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Satoshi Mizukami, Eizo Hirai
1966 Volume 14 Issue 12 Pages
1321-1332
Published: December 25, 1966
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The potentiometric titrations of 5-substituted-4-amino-2-methylpyrimidines were examined as a base in various nonaqueous solvents. The quantitative determinations were effectively carried out in acidic and dipolar aprotic solvents. The potentials at half neutralization point (HNP values) were used as a measure of the relative basicity of the pyrimidines in the solvents. The values in each of the solvents could be lineally correlated with the pKa (H
2O) values and the Hammett's σ
m for the 5-substituents. Some of the pyrimidines which deviated considerably from these linear relationships were discussed. Moreover, it was found that the differentiating titration of a mixture of pyrimidines might be facilitated with increasing of the reaction constant of the Hammett's equations. On the other hand, it was indicated by the Hammett's equations and by comparison of ultraviolet absorption spectra that these pyrimidines existed largely as the amino form in the solvents as well as in water and the actual proton acceptor in these molecules was the 1-position of pyrimidine ring.
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Yoshikazu Kondo, Kazue Kondo, Tsunematsu Takemoto, Tsuneo Ikenoue
1966 Volume 14 Issue 12 Pages
1332-1337
Published: December 25, 1966
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The relation between the chemical shifts (δ
0) of ortho-, meta-, and para-substituted benzoic acids at infinite dilution in pyridine and the Hammett σ values was investigated. A good linear correlation against σ constants was observed for any of ortho-, meta-, and para-substituted benzoic acids. No correlation has been found up to the present for ortho-substituted benzoic acids by direct method such as the one based upon physical chemistry or NMR, but a good linearity was obtained by the above method.
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Morio Ikehara, Fumio Harada, Eiko Ohtsuka
1966 Volume 14 Issue 12 Pages
1338-1346
Published: December 25, 1966
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Tubercidin (7-deazaadenosine) was converted to the 5'-O-monomethoxytrityl derivative, which was phosphorylated with P
1-diphenyl-P
2-morpholinopyrophosphorochloridate to afford the 2'-and 3'-monophosphates. The latter compound was acetylated to N, 2', 5'-tri-O-acetyltubercidin 3'-phosphate. N
6-Dimethyladenosine was converted to the 5'-benzoyl derivative which was phosphorylated with cyanoethyl phosphate and DCC to give the 2'-and 3'-monophosphates. N
6-Dimethyladenosine 3'-phosphate was protected by acetylation in the 2'-and 5'-positions. These protected 3'-phosphates were subjected to condensation with N, 2'-dibenzoyladenylyl-(3'→5')-N, 2', 3'-tribenzoyl-adenosine or N, 2'-dibenzoylcytidylyl-(3'→5')→N, 2', 3'-tribenzoylcytidine by the DCC procedure. The trinucleoside diphosphates 7-deazaadenylyl-(3'→5')-adenylyl-(3'→5')-adenosine, 7-deazaadenylyl-(3'→5')-cytidylyl-(3'→5')-cytidine, N
6-dimethyl-adenylyl-(3'→5')-adenylyl-(3'→5')-adenosine and N
6-dimethyladenylyl-(3'→5')-cytidylyl-(3'→5')-cytidine were purified by paper chromatography and paper electrophoresis. Complete digestion of these trinucleoside diphosphates with spleen phosphodiesterase established the 3'→5' phosphodiester linkages.
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Haruo Saikach, Masataka Ichikawa
1966 Volume 14 Issue 12 Pages
1347-1349
Published: December 25, 1966
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The condensations of (2-methyloxazolo) coumarin derivatives (I. II. and III) with 5-nitro-2-furaldehyde were proceeded by heating with fused zinc chloride. In this case, I was more readily condensed than II and III with aldehyde groups to give the corresponding condensation products.
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Haruo Saikachi, Masataka Ichikawa
1966 Volume 14 Issue 12 Pages
1350-1354
Published: December 25, 1966
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Ethyl (2-methyloxazolo) coumarin-3-carboxylates were hydrolyzed with 2% aq.sodium hydroxide solution to give the corresponding carboxylic acids, respectively. The acid chlorides prepared from the carboxylic acids were condensed with secondary amines to give the corresponding 3-carbamoyl derivatives in good yield, respectively. Diethylamine, pyrrolidine, piperidine, and morpholine were used as secondary amines.
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Torahiko Kishikawa, Tsuyoshi Yamazaki, Hidetaka Yuki
1966 Volume 14 Issue 12 Pages
1354-1360
Published: December 25, 1966
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_D-Glucuronic acid nucleotides of uracil (VI, VIII), thymine (XVIII), cytosine (VII), 5-bromo-and 5-iodo-uracil (IX, X) were prepared by Hilbert-Johnson and Fox's procedures for the syntheses of pyrimidine nucleosides. VI was also obtained from 1-deoxy-1-(2, 4-dioxo-1, 2, 3, 4-tetrahydro-1-pyrimidinyl)-β-
D-glucopyranose by O
2-oxidation in the presence of Pt-catalyst. The structure and properties of the nucleosides synthesized were bridefly discussed.
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Torahiko Kishikawa, Hidetaka Yuki
1966 Volume 14 Issue 12 Pages
1360-1364
Published: December 25, 1966
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Condensation of 4-ethylthio-5-nitro-6-chloropyrimidine with methyl 1-amino-1-deoxy-2, 3, 4-tri-O-acetyl-β-
D-glucopyranuronate was effectd to give methyl 1-deoxy-1-(4-ethylthio-5-nitro-6-pyrimidinylamino)-2, 3-4-tri-O-acetyl-
D-glucopyranuronate (VI). Hydrogenation of nitro group of VI in the presence of platinum-catalyst and subsequent ring closure of 4, 5-diamino-derivative (VII) with carbon disulfide were achieved. 6-Ethylthio group of X was replaced to 6-hydrazino group followed by treatment with Raney nickel to afford 1-deoxy-1-(6-amino-9-purinyl)-β-
D-glucopyranuronamide (XII). VII was reacted with sodium nitrite to give ν-triazolo derivative (XIII), 6-ethylthio group of which was readily aminated to yield 1-deoxy-1-(7-amino-3H-ν-triazolo [4, 5-d] pyrimidin-3-yl)-β-
D-glucopyranuronamide (XIV).
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Torahiko Kishikawa, Hidetaka Yuki
1966 Volume 14 Issue 12 Pages
1365-1370
Published: December 25, 1966
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1-Phenyl-5, 6-diaminouracil (IX) or-2-thiouracil (X) prepared from 1-phenyl-6-aminouracil (V) or 1-phenyl-6-amino-2-thiouracil (VI) in an usual way was fused with urea or thiourea to yield 3-phenyluric acid and 3-phenylthiouric acid derivatives (XII, XIII, XIV and XV), while it was reacted with formamide to afford 3-phenylxanthine derivatives (XX and XXI), and with nitrous acid to give triazolo-derivatives (XXIV and XXV). Acetylation of IX or X resulted in formation of the corresponding 5-acetyl derivatives (XXVII and XXVIII) which on heating at 230∼240° as the sodium salts were converted into 8-methylpurine derivatives (XXIX and XXX). Preliminary anti-cancer testing results of the purine derivatives synthesized were described.
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Keiji Yoshida, Tokuo Kubota
1966 Volume 14 Issue 12 Pages
1370-1377
Published: December 25, 1966
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Oxidation of 2, 17β-dihydroxyandrosta-1, 4-dien-3-one (IIa) with manganese dioxide in acetone resulted in the ring contraction giving 17β-hydroxy-A-norandrost-3(5)-ene-1, 2-dione (IIIa) whereas the reaction, in the presence of acid, afforded 1ξ, 17β-dihydroxy-2-oxaandrost-4-en-3-one (IV). Oxidation of 4, 17β-dihydroxyandrosta-1, 4-dien-3-one (VI), even in the absence of acid, resulted in the ring cleavage yielding 5ξ, 17β-dihydroxy-4-oxaandrost-1-en-3-one (VII). Possible mechanisms for their reactions were discussed.
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Kin-ichi Imai, Akira Nohara, Mikio Honjo
1966 Volume 14 Issue 12 Pages
1377-1381
Published: December 25, 1966
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Iodine has been found to be an excellent catalyst for the synthesis of nucleosides, i.e., the reaction of 1-O-acetyl-2, 3, 5-tri-O-benzoyl-β-
D-ribofuranose with various purines in the presence of iodine resulted in the formation of corresponding 9-β-
D-ribonucleosides, and/or their isomers in good yields.
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Shun-ichi Yamada, Shiro Ikegami
1966 Volume 14 Issue 12 Pages
1382-1388
Published: December 25, 1966
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The reduction of 3, 4-dihydroisoquinoline derivatives with diborane in tetrahydrofuran was carrid out, but the hydroboration to the carbon-nitrogen double bond did not occur and the isolated product was the fairly stable amine borane complex II which could be easily recrystallized from isopropanol. Also, the reductions of 1, 2-dimethyl-3, 4-dihydroisoquinolinium iodide with diborane and 3, 4-dihydroisoquinoline and its 1-methyl derivative with diisopinocampheylborane were carried out and the results were discussed.
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Shiro Ikegami, Shun-ichi Yamada
1966 Volume 14 Issue 12 Pages
1389-1399
Published: December 25, 1966
Released on J-STAGE: March 31, 2008
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The reduction of the various Schiff bases with diborane in tetrahydrofuran was smoothly proceeded, being followed by the simple treatment with alcohol, to give the corresponding amines. The relative reactivity of the Schiff bases toward diborane increased with an increasing order of their basicities determined by the infrared absorption spectral method.
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Zen-ichi Horii, Koichi Morikawa, Yasumitsu Tamura, Ichiya Ninomiya
1966 Volume 14 Issue 12 Pages
1399-1404
Published: December 25, 1966
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Condensation and cyclization of ethyl 2-piperidineacetate with cyclohexanone gave a vinylogous lactam, 1, 2, 3, 4, 4a, 5, 7, 8, 9, 10-decahydro-6H-benzo [c] quinolizin-6-one (VII). The same reaction with 2-tetralone gave four compounds, all having the vinylogous lactam grouping. The structures of these compounds were assigned by their infrared, ultraviolet and nuclear magnetic resonance spectra.
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Hiroshi Miura, Nobusuke Kawano, Jr. Anthony C.Waiss
1966 Volume 14 Issue 12 Pages
1404-1408
Published: December 25, 1966
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Cyptomerin A (II) and B (III) were isolated from the leaves of Cryptomerin japonica D.D
ON and their structures were established by the alkaline degradation of their ethyl ethers as the first examples of naturally occurring hinokiflavone methyl ethers.
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Tetsuji Kametani, Hiroshi Sugahara, Setzu Asagi
1966 Volume 14 Issue 12 Pages
1408-1413
Published: December 25, 1966
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Attempted deoximation of 2-nitro-1-indanone oxime (I) with formalin and hydrochloric acid in acetone gave unexpected compounds, namely, 2-hydroxymethyl-2-nitro-1-indanone oxime (IV), 2-hydroxymethyl-2-nitro-1-indanone (V), and 2-nitro-1-indanone (VI).
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Yutaka Kawazoe, Masako Ohnishi
1966 Volume 14 Issue 12 Pages
1413-1418
Published: December 25, 1966
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It was demonstrated that the quantitative analysis of various kinds of acive hydrogens was conveniently carried out by nuclear magnetic resonance technique. The exchange reactivities of α-hydrogens adjacent to carbonyl functions were compared with each other by this technique.
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Sadao Oida, Masaaki Kurabayashi, Eiji Ohki
1966 Volume 14 Issue 12 Pages
1418-1424
Published: December 25, 1966
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Either 3-methyl-9α-hydroxy-9β-phenyl-3-azabicyclo [3.3.1] nonane (Ia) or 9β-hydroxy epimer (IIa) was treated in boiling alcohol in the presence of an acid to yield 9β-alkoxy compound (IIb) as a major product. Ia or IIa was decomposed with propionic anhydride at 160∼170° into one and the same reaction product from which styrene derivatives (VI and VII) were isolated. These facts illustrated the tendency of the skeleton of 9-phenylazabicyclo [3.3.1] nonane to yield the carbonium ion (V).
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Tarozaemon Nishiwaki
1966 Volume 14 Issue 12 Pages
1425-1426
Published: December 25, 1966
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Tokuo Kubota, Keiji Yoshida, Fumihiko Watanabe
1966 Volume 14 Issue 12 Pages
1426-1430
Published: December 25, 1966
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Tatsuzo Fujii, Tomio Fujii
1966 Volume 14 Issue 12 Pages
1430-1432
Published: December 25, 1966
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Shigeru Takanashi, Tsutomu Kawaguchi, Minoru Kawada
1966 Volume 14 Issue 12 Pages
1433-1434
Published: December 25, 1966
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Ching-Tan Chen, Koji Nakanishi, Shinsaku Natori
1966 Volume 14 Issue 12 Pages
1434-1437
Published: December 25, 1966
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Hiroshi Hikino, Keitaro Aota, Yukio Maebayashi, Tsunematsu Takemoto
1966 Volume 14 Issue 12 Pages
1439-1441
Published: December 25, 1966
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Hiroshi Hikino, Norio Suzuki, Tsunematsu Takemoto
1966 Volume 14 Issue 12 Pages
1441-1443
Published: December 25, 1966
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Masaiti Yasue, Norihisa Kawamura
1966 Volume 14 Issue 12 Pages
1443-1444
Published: December 25, 1966
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Teruhiko Meshi, Yoshishige Sato
1966 Volume 14 Issue 12 Pages
1444-1448
Published: December 25, 1966
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Tadashi Sasaki, Katsumaro Minamoto
1966 Volume 14 Issue 12 Pages
1448-1450
Published: December 25, 1966
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Akira Takamizawa, Kentaro Hirai, Teruyuki Ishiba
1966 Volume 14 Issue 12 Pages
1450-1451
Published: December 25, 1966
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Tozo Fujii, Taisuke Itaya, Shun-ichi Yamada
1966 Volume 14 Issue 12 Pages
1452-1454
Published: December 25, 1966
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