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Volume 14, Issue 11
Displaying 1-21 of 21 articles from this issue
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Tohru Hino, Katsuko Tana-ami, Kazuko Yamada, Sanya Akaboshi1966 Volume 14 Issue 11 Pages 1193-1201
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTen kinds of N-substituted-2-(2-aminoethyl)thiopseudoureas (AETs) were prepared. 1'-Phenyl-AET (VI) gave 2-aminothiazoline derivative (XXIII) with one equivalent of alkali, while other AETs having at least one hydrogen atom at the amino nitrogen underwent intramolecular rearrangement to give MEGs. GEDs were prepared from these MEGs by mild oxidation. The NMR and IR spectra of these compounds were also discussed.View full abstractDownload PDF (968K) -
Tohru Hino, Katsuko Tana-ami, Kazuko Yamada, Sanya Akaboshi1966 Volume 14 Issue 11 Pages 1201-1209
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe cyclization of N-substituted 2-(2-aminoethyl)thiopseudoureas (AETs) to 2-aminothiazolines (2-Ats) was investigated. The AETs (I, II and III) having a substituent at the amino nitrogen afforded a simple 3-substituted 2-Ats. The phenyl derivative was cyclized easier than the corresponding methyl derivative. The AETs (VII and VIII) having a substituent at the nitrogen atom of the thiourea, however, afforded the mixture of products, IV (2-aminothiazoline) and a 2-(substituted-amino)-2-thiazoline. 2-Aminothiazoline (IV) was the main product in the case of methyl derivative (VII), while substituted 2-AT was the main product in the case of phenyl derivative (VIII). The AETs (XI and XII) in which the both nitrogens of thiourea were linked with two or three methylenes afforded 2-ATs (XII and XIV) without removal of an amine, and the free bases of these 2-ATs were unstable and underwent a rearrangement to give 2-(2-mercaptoethylamino)imidazoline or-tetrahydropyrimidine.View full abstractDownload PDF (1083K) -
Shigeharu Inouye1966 Volume 14 Issue 11 Pages 1210-1219
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe nuclear magnetic resonance spectra of methyl amino-hexopyranosides in the forms of free base, hydrochloride and N-acetate were measured in deuterium oxide and, in part, in pyridine. The spectrum of the free base showed a multiplet at higher field than 7 p.p.m., caused by weakly deshielding of an amino group. The analysis of this signal was shown to offer information in the vicinity of an amino group. The spectrum of the hydrochloride showed long-range deshielding of an anomeric proton along with other ring protons, possibly induced by the electric field of an ammonium cation. The long-range deshielding due to an acetamido group was weaker than an ammonium group. It was observed in a variety of the derivatives that H2 of α-glucopyranoses resonated at lower field with greater J1, 2 values than those of α-mannopyranoses. The differences presented ready distinction between the two isomers.View full abstractDownload PDF (1156K) -
Shiro Takahashi, Hideo Kano1966 Volume 14 Issue 11 Pages 1219-1227
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDeoxygenation of 1, 2-dimethylbenzimidazole 3-oxide (I) proceeded by treatment with phosphorus trichloride, sulfur dioxide, sodium hydrogensulfite and sodium borohydride besides by catalytic reduction with Raney nickel. The methyl group at C-2 of I seemed less reactive than that of the parent base and did not condense with benzaldehyde, p-dimethylaminonitrosobenzene or p-nitrobenzenediazonium chloride. However, I reacted with dimethyl oxalate in the presence of alkali to give 2-methoxalylmethyl-1-methylbenzimidazole 3-oxide in good yield. The reactions of I with acetic anhydride, benzoyl chloride, phosphoryl chloride, tosyl chloride, tosyl chloride-pyridine, potassium cyanide-benzoyl chloride, methyl cyanoacetate-acetic anhydride, phenyl isocyanate, phenyl isocyanide and isoamyl nitrite-sodium amide were examined. By these reactions, 2-substituted methyl-1-methylbenzimidazole and/or 6-substituted 1, 2-dimethylbenzimidazole were obtained. As a co-ordination compound, the boron trifluoride complex of I was obtained.View full abstractDownload PDF (1057K) -
Zen-ichi Horii, Takushi Kurihara, Shigeo Yamamoto, Ming-Ching Hsu, Chu ...1966 Volume 14 Issue 11 Pages 1227-1236
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEthyl trans-anti-, cis-anti-, and cis-syn-4-methyl-1, 2, 3, 4, 4a, 5, 6, 10b-octahydrobenzo[f]-quinoline-2-carboxylates (III, IV and V) were obtained by the reduction of ethyl 4-methyl-1, 2, 3, 4, 5, 6-hexahydrobenzo[f]quinoline-2-carboxylate (II), and their stereochemistries were discussed. Some derivatives of III, IV and V in which C2-ethoxycarbonyl group was replaced by carboxyl, diethylcarbamoyl, hydroxymethyl and methyl groups were also prepared.View full abstractDownload PDF (1120K) -
Isoo Ito, Taisei Ueda1966 Volume 14 Issue 11 Pages 1237-1241
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs a part of studies on syntheses of pyrazolone derivatives, 3-mercaptomethyl-2-methyl-4-substituted-1-phenyl-3-pyrazolin-5-one were prepared by the reaction of 3-bromomethyl-2-methyl-4-substituted-1-phenyl-3-pyrazolin-5-one with thiourea and alkaline treatment, the reduction of 1, 1-bis(2-methyl-4-substituted-5-oxo-1-phenyl-3-pyrazolin-3-yl)methyl disulfide and (2-methyl-4-substituted-5-oxo-1-phenyl-3-pyrazolin-3-yl)methyl thiocyanate.View full abstractDownload PDF (735K) -
Hiroshi Hikino, Kanji Meguro, Yojiro Sakurai, Tsunematsu Takemoto1966 Volume 14 Issue 11 Pages 1241-1249
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSExtraction of Zedoary (Curcuma zedoaria (Zingiberaceae)) has afforded a new sesquiterpenoid, curcumol, of the empirical formula C15H24O2. It has been shown to contain a vinylidene group and a hemiketal system. The guaiane carbon skeleton has been established by its dehydrogenation giving S-guaiazulene (IV). Curcumol has been ozonized to give the norketone (IX) which has been converted into the acid (X) and the lactone (XII). Spectroscopic study of these derivatives and other evidence show curcumol to be represented by formula I (R=H).View full abstractDownload PDF (1209K) -
Satoshi Mizukami, Koichi Nagata1966 Volume 14 Issue 11 Pages 1249-1255
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNineteen kinds of sodium thiohydroxamate (I) were synthesized from hydroxylamine and esters of thionic acids or dithioacids in the presence of sodium methylate with about 40% yields for the aliphatic compounds and above 70% yields for the aromatic ones with some exceptions. A number of sodium O-methylthiohydroxamate (II) were also obtained by the analogous method using O-methylhydroxylamine. On long standing. I were apt to rearrange to the 1, 3-disubstituted thiourea while II were very stable. Some crystalline thiohydroxamic acid and O-methylthiohydroxamic acids were prepared from I and II.View full abstractDownload PDF (783K) -
Koichi Nagata, Satoshi Mizukami1966 Volume 14 Issue 11 Pages 1255-1262
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe infrared spectra of some thiohydroxamic acids (I) and their deuterated compounds were investigated and compared with those of some O-methylthiohydroxamic acids (II). It was concluded that I exist in thione-form in the solid state but the both of thiol and thione tautomers exist in the liquid or in the solution, in which state polar solvents favor the former tautomer, whereas II occur in thiol-form in all the states. These facts were more positively confirmed by the NMR spectra and by the determinations of the pKa values. The "N-C=S bands" of the thione-form of I were assigned to the regions 1550±20, 1340±30 and 1085±5cm-1.View full abstractDownload PDF (864K) -
Koichi Nagata, Satoshi Mizukami1966 Volume 14 Issue 11 Pages 1263-1272
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThiohydroxamic acids react as thiol-form in aqueous solution, and gave S-alkyl and S, O-dialkyl derivatives, dibenzoyl derivatives, and the disulfides (I). Monobenzoyl derivatives were not obtained because of their instability. The structures of these derivatives were confirmed by the investigations of the infrared spectra. It was found that the S-S linkage of I are apt to cleave by alkali so that diacyl derivatives of I are easily rearragned to the corresponding isothiocyanate and 1, 3-dialkyl-2-thiourea. The mechanism of the rearrangement seemed to be analogous to that of the Lossen rearrangement.View full abstractDownload PDF (1120K) -
Eiji Ochiai, Makoto Takahashi1966 Volume 14 Issue 11 Pages 1272-1276
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn Fortsetzung der Versuche uber die Ableitung von 3-Indolessigsaureestern aus den entsprechenden Chinolin-Derivaten wurden nun 3-Indolessigsaure-Derivate direkt aus 4-Acylhydrocarbostyril-Derivaten mit guter Ausbeute abgeleited, indem man die letzteren mit 47%iger Bromwasserstoffsaure bzw. Konz. Chlorwasserstoffsaure erhitzt.View full abstractDownload PDF (667K) -
Issei Iwai, Norio Nakamura1966 Volume 14 Issue 11 Pages 1277-1286
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSβ-Bromocinnamonitrile and hydroxylamine afforded 3-amino-5-phenylisoxazole in the presence of alkali, unexpectedly. So the reaction of acetylenic nitriles and esters with hydroxylamine was examined under alkaline conditions. Phenylpropiolonitrile and propiolonitrile gave 3-amino-5-phenylisoxazole and 3-aminoisoxazole, respectively. Tetrolonitrile afforded a 3 : 1 mixture of 3-amino-5-methyl- and 3-methyl-5-amino-isoxazole in the presence of alkali. Under neutral conditions these nitriles gave the corresponding 5-aminoisoxazoles. Similarly, 3-hydroxy-, 3-hydroxy-5-methyl- and 3-hydroxy-5-phenyl-isoxazole were obtained from the corresponding acetylenic esters. In the case of methyl tetrolate, two isomers of tetrolohydroxamic acid were isolated as the intermediate. On the other hand, free phenylpropiolic acid gave only 3-phenyl-5-isoxazolone under the same alkaline conditions.View full abstractDownload PDF (1148K) -
Hidetoshi Yoshimura, Kazuta Oguri, Hisao Tsukamoto1966 Volume 14 Issue 11 Pages 1286-1290
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA simple and reliable identification method of morphine was developed by successive performance of color and fluorescent reactions with potassium platinum iodide reagent utilizing the same thin-layer chromatogram; after separation by thin-layer chromatography morphine could be identified as a violet-colored spot with above reagent and then reconfirmed as a blue fluorescent spot under ultraviolet light after the chromatogram was exposed to ammonia vapor. The fluorometric identification is based on the essentially same principal to that of Kupferberg, et al.1, 2), however the present method has certain advatages to identify morphine, especially excreted in urine, in respect of simplicity and reliability.View full abstractDownload PDF (692K) -
Hikaru Ozawa, Susumu Sato1966 Volume 14 Issue 11 Pages 1291-1297
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of [2-(methylphenylamino)ethyl]guanidine sulfate (MPG) on sympathetic nervous system was studied and the following results were obtained : 1) intravenous injection of MPG caused a fall of blood pressure and sustained contraction of the nictitating membrane in urethane anesthetized cat, 2) MPG caused a lasting depression of many excitatory responses, evoked by electrical stimulation of the peripheral sympathetic nerves, that is, inhibition of the response of the cat nictitating membrane to postganglionic sympathetic nerve stimulation and inhibition of the pressor responses in cat to the celiac ganglion or splanchnic nerve stimulation. In addition, these reduced responses were abolished by amphetamine, 3) MPG also caused the potentiation of the pressor responses to norepinephrine and epinephrine, but caused a potent antagonistic action to pressor responses produced by tyramine, dimethylphenyl-piperazinium and the occulusion of the carotid artery in cat, 4) injection of high doses of MPG caused a sympathomimetic effect on the cat nictitating membrance, the heart rate of cat and dog and the blood pressure in spinal cat. The contraction of the cat nictitating membrane by MPG was abolished by phentolamine and pretreatment with reserpine. From the results mentioned above, it is concluded that MPG has adrenergic neurone blocking action and sympathomimetic action resembling those of guanethidine and bretylium.View full abstractDownload PDF (883K) -
Hisashi Miyazaki, Yasuo Minaki, Yoshio Yoshimura1966 Volume 14 Issue 11 Pages 1298-1299
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
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Kinji Harada, Sakae Emoto1966 Volume 14 Issue 11 Pages 1300-1302
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
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Kazuhiko Araki, Setsuzo Tejima1966 Volume 14 Issue 11 Pages 1303-1306
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
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Hiroshi Hikino, Yojiro Sakurai, Hideji Takahashi, Tsunematsu Takemoto1966 Volume 14 Issue 11 Pages 1310-1311
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
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Shoji Hara, Tadashi Watabe, Yoshimasa Ike1966 Volume 14 Issue 11 Pages 1311-1314
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
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Masashi Hashimoto, Kiyoshi Hattori1966 Volume 14 Issue 11 Pages 1314-1316
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
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Chikara Kaneko, Ichiro Yokoe, Sachiko Yamada, Masayuki Ishikawa1966 Volume 14 Issue 11 Pages 1316-1319
Published: November 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (462K)
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