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Takanobu Itai, Shozo Kamiya
1961 Volume 9 Issue 2 Pages
87-91
Published: February 25, 1961
Released on J-STAGE: March 31, 2008
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4-Azidoquinoline (VII) and its N-oxide (IV) were prepared from the corresponding hydrazino compounds (VI and III) with sodium nitrite and also from chloro compounds (II) with sodium azide. Similarly, 4-azidopyridine 1-oxide and 4-azido-2-picoline were obtained. The addition reaction of their azido group to propargyl alcohol, photolysis, and thermal decomposition were examined.
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Eiji Ochiai, Hitoshi Minato
1961 Volume 9 Issue 2 Pages
92-96
Published: February 25, 1961
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Diazotization of decarbonylmethylmatrinamine (I) with silver nitrite in 10% hydrobromic acid yielded decarbonylmethylmatrinol (II) and the quaternary salt (III). Tosylation of matrinol (XIII) gave matridine (VIII), and reaction of (XIII) with trityl chloride gave matrine (XIV) quantitatively. The facile ring-closure of these compounds may be explained by the fact that the terminal end of the side chain is sterically very close to the nitrogen atom in ring-C.
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Hitoshi Minato, Kenichi Takeda
1961 Volume 9 Issue 2 Pages
97-104
Published: February 25, 1961
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The steric effect of matridine (I) on von Braun degradation was investigated. It was concluded that the structure of the degradation product, monobromomatridine monocyanamide (IV), was represented by formula (IVa) and its dehydrogenated product with mercuric acetate, enamine (VI) by formula (VIa).
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Yoji Arata, Shigehiko Sugasawa
1961 Volume 9 Issue 2 Pages
104-107
Published: February 25, 1961
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When treated with phosphoryl chloride in boiling toluene 2-veratrylcyclopentanone oxime suffered an intramolecular dehydration, in which oxime-OH took part, to form 6, 7-dimeth-oxy-2, 3, 9, 9a-tetrahydro-1H-cyclopenta [b] quinoline. Spontaneous dehydrogenation of the latter resulted in the formation of 6, 7-dimethoxy-2, 3-dihydro-1H-cyclopenta [b] quinoline as the ultimate product. 2-Veratrylcyclohexanone oxime behaved similarly, but gave an inferior yield of 6, 7-dimethoxy-1, 2, 3, 4-tetrahydroacridine. Both products were identified with the authentic specimens. This is a novel dehydration reaction of an oxime.
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Ko Kaneko
1961 Volume 9 Issue 2 Pages
108-109
Published: February 25, 1961
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The radioactivity of p-hydroxycinnamic acid [carbonyl-
14C] fed to the plant was found in the methyl-carbon of the side chain of anethole produced by Foeniculum vulgare M.
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Hisashi Tanaka, Akira Yokoyama
1961 Volume 9 Issue 2 Pages
110-114
Published: February 25, 1961
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β-Mercapto-p-chlorohydrocinnamic acid, β-mercapto-p-methoxyhydrocinnamic acid, β-mercapto-β-(1-naphthyl) propionic acid, and β-mercapto-β-(2-furyl) propionic acid and their alkyl esters were prepared. These β-mercapto-acid esters formed stable chelates with copper and nickel. The ratio of ligand to the metal was 1 : 1 in copper chelates and 2 : 1 in nickel chelates. The reaction with nickel was particularly sensitive.
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Hiroshi Mitsuhashi, Ukon Nagai, Toshio Muramatsu
1961 Volume 9 Issue 2 Pages
115-119
Published: February 25, 1961
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The structure of ligustilide was discussed upon the fact that sedanonic acid, 3-butyl-phthalide, and 2-valerylcyclohexanecarboxylic acid were obtained by catalytic hydrogenation. Tentative structures were proposed on the basis of available data. The position of double bonds, however, remains to be determined.
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Shunichi Yamada, Kazuo Achiwa
1961 Volume 9 Issue 2 Pages
119-123
Published: February 25, 1961
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A new thiamine analog, 3- (2, 4-dioxo-1, 2, 3, 4-tetrahydro-5-pyrimidinyl) methyl-4-methyl-5- (2-hydroxyethyl) thiazolium nitrate (II) was synthesized from 5-cyanouracil (III). In the course of the reduction of (III), thymine was obtained besides the amine (IV). Further, a new method for obtaining (IV) was found.
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Seigo Fukushima
1961 Volume 9 Issue 2 Pages
124-126
Published: February 25, 1961
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The mechanism of novel cyclization of 1-Methoxy-2-acetyl-1, 3-diacetoxynaphthalene (IV) to 2-methyl-5, 6-dihydroxy-7, 8-benzochromone (V) was investigated with
14C-tracer method and it was found that about 90% of the reaction followed the route of (IV)→(IV')→(V).
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Seigo Fukushima
1961 Volume 9 Issue 2 Pages
127-130
Published: February 25, 1961
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The mechanism of novel cyclization of 1, 3, 4-triacetoxy-2-acetylnaphthalene (I) to 2-methyl-3-acetyl-5-hydroxy-6-acetoxy-7, 8-benzochromone (II) was investigated by the
14Ctracer method and it was found that about 70∼80% of the reaction followed the route of (I)→(I')→(II).
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Kyosuke Tsuda, Eiji Ohki, Junnosuke Suzuki, Hiroshi Shimizu
1961 Volume 9 Issue 2 Pages
131-138
Published: February 25, 1961
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It was observed that the methyl group in the 19-position of 3β-acetoxylanosta-5, 8-dien-7-one (I) would be easily eliminated as methane and the B-ring was aromatized by treatment with zinc. The other chemical and photochemical behaviors of (I) were examined.
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Tetsuji Kametani, Yukio Nomura
1961 Volume 9 Issue 2 Pages
139-145
Published: February 25, 1961
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2-Methyl-3-ethoxycarbonyl-9, 10-dimethoxy-1, 2, 3, 4, 6, 7-hexahydro-11bH-benzo [a] quinolizinium salt was prepared by cyclization of the piperidone compound synthesized by the condensation of 3, 4-dimethoxyphenethyl bromide and 4-methyl-5-ethoxycarbonyl-2-piperidone in the presence of sodium hydride. Its amino derivative was prepared by the Curtius degradation, via the hydrazide, azide, and benzylurethan. The amino compound was diazotized with sodium nitrite in acetic acid and converted to the hydroxyl derivative, which was purified as its methiodide. In order to prove the presence of this hydroxyl group, the compound was led to its methanesulfonate. The hydroxy base was methylated with diazomethane, in the presence of fluoroboric acid in chloroform, and the objective methyl ether, i.e. rac-tetrahydrorotundine, was obtained as its methiodide. Some discussions were made on the reaction of aliphatic primary amines with nitrous acid.
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Toshiro Murata
1961 Volume 9 Issue 2 Pages
146-148
Published: February 25, 1961
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Marked increase of urinary glucuronic acid was observed in rabbits administered with ECC. A glucuronide of the metabolite of ECC was separated from urine of man who received ECC orally and it was identified as the glucuronide of OH-ECC by the reaction of β-glucuronidase and subsequent paper chromatography.
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Takanobu Itai, Shigeru Sako
1961 Volume 9 Issue 2 Pages
149-151
Published: February 25, 1961
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Makoto Shirasaka
1961 Volume 9 Issue 2 Pages
152-155
Published: February 25, 1961
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[in Japanese]
1961 Volume 9 Issue 2 Pages
156-158
Published: February 25, 1961
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Application of Botrytis cinerea to 17α-hydroxyprogesterone, deoxycorticosterone, Reichstein's compound S, and corticosterone, as the substrate steroids, resulted in the formation of 6β-hydroxy derivative alone from 17α-hydroxyprogesterone and the compound S, 15β-hydroxy derivative alone from corticosterone, and both derivatives from deoxycorticosterone. These results indicated that this fungus possessed a marked substrate specificity. This fungus was also found to dehydrogenate the 11β-hydroxy group in corticosterone.
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Makoto Shirasaka, Masako Tsuruta
1961 Volume 9 Issue 2 Pages
159-163
Published: February 25, 1961
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11α-Hydroxy derivatives of progesterone, 17α-hydroxyprogesterone, deoxycorticosterone, and Reichstein's compound S were obtained solely by the use of Gloeosporium kaki and Glomerella lagenarium. These fungi did not affect corticosterone.
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Harutada Negoro, Hiroo Takada, Shogo Ueda, Toshihiko Hoshi
1961 Volume 9 Issue 2 Pages
164-166
Published: February 25, 1961
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Molecular complex formation between pyrazine-or pyridine-monocarboxamides and sodium p-aminosalicylate or sodium salicylate in aqueous solution was studied by measuring the heats of solution values. Assuming 1 : 1 complex formation, the equilibrium constant (K) and the heat of formation (ε) were calculated. Comparing these values for pyrazinamide with corresponding values obtained spectrophotometrically and reported in the preceding paper, and taking the experimental errors and the difference in temperature at which experiments were made into account, they may be judged to coincide with each other.
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Toshiro Murata
1961 Volume 9 Issue 2 Pages
167-168
Published: February 25, 1961
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One of metabolites of ECC in human urine was assumed to be 1-ethynylcyclohexane-1, 2-diol from its color reaction. For confirmation, 1-ethynylcyclohexane-trans-1, 2-diol and its isomer were synthesized from ECC and the two products prepared were confirmed as the same 1, 2-diols by catalytical reduction.
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Toshiro Murata
1961 Volume 9 Issue 2 Pages
169
Published: February 25, 1961
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Hiroshi Mitsuhashi, Tsuneo Itoh
1961 Volume 9 Issue 2 Pages
170
Published: February 25, 1961
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Masaiti Yasue, Yosisige Kato, Toshihiko Kishida, Hideo Ota
1961 Volume 9 Issue 2 Pages
171
Published: February 25, 1961
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