDF (792K) -
HIROKI TAKAHATA, AKIRA TOMIGUCHI, ATSUSHI HAGIWARA, TAKAO YAMAZAKI1982 Volume 30 Issue 11 Pages 3959-3964
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of ketene-S, N-acetals (1a-c) derived from lactams with dimethyl acetylenedicarboxylate (DMAD) gave the ring-expanded products (3a-c, respectively). On the other hand, similar treatment of N-acetyl ketene-S, N-acetals (5b, c) afforded the [2+2] adducts (6b, c, respectively). Next, the reaction of benzoketene-S, N-acetals (8a-c) with DMAD furnished the ringopened products (13a-c, respectively).View full abstractDownload PDF (685K) -
MASASHI TOMODA, NORIKO SHIMIZU1982 Volume 30 Issue 11 Pages 3965-3969
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA mucous polysaccharide, named Lycoris-R-glucomannan, was isolated from the bulbs of Lycoris radiata HERBERT. The final preparation was homogeneous as determined by ultracentrifugal analysis, glass-fiber electrophoresis, and gel chromatography. It was composed of D-mannose and D-glucose in the molar ratio of 12 : 1, and its molecular weight was estimated to be 468000. O-Acetyl groups were identified in the glucomannan and their content amounted to 15.5%. They were located at positions 2, 6 of some of the D-mannose units. Methylation, periodate oxidation, and partial acid hydrolysis studies showed that the glucomannan is mainly composed of β-1→4 linked aldohexopyranose residues, and that it contains about thirteen aldohexose units per three non-reducing groups on average. D-Mannose units occupy non-reducing terminal positions and branching points linked through both positions 3 and 6.View full abstractDownload PDF (637K) -
KOICHI YASUMURA, KENJI OKAMOTO, HARUAKI YAJIMA1982 Volume 30 Issue 11 Pages 3970-3976
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe docosapeptide H-Arg-Pro-Val-Lys-Val-Tyr-Thr-Asn-Gly-Val-Glu-Glu-Gln-Ser-Ser-Glu-Gly-Phe-Pro-Ser-Glu-Met-OH, corresponding to the amino acid sequence of salmon corticotropin-like intermediate lobe peptide (CLIP), was synthesized, with the use of 1 M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid as a deprotecting reagent.View full abstractDownload PDF (888K) -
HIKARU OKABE, YUMI MIYAHARA, TATSUO YAMAUCHI1982 Volume 30 Issue 11 Pages 3977-3986
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral non-bitter cucurbitacin glycosides were isolated together with two bitter cucurbitacin glycosides from the immature fruits of Momordica charantia L. (Cucurbitaceae), and four of the non-bitter glycosides, momordicosides G, F1, F2 and I, were characterized from chemical and spectral evidence as folows ; G, 3-O-β-D-allopyranoside of 5, 19-epoxy-25-methoxy-5β-cucurbita-6, 23-dien-3β-ol ; F1, 3-O-β-D-glucopyranoside of 5, 19-epoxy-25β-methoxy-5β-cucurbita-6, 23-dien-3β-ol ; F2, 3-O-β-D-allopyranoside of 5, 19-epoxy-5β-cucurbita-6, 23-diene-3β, 25-diol ; I, 3-O-β-D-glucopyranoside of 5, 19-epoxy-5β-cucurbita-6, 23-diene-3β, 25-diol.View full abstractDownload PDF (1107K) -
KATSUMI TABEI, ETSUKO KAWASHIMA, TOYOZO TAKADA, TETSUZO KATO1982 Volume 30 Issue 11 Pages 3987-3993
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of benzamide oxime derivatives (1) with ethyl γ-bromoacetoacetate in the presence of an acidic catalyst gave a mixture of geometrical isomers of 3-aryl-5-ethoxycarbonylmethylene-5, 6-dihydro-4H-1, 2, 4-oxadiazine derivatives (5) in 60-75% yields. On separation of the mixtures by HPLC, the (Z)-ester (5-I) was obtained as the main product (60-70% yields) together with the (E)-ester (5-II) (3-5% yields). The structures of these isomers were determined by analysis of the IR and NMR spectra. Methyl γ-bromoacetoacetate, p-methyl-γ-bromoacetoacetanilide and p-toluamide O-(γ-bromoacetoacetyl) oxime were also reacted with 1 to afford the corresponding 3-aryl-5-(substituted) methylene-5, 6-dihydro-4H-1, 2, 4-oxadiazine derivatives (8-I, 8-II, 9, and 10) in moderate yields.View full abstractDownload PDF (703K) -
MASAHITO OCHIAI, EIICHI FUJITA, MASAO ARIMOTO, HIDEO YAMAGUCHI1982 Volume 30 Issue 11 Pages 3994-3999
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA direct allylation of aromatic compounds using allylsilane, allylgermane, or allylstannane (1) and arylthallium bis (trifluoroacetate) has been developed. The actual transmetalation reagent for 1 in the reaction was proposed to be thallium (III) trifluoroacetate (2), which was produced together with diarylthallium trifluoroacetate by the disproportionation of arylthallium bis (trifluoroacetate).View full abstractDownload PDF (606K) -
KEI TAKEDA, MIKAKO SHINAGAWA, TORU KOIZUMI, EIICHI YOSHII1982 Volume 30 Issue 11 Pages 4000-4005
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThermal intramolecular Diels-Alder reaction of methyl (or ethyl) (2E, 8E, 10E)-12-methoxymethoxy-2-methyl-2, 8, 10-dodecatrienoate (4) was found to give a ca. 1 : 1 mixture of trans and cis octalins (10, 11) in a good combined yield. The stereochemistries of 10 and 11 were determined by comparisons of their 1H nuclear magnetic resonance spectra and by the observation that only 10 formed a γ-lactone (12) on acid treatment. Preparation of 4 from 6-(tetrahydropyran-2-yl) oxyhexan-1-ol (5) by seven step sequence of reactions is also described.View full abstractDownload PDF (655K) -
SHIGEO IWASAKI, MICHIO NAMIKOSHI, KEIZO SASAKI, KAZUTAKA FUKUSHIMA, SH ...1982 Volume 30 Issue 11 Pages 4006-4014
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of the antibiotics azalomycin F3a (1b) (C55H93N3O17) and azalomycin F5a (1c) (C57H97N3O17) were elucidated by comparison of their physicochemical properties with those of F4a (1a) (C56H95N3O17). Structural differences among these three compounds lie only in their guanidine moieties, which have no methyl group, one methyl group and two methyl groups in F3a, F4a and F5a, respectively.View full abstractDownload PDF (716K) -
KENICHI NUNAMI, MAMORU SUZUKI, NAOTO YONEDA1982 Volume 30 Issue 11 Pages 4015-4024
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious α-alkylated β, γ-unsaturated α-amino acids were synthesized by the deconjugative alkylation of methyl α-isocyanoalkylideneacetates followed by hydrolysis. In the mechanistic study, no marked differences in reactivity of the geometrical isomers of methyl 2-isocyano-3-phenyl-2-butenoate (E-and Z-11a) were observed. On the other hand, the double bound migration of unsymmetrical (R1≠R2) isocyano compounds (11c, d) proceeded regioselectively due both to the different acidities of the alkyl groups and to the stability of the carbanion formed on proton abstraction. Furthermore, direct synthesis of methyl α-isocyanocycloalkylideneacetates (4a, b, d) by the reaction of methyl isocyanoacetate with cyclic ketones was also investigated.View full abstractDownload PDF (882K) -
TADAMI FUJIWARA, TADAHIRO TAKEDA, YUKIO OGIHARA, MASAKI SHIMIZU, TAKEO ...1982 Volume 30 Issue 11 Pages 4025-4030
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWater-soluble polysaccharides, designated as GIa and GIb, were isolated from the bark of Melia azadirachta (Meliaceae) and their inhibiting effect on subcutaneously inoculated Sarcoma-180 was tested. GIa and GIb each gave a single peak on ultracentrifugation and gel filtration. Methylation, periodate oxidation and 13C-NMR spectroscopic studies suggested that GIa is composed of the following repeating unit ; α-D-Glc 1→4α-D-Glc 1→4α-D-Glc 1→4α-D-Glc 1→4α-D-Glc 6←1α-L-Araf. GIb is a branched arabinofucoglucan, containing a main chain of (1→4)-linked α-D-glucopyranosyl units substituted in the 6 position with side chains of α-L-arabinofuranosyl units. 3-O-substituted fucopyranose is attached to the α-(1→4) glucose units at the 4 position in the main chain.View full abstractDownload PDF (648K) -
KEISHI FUNAKI, KEI TAKEDA, EIICHI YOSHII1982 Volume 30 Issue 11 Pages 4031-4036
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMethyl α-and β-DL-2, 3, 4, 6-tetradeoxy-4-(methoxycarbonylamino)-3-C-methyl-3-nitro-xylo-hexopyranosides (13a, b) were synthesized from methyl α-and β-DL-2, 3, 4, 6-tetradeoxy-hex-3-enopyranosides (2). The key step in the syntheses involved regio-and stereospecific addition of jodine isocyanate to the starting unsaturated sugar.View full abstractDownload PDF (736K) -
TAKESHI IMANISHI, HIROAKI SHIN, MIYOJI HANAOKA, TAKEFUMI MOMOSE, ICHIR ...1982 Volume 30 Issue 11 Pages 4037-4045
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBase-catalyzed reaction of N-substituted 1, 6-dihydro-3 (2H)-pyridinones (1 and 2) with some 1, 3-dicarbonyl compounds (8a-e) resulted in exclusive formation of the 2-azabicyclo [2. 2. 2] octan-7-ones (5 and 6), while a similar treatment of 1 with dimethyl acetonedicarboxylate (8f) gave the 3-azabicyclo [3. 3. 1] nonan-7-one (10f) as a sole product. On deethoxycarbonylation under acidic conditions, the azabicyclooctanecarboxylates (5a, 5c, 6a, and 6c) afforded the 3-azabicyclo [3. 3. 1] nonanes (13 and 16) and/or the 2-azabicyclo [2. 2. 2] octanes (14, 15, 17, and 18). On the other hand, ketalization of a mixture of 17 and 18 with ethylene glycol provided the diketal (23), which was derived into the monoketone (24) upon treatment with 98% formic acid. Haloform reaction of 24 followed by esterification yielded the ester (26), which was transformed into the aldehyde (28) by sodium borohydride reduction and subsequent PCC oxidation. An acidic hydrolysis of 28 directly furnished the desired 2-azabicyclo [2. 2. 2] octanone derivative (7), a possible synthon for the Iboga alkaloids.View full abstractDownload PDF (874K) -
NORIO AIMI, TOSHIAKI SHITO, KAYOKO FUKUSHIMA, YUMIKO ITAI, CHIFUMI AOY ...1982 Volume 30 Issue 11 Pages 4046-4051
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new glycoindole alkaloid, rhynchophine, was isolated from the leaves of Uncaria rhynchophylla MIQ. and its structure was elucidated as 6'-feruloyl vincoside lactam (IV). A partial synthesis was achieved by the use of vincoside lactam as the starting material. Five known compounds were also newly isolated from the same plant, namely, vallesiachotamine, vincoside lactam, strictosamide, hyperin and trifolin.View full abstractDownload PDF (691K) -
TAKESHI IMANISHI, NORIYUKI YAGI, HIROAKI SHIN, MIYOJI HANAOKA1982 Volume 30 Issue 11 Pages 4052-4059
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOn treatment with ethyl vinyl ether containing mercuric acetate, the allylic alcohol (5) afforded the aldehyde (7), which was acetalized to 8. Hydroboration-oxidation of 8 was followed by pyridinium chlorochromate (PCC) oxidation to yield two isomeric ketones (11 and 12), of which the former was subjected to acidic hydrolysis to afford the 2-azabicyclo [2. 2. 2] octanone (3b) in excellent yield. On the other hand, the diketal (22) derived from 11 also gave the N-benzyloxycarbonyl analogue (3c) on acidic treatment. Ketalization of 3c and subsequent oxidation provided the ketone (27), which was transformed into the amide (29) via the amine (28). Cyclization of 29 furnished the pentacyclic product (30), which has already been converted into (±)-catharanthine (4) and (±)-velbanamine (31).View full abstractDownload PDF (847K) -
YOSHIO OKADA, YUKO TSUDA, AKIO HIRATA, YOKO NAGAMATSU, UTAKO OKAMOTO1982 Volume 30 Issue 11 Pages 4060-4068
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious peptide anilides were synthesized by a conventional method with the object of obtaining specific substrates for human spleen fibrinolytic proteinase (SFP) and human leukocyte elastase (LE) in order to compare the substrate specificity of SFP with that of LE. It was found that the P1 Val compound among succinyl tripeptide p-nitroanilides (Suc-Tyr-Leu-X-pNA) exhibited the highest kcat/Km values for hydrolysis by SFP and LE, however, the tetrapeptide Suc-Ala-Tyr-Leu-Val-pNA [kcat/Km values (M-1S-1) for hydrolysis by SFP and LE : 84000 and 48000, respectively] was the preferred chromogenic substrate for SFP and LE because of its high solubility in the buffer and its moderate kcat/Km values. The substrate specificity of SFP was found to be similar to that of LE.View full abstractDownload PDF (1016K) -
YASUMITSU TAMURA, CHISATO MUKAI, MASAZUMI IKEDA1982 Volume 30 Issue 11 Pages 4069-4074
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe N-tosylsulfilimines and (bismethoxycarbonyl) methylides of 1, 4-dimethylthioxanthene and its 9-alkyl derivatives were synthesized, and their stereochemistry was assigned on the basis of nuclear magnetic resonance spectral comparison with the corresponding 2, 4-dimethylthioxanthene derivatives. Treatment of 1, 4-dimethylthioxanthene N-tosylsulfilimine and 1, 4-dimethylthioxanthenium (bismethoxycarbonyl) methylide with base gave the rearranged products, 9-tosylamino-and 9-(bismethoxycarbonyl) methyl-1, 4-dimethylthioxanthenes, respectively, but the 9-alkyl derivatives did not undergo this rearrangement.View full abstractDownload PDF (637K) -
KAZUTAKE SHIMADA, TOMOKO KYUNO, TOSHIO NAMBARA, ITSUO UCHIDA1982 Volume 30 Issue 11 Pages 4075-4081
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSix cardiac glycosides having a methylenedioxy group in the sugar moiety, elaeodendroside A, D, E, H, I and J, were isolated from seeds of Elaeodendron glaucum PERS. Their structures were elucidated on the basis of chemical correlation with elaeodendroside A, which was characterized by X-ray analysis. A new cradiac steroid named elaeodendrogenin was also isolated from the same plant materials and its structure was established by direct comparison with a synthetic sample obtained from digitoxigenin. The cardiac activities of these compounds were tested with Straub's preparation.View full abstractDownload PDF (893K) -
TAKAO KONOSHIMA, TOKUNOSUKE SAWADA1982 Volume 30 Issue 11 Pages 4082-4087
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree triterpenoid saponins named gleditsia saponins D2 (VII), G (IV) and I (VIII) were isolated from the legume of Gleditsia japonica cv.'Saponifera.' They were characterized as echinocystic acid 3, 28-O-bisglycosides acylated with two monoterpene carboxylic acids IX and X. The locations of these monoterpenes were established by 13C nuclear magnetic resonance spectroscopy.View full abstractDownload PDF (636K) -
IKUNORI SAKAMOTO, TAKASHI TANAKA, OSAMU TANAKA, TSUYOSHI TOMIMORI1982 Volume 30 Issue 11 Pages 4088-4091
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new xanthone glucoside named isoswertianolin (2) was isolated from Swertia japonica and its structure was elucidated to be 5-O-β-glucopyranoside of bellidifolin by 1H and 13C nuclear magnetic resonance (NMR) spectroscopy. In connection with this study, the structure of swertianolin (1), a constituent of this plant, was reinvestigated by NMR spectroscopy, leading to the revision of its structure (the location of its glucosyl linkage) from 1-O-β-glucopyranoside of bellidifolin (3) to 8-O-β-glucopyranoside of 3. It follows that 1 is identical with the glucoside isolated from Gentiana campestris by Kaldas et al. in 1974. Analogously, the structure of norswertianolin (6), previously isolated from Swertia randaiensis HAYATA, was also revised, being formulated as 8-O-β-glucopyranoside of desmethylbellidifolin (7).View full abstractDownload PDF (467K) -
TAKASHI FUJIKURA, KUNIHIRO NIIGATA, SHINICHI HASHIMOTO, KAZUO IMAI, TO ...1982 Volume 30 Issue 11 Pages 4092-4101
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew α-and β-adrenergic blockers, benzenesulfonamide derivatives (Ia-z), were prepared from acetylbenzenesulfonamides (II) by two methods. These compounds were tested for α-and β-blocking activities and their structure-activity relationships are discussed. All the target compounds have two asymmetric centers and therefore consist of two diastereomers. 5-[1-Hydroxy-2-[3-(2-methoxyphenyl)-1-methylpropylamino]ethyl]-2-methylbenzenesulfonamide (Ir) and 5-[1-hydroxy-2-[2-2-(2-methoxyphenoxy)-1-methylethylamino] ethyl]-2-methylbenzenesulfonamide (Iu) showed potent α-and β-blocking activities and they were each separated into two diastereomers (Ir-A and Ir-B, and Iu-A and Iu-B). It was found that one isomer had mainly β-blocking activity and the other isomer had mainly α-blocking activity. In addition, several compounds showing relatively strong α-and β-blocking activities were also examined for antihypertensive activity in conscious spontaneously hypertensive rats. Among the compounds tested, Ir and Iu were the most active, and they were more potent than labetalol. Compounds Ir and Iu may be of practical use as potent antihypertensive agents.View full abstractDownload PDF (944K) -
MAKSUT COSKUN, AKIYO SAKUSHIMA, SANSEI NISHIBE, SUEO HISADA1982 Volume 30 Issue 11 Pages 4102-4106
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe phloroglucinol derivatives of Dryopteris abbreviata (DC.) NEWMAN from Turkey, a member of the European D. filix-mas complex, were investigated. A known compound, flavaspidic acid PB (I), and three new compounds, designated as dimethylphlorobutyrophenone (II), abbreviatin PB (III) and trisabbreviatin BBB (IV), were isolated in addition to the already reported compounds, filixic acid, flavaspidic acid AB and abbreviatin BB (V). This is the first report of the occurrence of a series of phloroglucinol derivatives lacking the filicinic acid ring moiety, i.e., compounds II, III, IV and V, in European taxa of the D. filix-mas complex.View full abstractDownload PDF (536K) -
YOSHITATSU HAYASHI, SOHACHIRO MIYAKE, MOTOAKI KUWAYAMA, MASATOSHI HATT ...1982 Volume 30 Issue 11 Pages 4107-4113
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA high performance liquid chromatographic method using a fluorimetric detector for determination of the quantities of 6-amino-2-phenylamino-9-β-D-ribofuranosyl-9H-purine (CV-1808, 1) and its metabolite, 2-(4-hydroxyphenyl) aminoadenosine (2), in human serum and urine is presented. Compounds 1 and 2, after chromatographic extraction from urine or serum with a Sep-Pak C18 cartridge, are allowed to react with propionic anhydride in the presence of triethylamine and the quantities of the resulting propionyl derivatives of 1 and 2 (1-P and 2-P) are determined by high performance liquid chromatography on a μPorasil column. The detection limits of 1 and 2 are 5.0 and 10.0 ng/ml in urine and 1.0 and 2.0 ng/ml in serum, respectively. For a more sensitive determination of the amount of 1 in serum, a concentrated eluate of 1-P from the μPorasil column is rechromatographed on a minicolumn (10 cm×2 mm I.D.) packed with Lichrosorb SI-60 (5μm). With this method, a detection limit of 0.1 ng/ml for 1 in serum is obtained.View full abstractDownload PDF (648K) -
KIYOSHI ZAITSU, KENICHIRO NAKASHIMA, SHUZO AKIYAMA, YOSUKE OHKURA1982 Volume 30 Issue 11 Pages 4114-4119
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA rapid sandwich-type enzyme immunoassay of human choriogonadotropin in 20 μl of serum is described. Anti-human choriogonadotropin β subunitantibody (IgG fraction) was coated on an acrylonitrile-butadiene-styrene copolymer bead. The bead was incubated with choriogonadotropin in serum at 30°C for 2 (or 3) h, and again incubated at 30°C for 2 (or 3) h with antibody-labeled horseradish peroxidase prepared by Nakane and Kawaoi's method, to form a sandwich-type immunocomplex. The enzyme activity of the complex on the bead was measured by the use of a sensitive fluorogenic substrate, 3-(p-hydroxyphenyl) propionic acid. The method permits one-day assay of 0.0125-64 ng (2.75-14080 mIU) of the hormone.View full abstractDownload PDF (585K) -
AKIRA TAKADATE, TSUTOMU TAHARA, HIROYUKI FUJINO, SHUJIRO GOYA1982 Volume 30 Issue 11 Pages 4120-4125
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS4-Diazomethyl-7-methoxycoumarin (DMC) was synthesized as a new fluorescent labeling reagent for hydroxyl and carboxyl compounds for use in high-performance liquid chromatography. Treatment of 4-formyl-7-methoxycoumarin with p-toluenesulfonohydrazide gave the tosylhydrazone in 78% yield, and this was derived to DMC in 78% yield by treatment with 0.2N NaOH. DMC was practically nonfluorescent in solution and possessed excellent storage properties. DMC reacted with alcohols in dichloromethane at room temperature in the presence of HBF4 as a catalyst to give the corresponding fluorescent coumarin ethers and also reacted with carboxylic acids in acetonitrile on heating to give the esters. DMC derivatives of cholestanol and cholesterol were satisfactorily separated by high-performance liquid chromatography. The present studies indicate that DMC is a useful fluorescent reagent for the labeling of alcohols and carboxylic acids.View full abstractDownload PDF (572K) -
KAZUNOBU MIURA, TATSUYOSHI IWANO, SHIGEKI TSUDA, TOHRU UEDA, FUMIO HAR ...1982 Volume 30 Issue 11 Pages 4126-4133
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe conversion of cytosine residue of transfer ribonucleic acid (tRNA) to 4-thiouracil residues was carried out with a hydrogen sulfide-pyridine-water system. In the case of tRNAVal from mouse cells, the cytosine moieties located in unpaired and looped-out regions of the molecule, such as the anticodon and CCA-end regions, were converted. This result shows that the secondary and tertiary structures of tRNA are maintained even in medium containing liquid hydrogen sulfide and pyridine, and hence, this system should be suitable for studies of the higher-order structure of nucleic acids.View full abstractDownload PDF (852K) -
TOSHIHIRO FUJII, YOSHIYUKI KONDO, MICHIYO KUMASAKA, AKIRA HACHIMORI, K ...1982 Volume 30 Issue 11 Pages 4134-4139
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTubulin subjected to heat, urea, or guanidine hydrochloride treatment differed in some respects from native tubulin, which inhibits actomyosin Mg-adenosine triphosphatase (ATPase) activity and the corresponding turbidity change. Whereas native tubulin inhibited 65% of actomyosin Mg-ATPase activity, tubulin heated at 65-70°C for 3 min reduced the ATPase activity to 8% of the original level. The effective inhibition by tubulin was gradually diminished when tubulin was treated above 75°C. Since such treated tubulin had little effect on myosin Mg-ATPase activity, it seems to inhibit the actin activation through its binding to myosin. The changes of turbidity inhibition of actomyosin by tubulins were similar to those in ATPase inhibition. Heat treatment converted the conformation of tubulin from α-helix to β-structure, and heat-treated tubulin was easily degraded by trypsin. Tubulin denatured with urea or guanidine hydrochloride showed less ATPase inhibition than heat-treated tubulin.View full abstractDownload PDF (688K) -
HAJIME INOUE, EIJI USAMI, YOSHIYUKI SEYAMA, SABURO YAMASHITA1982 Volume 30 Issue 11 Pages 4140-4143
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHuman lung arylsulfatase activity was determined by a fluorometric microanalytical method with 4-methylumbelliferyl sulfate as the substrate. By the use of a suitable deproteinizing agent after the enzymatic reaction, arylsulfatase activity in whole blood could be determined at the picomole level ; without deproteinization, the blank value was higher because of turbidity due to protein. The present method is approx. 2000 times more sensitive than the conventionally used spectrophotometric method of arylsulfatase activity determination. It was found in the present study that the optimum pH's of AS-A and AS-B were different when p-nitrocatechol sulfate was used as the substrate : optimum pH for AS-A=4.2 ; that for AS-B=5.5.View full abstractDownload PDF (496K) -
HIROSHI UEKI, MIKIKO ARAKI, AKIRA NAGAYOSHI, TAKAYUKI FUNAKOSHI, SHOZO ...1982 Volume 30 Issue 11 Pages 4144-4152
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn acid-stable N-succinyl-L-trialanine p-nitroanilide-hydrolyzing protease was purified from Pronase E with a protein yield of 6% by affinity chromatography on arginine peptides-Sepharose or soybean trypsin inhibitor-Sepharose. The enzyme showed a potent increasing effect on the glycogen content in an isolated mouse diaphragm. It was homogeneous both in disc and sodium dodecyl sulfate-polyacrylamide gel electrophoresis, had an optimum pH of 8.5, and was stable in the pH range from 2 to 10, whereas its activity was lost at pH 12. Its molecular weight was estimated to be 20800. The sequence up to thirty-two residues from the N-terminus was determined with guanidine-treated and S-carboxymethylated enzymes. The N-and C-terminal residues were isoleucine and tyrosine, respectively. The results suggest that this enzyme is mainly responsible for the insulin-like activity of Pronase and that it is homologous with Protease B which was purified from Pronase B (L. Jurasek, M. R. Carpenter, L. B. Smille, A. Gertler, S. Levy, and L. H. Ericsson, Biochem. Biophys. Res. Commun., 61, 1095 (1974)), though some differences were found between the C-terminal regions of the two enzymes.View full abstractDownload PDF (963K) -
HIROSHI FUJIWARA, SUSUMU KAWASHIMA, YUTAKA YAMADA1982 Volume 30 Issue 11 Pages 4153-4158
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIt is well known that the degradation of ampicillin is accelerated by various kinds of carbohydrates in neutral and alkaline aqueous solutions. Thus, the kinetics of ampicillin degradation in the presence of carbohydrate and furfural were investigated to determine how the rate-accelerating effect of carbohydrate is inhibited by furfural. The rate accelerating effect of carbohydrates increased with increasing molecular weight of the carbohydrates. However, the accelerating effects of sucrose, glucose, maltose and dextran 40 were all inhibited by the addition of furfural at pH 7-9. This inhibition is due to the resistance of the Schiff base, which is formed between ampicillin and furfural, to the action of carbohydrate, presumably because of steric hindrance.View full abstractDownload PDF (588K) -
KENICHI SASAKI, SHINOBU FURUSAWA, GIICHI TAKAYANAGI1982 Volume 30 Issue 11 Pages 4159-4163
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of doxapram, a respiratory stimulant, on the formation of lipid peroxide was investigated in mice. A significant increase of lipid peroxide was observed in the liver after injection of doxapram (100 mg/kg, i.p.) and the level of lipid peroxide was about 5-fold greater than that of control mice at 4 h after injection. However, no increase of lipid peroxide was observed in the brain, heart, lung, spleen or kidney of mice treated with doxapram. On the other hand, doxapram initially increased the activity of xanthine oxidase but significantly reduced it from about 4 h after injection, and also reduced the activities of superoxide dismutase and glutathione peroxidase in the liver. The level of α-tocopherol decreased slightly in the liver after administration of doxapram. This enhancement of lipid peroxidation in the liver in doxapram-treated mice suggests that an increase of superoxide anion and an inhibition of free radical scavenging reactions in vivo may be produced by the drug.View full abstractDownload PDF (547K) -
TAMIO MAITANI, KAZUO T. SUZUKI1982 Volume 30 Issue 11 Pages 4164-4169
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMale ICR mice were injected intraperitoneally with various heavy metals (chromium, manganese, iron, cobalt, nickel, zinc, selenium, indium and lead) at an equimolar dose (150μmol/kg body weight) to compare the abilities of the metals to induce zinc-thionein (Zn-Th) in the liver. Metallothionein (MT) level was determined for cadmium-replaced liver supernatant fractions by high performance liquid chromatography-atomic absorption spectrophotometry. All the metals induced Zn-Th to some degree ; the strongest inducers were zinc and indium, and the weakest was iron. Selenium, previously reported to be unable to induce MT, also gave a fairly high level of Zn-Th at the lower dose of 30 μmol/kg (it was lethally toxic at the standard dose). Changes in the concentrations of some essential metals in the liver were also determined by the use of an inductively coupled plasma-atomic emission spectrometer in order to correlate the extents of MT induction with the changes of essential metal levels.View full abstractDownload PDF (648K) -
KEIZO MATSUO, MASAO OKUMURA, KUNIYOSHI TANAKA1982 Volume 30 Issue 11 Pages 4170-4174
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMimocin, which is an isoquinolinequinone antibiotic, was synthesized starting from 2, 3, 6-trimethoxytoluene.View full abstractDownload PDF (639K) -
CHISAKO YAMAGAMI, CHIHOKO SONODA, NARAO TAKAO, MITSUYO TANAKA, JUN YAM ...1982 Volume 30 Issue 11 Pages 4175-4180
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of m-and p-substituted benzyl N, N-dimethylcarbamates was prepared then evaluated for anticonvulsant activity in mice by means of the maximal electroshock seizure test. The ED50 value correlated well with the hydrophobic (log P, 1-octanol-H2O partition coefficient), electronic (σ°) and hydrogen bonding (HB) characters of the tested compounds on regression analyses. The relative activity depended parabolically on log P ; the optimum value of hydrophobic character (log P0) was 1.82. This agrees well with values found empirically for central nervous system depressants (log P0≃2). Electron-donating substituents enhanced the activity, an indication of interaction between the carbamoyl moiety and an acidic group on the receptor site. Hydrogen bond-accepting ability of the substituent reduced anticonvulsant activity, while non-hydrogen bonders did not. The overall substituent effects were such that the activity of the unsubstituted compound was almost optimum.View full abstractDownload PDF (683K) -
SUGURU TAKATSUTO, NOBUO IKEKAWA1982 Volume 30 Issue 11 Pages 4181-4185
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(22R, 23R)-28-Homobrassinolide (18), an analog of brassinolide (1), was synthesized from stigmasterol (3).View full abstractDownload PDF (668K) -
YOSHIO HIROSE, YOSHIHISA SUEHIRO, YUMIKO FURUKAWA, TAKAO MURAKAMI1982 Volume 30 Issue 11 Pages 4186-4188
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe meltingpoint and infrared spectrum of synthesized 1, 6, 8-trihydroxy-3-hydroxymethylanthraquinone (II) were identical with those of citreoroseine (I) [ω-hydroxyemodin)-III)]. Synthesis of 1, 3-diacetoxy-3-bromomethyl-6-methoxyanthraquinone (VIII) was established. And fallacinal (V) could be prepared by oxidation of fallacinol (IV).View full abstractDownload PDF (451K) -
KAZUO NAGASAWA, TAKAO KANAIWA1982 Volume 30 Issue 11 Pages 4189-4191
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe 13C nuclear magnetic resonance chemical shifts for α-and β-carbons of simple thiacycloalkanes, namely thietane, thiolane, thiane and thiepane, have been completely and unambiguously assigned by using α, α-dideutero compounds ; the α-carbon signal, except for thietane, always appeared at lower field than that of the β-carbon.View full abstractDownload PDF (421K) -
HIDENOBU OHMORI, SHIRO NAKAI, HITOSHI MIYASAKA, MASAICHIRO MASUI1982 Volume 30 Issue 11 Pages 4192-4194
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSConstant current electrolysis of triphenylphosphine in acetonitrile containing an alcohol and benzoic or succinic acid in a one-compartment cell gave better yields of the title compounds than the previously reported controlled potential electrolysis in a divided cell. Constant voltage electrolysis was also found to be effective. The phosphonium salts reacted with carboxylic acids to form esters in high yields.View full abstractDownload PDF (387K) -
CHIAKI TANAKA, KEIKO NASU, NORIKO YAMAMOTO, MEGUMI SHIBATA1982 Volume 30 Issue 11 Pages 4195-4198
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe pyrolysis of benzyl 2-oxazolecarbamates (I) and benzyl 4-alkylallophanates (II) was investigated. Heating of benzyl 5-phenyl-2-oxazolecarbamate (Ia) at 230°C gave benzyl alcohol and 2-phenyl-6-(5-phenyl-2-oxazolyl)-5H-oxazolo [3, 2-α] [1, 3, 5] triazine-5, 7-(6H)-dione (IIIa). Compound IIIa was also obtained by heating the azide prepared from 5-phenyl-2-oxazolecarbohydrazide (IVa). In the same way, 2-methyl-6-(5-methyl-2-oxazolyl)-5H-oxazolo [3, 2-α] [1, 3, 5] triazine-5, 7 (6H)-dione (IIIb) and 2-phenyl-6-(5-phenyl-2-thiazolyl)-5H-thiazolo [3, 2-α] [1, 3, 5] triazine-5, 7 (6H)-dione (IIIc) were obtained from the corresponding hydrazides (IVb and IVc). Next, heating of benzyl 4-(2-phenylethyl)-allophanate (IIa) at 230°C gave cyanuric acid (VII), benzyl (2-phenylethyl) carbamate (VIII) and 1, 3-bis (2-phenylethyl)-1, 3, 5-triazine-2, 4, 6 (1H, 3H, 5H)-trione (IX).View full abstractDownload PDF (511K) -
HARUO SAIKACHI, TOKUJIRO KITAGAWA, HIDEAKI SASAKI, ALBERT M.VAN LEUSEN1982 Volume 30 Issue 11 Pages 4199-4204
Published: November 25, 1982
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTosylmethyl isocyanide (4) reacted readily with azole carbaldehydes, i.e., indole-2-carbaldehyde (8a), pyrazole-3 (5)-carbaldehyde (8b), 3 (5)-methylpyrazole-5 (3)-carbaldehyde (8c), 3 (5)-(2-furyl) pyrazole-5 (3)-carbaldehyde (8d), 1, 2, 4-triazole-3 (5)-carbaldehyde (8e), and tetrazole-5-carbaldehyde (8f), in the presence of an equimolar amount of potassium carbonate in refluxing methanol to yield the corresponding 5-substituted oxazoles (10 and 15b-f) as the final products. In the case of the reaction of 4 with imidazole-2-carbaldehyde (8g), however, N-(1-tosyl-1-alkenyl) formamide of type 18g, 1-amino-1-tosyl-2-alkene of type 19g, and 3-tosylimidazo [1, 2-c] pyrimidine (22g) were obtained, depending on the reaction conditions.View full abstractDownload PDF (618K)