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YASUOKI MURAKAMI, YOICHI IITAKA
1969 Volume 17 Issue 12 Pages
2397-2404
Published: December 25, 1969
Released on J-STAGE: March 31, 2008
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Crystals of (-)-2-bromosuccinamic acid (C
4H
6O
3NBr) are orthorhombic, with space group P2
12
12
1 and lattice parameters a=7.70, b=9.23, c=8.88 A, containing four molecules in the unit cell. The structure was solved by the heavy atom method coupled with three-dimensional Fourier and difference Fourier synthese. The refinement was carried out by the full-matrix least-squares calculations. The final (R) value was 0.15. The absolute configuration was established to be (S) (-) by the anomalous dispersion method. The molecular and crystal structure were also discussed.
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TETSUZO KATO, MASAYUKI SATO
1969 Volume 17 Issue 12 Pages
2405-2410
Published: December 25, 1969
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N-Allylacetoacetamide (III) was heated in conc. H
2SO
4 to give 2-acetonyl-5-methyl-2-oxazoline (IVb). Acidic hydrolysis of IVb afforded isopropanolamine, acetone and carbon dioxide. N-(β-Hydroxyalkyl) acetoacetamide (X) was heated under reflux with thionyl chloride in chloroform to give N-(β-chloroalkyl) acetoacetamide (XI). Treatment of XI with methanolic KOH gave 2-acetonyl-2-oxazoline (IV). When the reaction of X with thionyl chloride was carried out at room temperature, 2, 3, 4, 5-tetrahydro-1, 4-oxazepin-5-one (XII) was obtained.
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TETSUZO KATO, HIROSHI YAMANAKA, JUNSHI KAWAMATA
1969 Volume 17 Issue 12 Pages
2411-2416
Published: December 25, 1969
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Acylation of β-aminocrotonamide (I) with α, β-unsaturated acid anhydride (e. g. acrylic, crotonic and methacrylic anhydrides) afforded 2-methyl-6-oxo-1, 4, 5, 6-tetrahydro-pyridine-3-carboxamide derivatives (IV), which were easily dehydrogenated by heating with Pd-black to give 2-methyl-6-oxo-1, 6-dihydropyridine-3-carboxamides. Similarly, acylation of primary enamines such as ethyl β-aminocrotonate (XIa), 4-amino-3-penten-2-on (XIb), 2-amino-1-propenyl phenyl ketone (XIc), and 2-aminocrotononitrile (XId) with acrylic anhydride afforded 5-substituted-6-methyl-3, 4-dihydro-2-pyridones (XII), which were given by the reaction of the primary enamines (XI) with ethyl acrylate in the presence of sodium ethoxide.
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YUKICHI KISHIDA, ATSUSUKE TERADA
1969 Volume 17 Issue 12 Pages
2417-2423
Published: December 25, 1969
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Treatment of ethyl plopiolate (I) with diethyl acetamidomalonate (II) gave cyclized product, 1-acetyl-2-oxo-5, 5-diethoxycarbonyl-3-pyrroline (III). Analogously, III was obtained from ethyl cis-β-chloroacrylate (VIII) and the same reagent in good yield. VIII was treated with ethyl acetamidocyanoacetate (XIII) and diethyl carbobenzyloxyaminomalonate (XIV) to afford cyclized products, 1-acetyl-2-oxo-5-cyano-5-ethoxycarbonyl-3-pyrroline (XVII) and 1-carbobenzyloxy-2-oxo-5, 5-diethoxycarbonyl-3-pyrroline (XVIII), respectively. On the other hand, the reactions of VIII with diethyl benzamidomalonate (XV) and diethyl trifluoroacetamidomalonate (XVI) afforded open chain products, diethyl 4-benzamido-4-ethoxycarbonylglutaconate (XIX) and diethyl 4-trifluoroacetamido-4-ethoxycarbonylglutaconate (XX), respectively.
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YUKICHI KISHIDA, NORIO NAKAMURA
1969 Volume 17 Issue 12 Pages
2424-2435
Published: December 25, 1969
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The addition reaction of diethyl acetamidomalonate anion to ethyl α, β-dibromoacrylate (I) and base catalyzed reactions of the adduct, diethyl 4-acetamido-2-bromo-4-carbethoxytrans-glutaconate (IIIb), were described. Addition of bromine to ethyl propiolate in carbon tetrachloride or acetic acid gave exclusively ethyl cis-α, β-dibromoacrylate (Ia). The reaction of both Ia and ethyl trans-α, β-dibromoacrylate (Ib) with diethyl acetamidomalonate anion gave the same product IIIb. Treatment of IIIb with sodium amide or potassium t-butoxide gave ethyl 2-bromo-3-(5-ethoxy-2-methyl-4-oxazolyl) acrylate (VIII). The reaction of IIIb with sodium ethoxide afforded diethyl 4-acetamido-4-ethoxy-trans-glutaconate (XVIII). The structures of VIII and XVIII were proved.
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HIDEAKI SHIRAI, TAMOTSU YASHIRO, ICHITOMO MIWA
1969 Volume 17 Issue 12 Pages
2436-2441
Published: December 25, 1969
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1, 3-Diphenyl-5-butylhydantoin (I) was synthesized by two methods, indirect and direct, with the object of the development of a new analgesic agent. In the course of the indirect method, treatment of 1, 3-diphenyl-2-thiohydantoin (IV) with n-butylaldehyde gave 1, 3-diphenyl-5-butylidene-2-thiohydantoin (V) as two kinds of crystals, which were confirmed to be geometrical isomers with each other. The configurations of them were determined from the NMR spectral data. Two by-products obtained in this reaction was also geometrical isomers with each other, and they were deduced to be dimers of 1, 3-diphenyl-5-butylidene-2-thiohydantoin, 1, 3-diphenyl-5-{β-ethyl-γ-(1, 3-diphenyl-2-thiohydantoinyl)} hexylidene-2-thiohydantoin (Xa and Xb) from some physical data. In the direct method, 1, 3-diphenyl-5-butylhydantoin was obtained in 40% yield by refluxing 2-anilinohexanoic acid (IX) and phenyl isocyanate in xylene.
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KAZUO TOMITA, MITSUO NAGANO
1969 Volume 17 Issue 12 Pages
2442-2447
Published: December 25, 1969
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In the reaction of α-acetylenic alcohol and carbon disulfide, three compounds (4-alkylidene-1, 3-oxathiolane-2-thione, -1, 3-dithiolane-2-thione and -1, 3-oxathiolane-2-one) were obtained. In this paper it became clear that the formation of two compounds (V and VI) of them was due to the reaction of sodium α-acetylenyl xanthate (III) and IV by using 3-phenyl-2-propyn-1-ol. New 4-alkylidene-1, 3-dithiolane-2-thiones (XXIV and XXVI) were easily prepared from 4-alkylidene-1, 3-oxathiolane-2-thiones (XXIII and XXV) and commercially available potassium xanthate.
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MASAMICHI FUKUOKA, HIROSHI MITSUHASHI
1969 Volume 17 Issue 12 Pages
2448-2454
Published: December 25, 1969
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A new pregnane, stephanol, was isolated from Stephanotis japonica (Asclepiadaceae), and its chemical and physicochemical studies suggest the allocation of its structure.
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SABURO ISHIWATA, YOUICHI SHIOKAWA
1969 Volume 17 Issue 12 Pages
2455-2460
Published: December 25, 1969
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Reactions of 5-aminobenzimidazoles (I) with each crotonaldehyde and methyl propenyl ketonl selectively provided 3H-imidazo [4, 5-f] quinoline derivatives (type-A), whereas reaction of I with ethyl acetoacetate gave a mixture of 3H-imidazo [4, 5-f]-(type-A) and 1H-imidazo [5, 4-g] quinoline derivative (type-B). This result was explained by the stability of σ complex of intermediate.
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SADAO OIDA, EIJI OHKI
1969 Volume 17 Issue 12 Pages
2461-2474
Published: December 25, 1969
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Cycloaddition reaction of N-(p-methoxyphenyl)-1-benzyl-2, 3-aziridinedicarboximide (8) with dimethyl acetylenedicarboxylate (3) was not effected thermally, but under irradiation it resulted in a formation of 1 : 1-cycloadducts, I (9), II (17), and III (34), and a 1 : 2-cycloadduct IV (38). The structural determination of these cycloadducts was made from their spectral data and chemical degradations. Further, mutual photochemical transformation of the cycloadducts was also verified.
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NOBUYASU MIZUNO, AKIRA KAMADA, NOBORU YATA, MASARU AOKI
1969 Volume 17 Issue 12 Pages
2475-2483
Published: December 25, 1969
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Pyridoxine 3, 4-dipalmitate (PIN-DP), insoluble in water, was little absorbed in man following oral administration of suspension in water or aqueous Tween 80. But, the absorption increased markedly with a solubilized solution with Tween 80. Previously, it was found that PIN-DP failed to permeate the intestinal tract unlike pyridoxine (PIN) which was the hydrolyzed product of ester in the tract. Hydrolysis of PIN-DP solubilized with Tween 80 increased ten times with the addition of sodium taurocholate or glycocholate. But, no increase was observed with the addition of sodium lauryl sulfate or bis (2-ethylhexyl) sulfosuccinate. PIN permeated through the everted sac of rat intestine following the addition of sodium taurocholate and lipase to a solubilized Tween 80 solution of PIN-DP.
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SADAO OHKI, MITSUO AKIBA
1969 Volume 17 Issue 12 Pages
2484-2487
Published: December 25, 1969
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6, 7-Cyclobutano-1, 2-cyclopropanoquinolizidine (I) (9-azasteroid ring system) and perhydrodibenzo [c, f] quinolizine (II) (9-aza-D-homosteroid) were synthesized by the routes shown in Chart 1 and 3.
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YASUHIRO YAMANE, KAZUO SAKAI, ISAO UCHIYAMA, MISUE TABATA, NORIKO TAGA ...
1969 Volume 17 Issue 12 Pages
2488-2493
Published: December 25, 1969
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The effect of basic cupric acetate on the activities of the drug metabolizing enzymes was studied. When basic cupric acetate was administered with and without DAB to the rat, the overall activity of the DAB metabolizing enzyme system was increased remarkably, which was mainly ascribed to the enhancement of the azo-reduction. The activity of azo-reduction was reduced a little by the administration of DAB alone. The activity of N-demethylation was reduced a little by the administration of copper, but by the administration of DAB alone the activity appeared to increase a little. The administration of copper and DAB did not affect the activity of aromatic hydroxylation. One role of copper which retards the hepatic carcinogenesis by DAB might be related to the enhancement of the activity of azo-reduction, which detoxicates the carcinogenic dye to the noncarcinogenic compounds.
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TORAHIKO KISHIKAWA
1969 Volume 17 Issue 12 Pages
2494-2501
Published: December 25, 1969
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Direct condensation of D-glucuronolactone with o-nitroaniline (Ia) or 5-nitro-o-4-xylidine (Ib) afforded o-nitroanilino-or 5-nitro-o-4-xylidino-D-glucuronolactone, IIa or IIb in an excellent yield. On treatment with ammoniacal MeOH, IIa and IIb were amidated to give VIIa and VIIb, respectively. It was found that they held a furanose structure. VIIa and VIIb underwent conversion of the lactol ring from furanoside to pyranoside form by the presence of AcOH, affording o-nitroanilino-and 5-nitro-o-4-xylidino-D-glucopyranuronamide, XIa and XIb. Hydrogenation of the nitro group in the acetylated derivative XIIa or XIIb was effectively made over a palladium or platinum catalyst. Ring closure of the phenylenediamine derivative XIIIa or XIIIb with ethyl orthoformate or ethyl formimidate hydrochloride followed by acid or alkali hydrolysis gave 1-deoxy-1-(1-benzimidazolyl)-or 1-deoxy-1-(5, 6-dimethyl-1-benzimidazolyl)-β-D-glucopyranuronamide, XVa or XVb. The corresponding benzimidazole nucleosides of D-glucuronolactone and D-glucofuranuronamide could not be obtained by the same ring closure procedure. XVa, XVb and 1-deoxy-1-(5, 6-dichloro-1-benzimidazolyl)-β-D-glucopyranuronamide (XVc) were also formed by the chloromercury method of Davoll and Brown.
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GENZO OKUSA, MICHIKO KUMAGAI, TAKANOBU ITAI
1969 Volume 17 Issue 12 Pages
2502-2506
Published: December 25, 1969
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A reaction of pyridazine 1-oxide with Grignard reagents prepared from bromobenzene, p-bromotoluene, o-bromotoluene, m-bromotoluene, p-bromoanisol and o-bromoanisol, gave the corresponding 1-aryl-trans-1-butene-3-yne (III) in about 30% yields. These structures were determined by in frared and nuclear magnetic resonance spectroscopy.
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SHUNICHI NAITO, KOICHI NAKAMICHI
1969 Volume 17 Issue 12 Pages
2507-2514
Published: December 25, 1969
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A new compression fixture was designed for the measurement of the state of binding between a tablet surface and punch face. It was found by the use of this device that the ability of a material to form a"good"or"bad"tablet may be predicted from two factors ; the slipping force of a tablet surface and passive pressure of a lower punch. The results of measurement were also compared with tableting troubles that occur during a large-scale operation.
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SHIGERU GOTO, YOSHIYUKI HIRAKAWA, SADAO IGUCHI
1969 Volume 17 Issue 12 Pages
2515-2525
Published: December 25, 1969
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The influence of pH on the conversion of diacetylacetone in aqueous solution and its mechanistic pathway were investigated in detail. And it was concluded that diacetylacetone converts completely to 2, 6-dimethyl-4-pyrone in acidic region (pH-5), the main reaction in neutral region (pH 5-10), the intermolecular condensation of undissociated diacetylacetone, is catalyzed by specific base, general acid and base (buffer components), and diacetylacetone decomposes via a parallel reaction path involving acetylacetone and acetoacetate as the important intermediates in lower alkaline region. A kinetic approach was quite effective for investigation in alkaline region.
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TAKAICHI ARITA, RYOHEI HORI, EIJI OWADA, KATSUYUKI TAKAHASHI
1969 Volume 17 Issue 12 Pages
2526-2532
Published: December 25, 1969
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In order to understand the renal excretion mechanisms of sulfonamides, some renal clearance studies were undertaken with two sulfonamides, sulfanilamide and sulfisoxazole, in rabbits. From the results of inhibitory experiments by iodopyracet, it was found that only sulfisoxazole was actively secreted into the tubule by p-aminohippurate mechanism. Using this method it becomes possible to calculate and separately estimate the net amounts secreted and reabsorbed. The result calculated with sulfisoxazole suggested a significant amount secreted and a higher amount reabsorbed.
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SHIRO TERASHIMA, KONGKO LEE, SHUNICHI YAMADA
1969 Volume 17 Issue 12 Pages
2533-2539
Published: December 25, 1969
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The absolute configuration of (+)-2-cyano-2-methyl-3-phenylpropionic acid (Ia), an important compound for the investigation of reaction mechanisms, was elucidated as (S)-series by chemical correlation with (S) (+)-α-methyl-α-isopropylsuccinic acid ((S) (+)-III), whose absolute configuration is already established. During the correlation, (+)-2-isopropyl-2-methyl-3-phenylpropionic acid ((+)-VII) was also confirmed as belonging to (R) series. Preliminary experiments on racemic compounds are described in detail in the experimental section.
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KONGKO LEE, SHIRO TERASHIMA, KAZUO ACHIWA, SHUNICHI YAMADA
1969 Volume 17 Issue 12 Pages
2540-2547
Published: December 25, 1969
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Hofmann and Curtius rearrangements of (S) (+)-2-cyano-2-methyl-3-phenylpropionic acid ((S) (+)-Ia) having a quarternary asymmetric carbon at α position were made. These rearrangements clearly proceeded with nearly 100% retention of configuration even if the migrating groups were quarternary. Preliminary examinations using racemic compounds are also described.
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HIROKO(SASAKI) TODA, HIROSHI SUGIYAMA, SHUICHI SETO
1969 Volume 17 Issue 12 Pages
2548-2553
Published: December 25, 1969
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The synthesis of 3-aminotropone (III) which is one of the fundamental troponoid series aromatic compounds and has not never been synthesized was carried out, and optimal conditions of the ammonolysis of 3-tosyloxytropone (II) were taken in the following ; solvent, isopropanol ; reaction temperature, 45-50° ; reaction time, about 80 min. It was found that bromination of III afforded 3-amino-2-bromotropone (IV) or known 2-bromo-3-hydroxytropone (V), depending on the conditions. The structure of IV was elucidated from a comparison of the NMR spectra of III and IV. Treatment of III with dimethyl sulfate gave 3-methoxytroponeimine (VI), which was isolated as picrate (VII). N-Acetyl derivative (VIII) of III was given by heating of III with acetic anhydride.
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IKUO MORIGUCHI, NOBUYOSHI KANENIWA
1969 Volume 17 Issue 12 Pages
2554-2557
Published: December 25, 1969
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Charge-transfer properties of 12 sulfonamides, together with diaminodiphenyl sulfone, p-aminobenzoic acid, and aniline, were investigated by their interactions with p-chloranil. The equilibrium constant was determined and the ionization potential (I
D) was estimated by utilizing the charge-transfer band arising in the 500-550 mμ region. The relation of hv
CT (charge-transfer transition energy) or I
D to the Michaelis constant for the acetylation of sulfonamides with liver extract indicated that the affinity of the drugs to acetylation enzymes increased as the ability of the charge-transfer of the drugs increased. The relationships between hv
CT or I
D and in vitro bacteriostatic activities were expressed with parabolic curves, which indicated the optimum value of I
D being about 2.37 eV for the potent sulfonamides. The relationships were explained from the dependence of the affinity to enzymes on the charge-transfer ability of the drugs.
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NOBUHARU KAKEYA, NOBORU YATA, AKIRA KAMADA, MASARU AOKI
1969 Volume 17 Issue 12 Pages
2558-2564
Published: December 25, 1969
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Hansch-Fujita's method was applied to a structure-activity analysis of 22 sulfonamide derivatives with an inhibitory activity against carbonic anhydrase. Electronic parameters such as Hammett's σ factor, △pK
a, △ppm and △fr, and hydrophobic parameters such as π, π
c and β were employed. △pK
a, △ppm, △f
rπ, π
c and β were derived from dissociation constant, NMR chemical shift of sulfamoyl protons, S=O valence-force constant, n-octyl alcohol-water partition coefficient, chloroform-water partition coefficient and association constant to albumin, respectively. This analysis proved to be useful in predicting not only the activity of substituted benzenesulfonamides except o-substituted derivatives, but also that of 1, 3, 4-thiadiazole-5-sulfonamide derivatives. The activity of o-substituted derivatives was satisfactorily predicted with the use of polar parameter σ and steric constant E
s.
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MASAYUKI ONDA, KYOKO YONEZAWA, KAORU ABE
1969 Volume 17 Issue 12 Pages
2565-2570
Published: December 25, 1969
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When anhydromethylberberine derived from α-allocryptopine was treated with dilute hydrochloric acid, it gave three products, whose structures were identified to contain the spiro-type skelton instead of"Perkin's compound"by the nuclear magnetic resonance spectroscopy.
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SUSUMU ISHIGURO, MASAKATSU SAKATA, MASANOBU HAGA, SETSUZO TEJIMA
1969 Volume 17 Issue 12 Pages
2571-2580
Published: December 25, 1969
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1, 2-Di-S-acetyl-3, 4, 6-tri-O-acetyl-β-D-mannopyranose (X) and methyl 1, 2-dithio-2-S-methyl-3, 4, 6-tri-O-acetyl-β-D-mannopyranoside (XI) were synthesized using an unequivocal route. A detailed comparison of the physical constants and NMR data of X with those of 1, 2-di-S-acetyl-3, 4, 6-tri-O-acetyl-β-D-mannopyranose, which had been reported from our laboratory (H. Nakamura, S. Tejima, M. Akagi, Chem. Pharm. Bull. (Tokyo), 14, 648 (1966).) clarified that the previous compound (VI) was the α-anomer of X. The corresponding methyl 1, 2-dithio-2-S-methyl-3, 4, 6-tri-O-acetyl-α-D-mannopyranoside (VII) was prepared from VI. Reaction of potassium thiolacetate with 2-O-mesyl-3, 4, 6-tri-O-acetyl-β-D-glucopyranosyl N, N-dimethyldithiocarbamate (XVI) afforded three products (XVII, XVIII, VIII) in proportions of 5 : 2 : 3. The structure of the main product (XVII), which had been assigned as 1, 2-dithio-1-N, N-dimethyldithiocarbamoyl-2-S-acetyl-3, 4, 6-tri-O-acetyl-β-D-mannopyranose (S. Ishiguro, S. Tejima, Chem. Pharm. Bull. (Tokyo), 15, 1478 (1967).), was corrected to 1, 2-dithio-1-S-acetyl-2-N, N-dimethyldithiocarbamoyl-3, 4, 6-tri-O-acetyl-β-D-mannopyranose. The by-products, XVIII and VIII, were assigned as 2-N, N-dimethyldithiocarbamoyl-2-deoxy-3, 4, 6-tri-O-acetyl-D-arabino-hexopyranose-1-ene and 1, 2-dideoxy-1, 2-trithiocarbonyl-3, 4, 6-tri-O-acetyl-β-D-mannopyranose, respectively. The reaction mechanisms on the facile substitution of secondary mesyl in thiosugars, which may be more reasonable than before, were discussed.
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AKIHIRO YAMAZAKI, TADAOMI SAITO, YOSHITAKA YAMADA, IZUMI KUMASHIRO
1969 Volume 17 Issue 12 Pages
2581-2585
Published: December 25, 1969
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2, 6-Dichloro-9-(2, 3, 5-tri-O-acetyl-β-D-ribofuranosyl) purine (I), when treated with 0.5 N barium hydroxide, afforded 2-chloroinosine (II), which was also obtained by reaction of I with 2 moles of methanolic sodium hydroxide followed by alkaline hydrolysis via 6-methoxy derivative (IV). Compound II was converted with sodium methoxide to 2-methoxyinosine (V). Alternatively, V was prepared by treating of I with the excess of methanolic sodium hydroxide. Compound V was allowed to react with acetone in the presence of 2, 2-dimethoxypropane and then phosphorylated with phosphoryl chloride to give, after deacetonation, 2-methoxyinosine 5'-phosphate (VIII). The synergistic flavoring strength of VIII with monosodium L-glutamate (MSG) was evaluated as an analog of 2-methylthioinosine 5'-phosphate or xanthosine 5'-phosphate. Similarly, 2-chloroinosine 5'-phosphate (IX) was synthesized from II and its flavoring strength was evaluated.
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TAICHIRO KOMENO, SHOICHI ISHIHARA, KIYOKO TAKIGAWA, HIKARU ITANI, HIKO ...
1969 Volume 17 Issue 12 Pages
2586-2598
Published: December 25, 1969
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Extension on the cyclization reaction of a steroidal 6α-acetylthio-4-en-3-one by treatment of sodium hydride, giving a methyl thiophene fused at C
4, C
5, and C
6, was studied. Similar cyclization of 6α-acetoxy-and 6α-acetylamino-4-en-3-one, yielding a methylfuro-and a methylpyrrolo compound, respectively, was observed in considerable yield. The more facile cyclization was found in 6α-benzoyloxy-and 6α-benzoylthio-4-en-3-one. The structure of the former, 6-phenylfuro compound, was established chemically by the oxidation to an ene-dione (VI). In addition, benzenosteroids fused at C
4, C
5, and C
6 were also synthesized.
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TOSHIO NAMBARA, HIROSHI HOSODA, TOSHIYUKI SHIBATA
1969 Volume 17 Issue 12 Pages
2599-2603
Published: December 25, 1969
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The reaction mechanism of lithium aluminum hydride reduction was investigated with the 13α-steroidal 16, 17-bromohydrins by means of tracer technique. The epimeric cis-bromohydrins were primarily led to the ketone resulting from hydride shift and then further reduced to the 17-hydroxylic compounds, where"mixed hydride"produced from the released bromide and lithium aluminum hydride would play a role of reducing agent. On the other hand the trans-bromohydrin was reduced to the corresponding alcohol by direct displacement of the halogen with hydride. Based upon these experimental results feasibility of the pathway involving reduction of the halohydrin in the five-membered ring has been discussed.
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TAICHIRO KOMENO, HIROKO WAKABAYASHI, HIKOZO IWAKURA
1969 Volume 17 Issue 12 Pages
2604-2607
Published: December 25, 1969
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5'-Methylfuro [4', 3', 2'-4, 5, 6] pregn-5-ene-3, 20-dione was treated with maleic anhydride, dimethyl acetylenedicarboxylate, dimethyl fumarate and benzyne, respectively, to yield the 1 : 1 adducts. The stereochemistry of these adducts was studied and the unexpected β-attack by the dienophiles was deduced from the NMR data.
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1969 Volume 17 Issue 12 Pages
2608-2613
Published: December 25, 1969
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YOSHIRO KOBAYASHI, ITSUMARO KUMADAKI, HARUO SATO
1969 Volume 17 Issue 12 Pages
2614-2619
Published: December 25, 1969
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The Reissert reaction with 1, 6-naphthyridine occurs at the nitrogen atom of 6-position. In the same reaction with 1, 6-naphthyridine 1-oxide, 6-oxide, and 1, 6-dioxide, N-oxide group reacts and gives 2-cyano-, 5-cyano-, and 2, 5-dicyano-derivatives as expected. And 1, 6-dioxide reacts with KCN in MeOH to give 2-methoxy-5-cyano-1, 6-naphthyridine, 2-methoxy-1, 6-naphthyridine-5-carboxamide, 2-methoxy-1, 6-naphthyridine 6-oxide. The same recation with 1-oxide gives 1, 6-naphthyridine and 2-methoxy-1, 6-naphthyridine or 2-methoxy-1, 6-naphthyridine-5-carboxamide. The mechanism of these novel reactions was proposed.
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SHOJI KOJIMA, HISASHI ICHIBAGASE
1969 Volume 17 Issue 12 Pages
2620-2625
Published: December 25, 1969
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1969 Volume 17 Issue 12 Pages
2625-2628
Published: December 25, 1969
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KOJI HAYASHI, ATSUKO NAKAO, HIROSHI MITSUHASHI
1969 Volume 17 Issue 12 Pages
2629-2632
Published: December 25, 1969
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