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Tatsuo Ohta, Yo Mori, Masuo Umeda
1959 Volume 7 Issue 5 Pages
547-549
Published: July 20, 1959
Released on J-STAGE: March 31, 2008
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The reexamination of the φ-dictamnine synthesis was carried out. The reaction of (II) with cyanoacetic acid in alkaline medium proceeded mainly to the dicarboxylic acid (IIIc). According to the present and previous experiments, it was concluded that φ-dictamnine obtained by Asahina and Inubuse was possibly an impure compound mixed with (X).
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Eiji Ochiai, Toshihiko Okamoto
1959 Volume 7 Issue 5 Pages
550-556
Published: July 20, 1959
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The presence of α-methylenecyclohexanol grouping in ignavine or des-N-methyl-anhydroignavinol was proved by rearrangement reaction to ketone. Oxidative cleavage of the cyclohexanol ring in des-N-methylanhydroignavinol gave a dicarboxylic and one of the carboxyl groups in this acid was confirmed as tertiary. α-Glycol group which is another functional group in des-N-methylanhydroignavinol was also cleaved by oxidation to give a dicarboxylic acid and the glycol was proved to exist at carbons γ ond δ to the nitrogen.
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Eiji Ochiai, Toshihiko Okamoto
1959 Volume 7 Issue 5 Pages
556-559
Published: July 20, 1959
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The results of dehydrogenation of anhydroignavinol and oxidation of des-N-methyl-anhydroignavinol are discussed and tentative structures for anhydroignavinol and ignavine are presented.
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Eiji Ochiai, Masayuki Ishikawa
1959 Volume 7 Issue 5 Pages
559-566
Published: July 20, 1959
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Der Bromcyan-Abbau des 2'-Oxo-9-benzoylhexahydrochinins (I) sowie seines Alloisomers auf der Konfiguration von C-4'wurde durchgefuhrt. Bei beiden Fallen wurde die Bindung zwischen dem Stickstoff und dem C-6-bzw. C-2-Kohlenstoffatom des Chinuclidinkerns gespalten. Die beiden Spaltprodukte aus (I) wurden in die Verbindungen ubergefuhrt, die 10-Methoxydihydrocorynanthean und 2-(1-Methylpropyl)-9-methoxy-1, 2, 3, 4, 6, 7, 12, 12b-oktahydro [2, 3-a] chinolizin oder ihren Stereoisomeren entsprechen.
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Tetsuji Kametani, Keiichiro Fukumoto, Toyoyuki Katagi
1959 Volume 7 Issue 5 Pages
567-572
Published: July 20, 1959
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The Eschweiler-Clarke and Pictet-Spengler reactions of β-methoxysafrylamine were examined. In the former reaction N, N-dimethyl-β-methoxysafrylamine was obtained in place of expected isoquinoline, but in the latter reaction four kinds of isoquinoline derivatives were formed according to reaction conditions of time and temperature. When heated for 30 minutes with formaldehyde solution, 3-methyl-1, 2-dihydro-(IV) and 3-methyl-4-methoxy-1, 2, 3, 4-tetrahydro-6, 7-methylenedioxyisoquinoline (III) were obtained, while 2, 3-dimethyl-1, 2-dihydro-(VII) and 2, 3-dimethyl-1, 2, 3, 4-tetrahydro-6, 7-methylene-dioxyisoquinoline (VI) were obtained when heated for 7 hours. Especially in the latter case, it is interesting that 4-methoxy derivative is obtained only by heating with formaldehyde solution although it could not be synthesized by the Bischler-Napieralski reaction and that, in addition, the substance (VII) was obtained very easily by way of (VI).
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Hiroyuki Inouye, Yoshikiyo Kanaya, Yorihiko Murata
1959 Volume 7 Issue 5 Pages
573-580
Published: July 20, 1959
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1) Es wurde erwiesen, dass verschiedene p-Hydroxyphenylather durch die Einwirkung des Gibbs'schen Reagenz (I), unter der Abspaltung der para-standigen RO-Gruppe als ROH, Indophenol-Korper bilden. So wurde der Chemismus der Farbreaktion von Homoarbutin (V) und Pirolatin (VI) durch dieses Reagenz klargestellt. 2) Es wurde erwiesen, dass p-Hydroxybenzylamin (IX) und dessen sekundares (X) sowie tertiares Amin (XI) bei der Einwirkung des Reagenz (I), unter der Abspaltung der-CH
2NRR'Gruppe als Amin (Ammoniak bei (IX)) und Formaldehyd, Indophenol-Korper bilden. Auf Grund dieser Tatsachen wurde der Chemismus der durch dieses Reagenz bewirkten Farbreaktion von Tetrahydrojatrorrhizin (XIII), N, 4'-Dimethylisococlaurin (XIV) und 4'-Methylisococlaurin (XV) erortert. 3) Es wurde weiter erwiesen, dass p-Chlorphenol und p-Hydroxybenzoesaure auch in gleicher Weise Indophenol-Korper liefern.
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Itiro Yosioka, Shizue Arafune
1959 Volume 7 Issue 5 Pages
581-584
Published: July 20, 1959
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Bromination of phenazine N-oxide, and 1-and 2-methoxyphenazine was carried out and 1-methoxy-4-bromo-and 1-bromo-2-methoxy-phenazines were obtained, but bromo derivative of phenazine N-oxide was not formed. Bromination of 1-methoxyphenazine 5-oxide and 2-methoxyphenazine 5-and 10-oxides was also carried out and each of their bromo derivatives was prepared.
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Haruo Saikachi, Keizo Suzuki
1959 Volume 7 Issue 5 Pages
584-588
Published: July 20, 1959
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Twenty-six new 2-methyl-3-(5-nitro-2-furyl) acrylamides and six esters were prepared by condensation of 2-methyl-3-(5-nitro-2-furyl) acryloyl chloride and various amines or alcohols. Antibacterial activity of these derivatives is discussed.
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Yuichi Kanaoka
1959 Volume 7 Issue 5 Pages
589-594
Published: July 20, 1959
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Varied aliphatic non-cyclic amines (II∼X) were prepared and oxidized in the hope of elucidating some fundamental aspects of the Robinson dehydrogenation reaction. In the case of tertiary amines the cyclization was brought about most smoothly, whereby five-membered ring was likely to be formed preferentially over a six-membered one. In secondary amines, yields were varied presumably due to side or secondary reactions, while primary amines were shown to be unsuitable for this reaction.
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Yuichi Kanaoka
1959 Volume 7 Issue 5 Pages
595-597
Published: July 20, 1959
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3-Substituted tetrahydroisoquinoline (VII) was oxidatively cyclized to form dibenzo-quinolizine derivative (IV). Some related aspects of the Robinson dehydrogenation reaction were discussed.
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Yuichi Kanaoka
1959 Volume 7 Issue 5 Pages
597-601
Published: July 20, 1959
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In the course of extensive studies on the Robinson dehydrogenation reaction, 1-(3, 4-dihydroxybenzyl)-and 1-(3, 4-dihydroxyphenethyl)-1, 2, 3, 4-tetrahydro-β-carbolines (III and VI) and their N-methyl derivatives (V and VII) were oxidized. Though (III) and (V) failed in giving any definite result, (VI) and (VII) gave the same oxidation product (XI), to which was assigned the structure (II) involving additional unsaturation.
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Torizo Takahashi, Fumiro Yoneda, Ryota Oishi
1959 Volume 7 Issue 5 Pages
602-604
Published: July 20, 1959
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N-Substituted imidazo [b] pyridines having substituent in 3-position were prepared.
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Genzo Ito, Yoshihisa Shibanuma
1959 Volume 7 Issue 5 Pages
605-608
Published: July 20, 1959
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Funf Guanidin-und elf Pyrimidin-derivate mit Diphenylatherkern wurden synthetisiert und ihre in vitro-Wirksamkeit gegen Tuberkelbazillen wurde gepruft.
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Yoshio Ban, Osamu Yonemitsu, Takeshi Oishi, Susumu Yokoyama, Masako Na ...
1959 Volume 7 Issue 5 Pages
609-615
Published: July 20, 1959
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It was proved that the reaction of each of 1-phenethyl-2 (1H)-pyridone, 1-(3, 4-methyl-enedioxyphenethyl)-2 (1H)-pyridone, and 1-(3, 4-dimethoxyphenethyl)-2 (1H)-pyridone with phophoryl chloride gave the corresponding 2-chloropyridinium salt and not the cyclized product in every case. On being treated with dilute aqueous sodium hydroxide solution at a room temperature, these 2-chloropyridinium salts yielded the corresponding pyridones, which had been described as the ring cleavage of benzo [a] quinolizinium salts induced with various basic reagents.
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Seishi Takagi, Hiroaki Tsukatani, Kyozo Hayashi
1959 Volume 7 Issue 5 Pages
616-618
Published: July 20, 1959
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DL-2-Amino-3-guanidinopropionic acid was prepared in a fairly good yield from DL-2, 3-diaminoprorionic acid by treatment with S-methylisothiourea sulfate after protection of the amino proups in 2-and 3-positions respectively with benzoyl and benzyloxycarbonyl group.
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Seishi Takagi, Hiroaki Tsukatani, Kyozo Hayashi
1959 Volume 7 Issue 5 Pages
619-621
Published: July 20, 1959
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L-2-Amino-4-guanidinobutyric acid was prepared in a fairly good yield from L-2, 4-diaminobutyric acid by treatment with S-methylisothiourea sulfate after converting the acid to its copper salt and protecting the amino groups in 2-and 4-positions respectively with benzoyl and benzyloxycarbonyl group.
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Goro Chihara, Nanase Kurosawa, Etsuji Takasaki
1959 Volume 7 Issue 5 Pages
622-627
Published: July 20, 1959
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Analytical method for various urinary calculi through infrared spectral measurement was established.
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Atsuji Okano, Kazuhiko Hoji, Tosaku Miki, Akio Sakashita
1959 Volume 7 Issue 5 Pages
627-634
Published: July 20, 1959
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Digitalinum verum hexaacetate, hexapropionate, and monoacetyl pentapropionate were submitted to deacylation with potassium hydrogen carbonate under suitable conditions and these acyl derivatives were converted to diacyl derivatives possessing one acyl group each in the 16-position of gitoxigenin and in the digitalose portion. Some examinations were made on the properties of the newly formed derivatives.
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Kazuo Miyatake, Atsuji Okano, Kazuhiko Hoji, Tosaku Miki, Akio Sakashi ...
1959 Volume 7 Issue 5 Pages
634-640
Published: July 20, 1959
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Deacetylation with snail enzyme was carried out on 16-acetyl-and 16-propionyldigitalinum verum monoacetates and the corresponding 16-acetyl-and 16-propionyldigitalinum verum were obtained. Characteristics of these compounds were examined and it was found that the toxicity of 16-acetyldigitalinum verum was far higher than that of the original monoacetate.
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Tetsuji Kametani, Keiichiro Fukumoto, Yukio Nomura
1959 Volume 7 Issue 5 Pages
641-644
Published: July 20, 1959
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Treatment of 4-benzylvanillic acid with thionyl chloride, without use of a catalyst, afforded a polymer and sublimation of this polymer in vacuo gave a dimer of vanillide. According to the molecular weight determination and infrared absorption spectra, this polymer was recognized to be a tetramer and to have an ester, so that the polymer must have been formed from four molecules of the acid by removal of benzyl chloride during the reaction. Therefore, it is thought to be a polyester. The sublimate on the other hand was found to be a dimer formed from the tetramer by thermal decomposition.
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Risaburo Nakai, Michiyasu Sugii, Chiaki Tanaka
1959 Volume 7 Issue 5 Pages
645-646
Published: July 20, 1959
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The reaction between phenylacetic acid and acetic anhydride in the presence of pyridine was studied by using carboxyl-labeled (with
14C) phenylacetic acid. It was found that the carbon dioxide was liberated from the carboxyl group of phenylacetic acid.
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Yuichi Kanaoka
1959 Volume 7 Issue 5 Pages
647
Published: July 20, 1959
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Yuichi Kanaoka, Masanao Terashima, Tetsuo Kimura
1959 Volume 7 Issue 5 Pages
648-649
Published: July 20, 1959
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Shoshichiro Kimoto, Masao Okamoto, Hiroshi Kondo
1959 Volume 7 Issue 5 Pages
650-651
Published: July 20, 1959
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Hisao Tsukamoto, Satoshi Toki, Kyokuritsu Kaneda
1959 Volume 7 Issue 5 Pages
651-654
Published: July 20, 1959
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In order to elucidate the transformation processes of MHB metabolites, 3-keto-MHB, α-3-OH-MHB, and β-3-OH-MHB were administered to rabbits. 3-Keto-nor-MHB, 3-keto-MHB, and 3-OH-MHB have been identified in every case from the 24-hour urine by buffered-paper chromatography. From these and the results of quantitative studies, it is concluded that the 3-ketone and 3-hydroxyl groups in the cyclohexenyl ring are interconvertible and the equilibrium is in favor of 3-OH-MHB.
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Tyunosin Ukita, Kinzo Nagasawa
1959 Volume 7 Issue 5 Pages
655-657
Published: July 20, 1959
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