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Masaichiro Masui, Hiroteru Sayo, Keiichi Kishi
1964 Volume 12 Issue 12 Pages
1397-1405
Published: December 25, 1964
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Polarographic reduction mechanism of aliphatic ethyl nitrocarboxylates was investigated. The decrease of the wave height in alkaline region was ascribed to the conversion of the nitro form to aci-nitro anion rather than the ester hydrolysis. Only ethyl nitroacetate developed a wave for the aci-nitro anion. The coulometric n values and the products obtained, combined with the polarographic results, suggest the scheme (1) as the most probable reduction mechanism. The production of amine is only possible through C=N double bond formation, but not through hydroxyamino derivatives as usually suggested.
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Zen-ichi Horii, Chuzo Iwata, Ichiya Ninomiya, Nobuhiko Imamura, Masayo ...
1964 Volume 12 Issue 12 Pages
1405-1415
Published: December 25, 1964
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The previous work on the condensation of the several cyclic ketones and the 3-methylaminopropionates [This Bulletin, 10, 940(1962)] was re-investigated. As a result, it was shown that the condensation of cyclohexanone and ethyl 3-methylaminopropionategave 1-methyl-2, 3, 5, 6, 7, 8-hexahydro-4(1H)-quinolone (III) accompanied with a small amount of 1-methyl-3, 4, 5, 6, 7, 8-hexahydro-2(1H)-quinolone(IV), while the same condensation of 2-tetralone and methyl 2-methyl-3-methylaminopropionate gave 2, 4-dimethyl-1, 2, 5, 6-tetrahydrobenzo [f] quinolin-3(4H)-one (VIII) as a major product, and 2, 4-dimethyl-3, 4, 5, 6-tetrahydrobenzo [f] quinolin-1(2H)-one (IX) and 1, 3-dimethyl-1, 2, 5, 10-tetrahydrobenzo [g]-quinolin-4 (3H)-one (X) as minor products. Unequivocal synthetic proofs were given to these reaction products. The results enabled us to develop some discussion on the course of this type of the reaction. Revisions on the structures of the products in the previous paper were also described.
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Tsutomu Momose, Yo Ueda, Mitsuyoshi Kageura, Toshiko Masumura, Kiyoko ...
1964 Volume 12 Issue 12 Pages
1415-1418
Published: December 25, 1964
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3, 3'-Bi [cholesta-2, 4-diene], an oily mixture, cholesta-3, 5-diene, cholesteryl chloride, and cholesteryl acetate were isolated from the reaction mixture of cholesterol with perchloric acid, phosphoric acid, and ferric chloride. The first three substances were shown to be responsible for the coloration. Ferric chloride played a considerably important role in the coloration.
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Akira Takamizawa, Kentaro Hirai
1964 Volume 12 Issue 12 Pages
1418-1424
Published: December 25, 1964
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The acid catalyzed condensation reactions of N-substituted ureas with enolether ester (I) or nitrile (II) were carried out, and the condensation products were isolated and those structures were confirmed. Alkylation of ethyl 2-oxo-1, 2, 3, 4-tetrahydro-5-pyrimidinecarboxylate (XXI) afforded N-substituted tetrahydropyrimidines. Dehydrogenation of these N-substituted tetrahydropyrimidines gave N-substituted dihydropyrimidines readily.
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Yasuo Makisumi
1964 Volume 12 Issue 12 Pages
1424-1432
Published: December 25, 1964
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Thermal rearrangement of allyl 4-quinolyl ethers in 1-methylnaphthalene of without solvent resulted in the formation of good yields of the ortho-Claisen rearrangement products and small amounts of the lactim ehter-lactam isomerization products (1-allyl-4 (1H)-quinolones). A part of the Claisen rearrangement products were consecutively transformed into the 2, 3-dihydrofuro [3, 2-c] quinoline derivatives by their intramolecular cyclization in the process of this reaction. It was confirmed that the latter isomerization reaction is an intermolecular rearrangement.
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Ken'ichi Takeda, Taichiro Komeno, Shoichi Ishihara
1964 Volume 12 Issue 12 Pages
1433-1439
Published: December 25, 1964
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By treatment of potassium thiolacetate 6β-bromo-4-en-3-one steroids were converted to 6α-acetylthio-4-en-3-ones, which were further converted to 5'-methylthieno [4', 3', 2'-4, 5, 6]-5-en-3-ones by heating with sodium hydride in toluene
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Kazuo Tori
1964 Volume 12 Issue 12 Pages
1439-1446
Published: December 25, 1964
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Full interpretation of the proton magnetic resonance spectra of α-and β-thujones by using the solvent effect revealed that they take a boat-like envelope conformation. This conclusion was also supported by ultraviolet spectroscopy.
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Issei Iwai, Tadahiro Iwashige, Yasuo Yura, Norio Nakamura, Kiyoshi Shi ...
1964 Volume 12 Issue 12 Pages
1446-1451
Published: December 25, 1964
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The addition of cyanogen bromide to an acetylenic bond was studied. Phenylacetylene reacted with cyanogen bromide in the presence of aluminum bromide to afford trans-β-bromocinnamonitrile. Similarly, p-bromo-and p-methoxyphenylacetylene, tolane and methylphenylacetylene yielded corresponding β-bromocinnamonitriles. Nevertheless, p-nitrophenylacetylene did not react with cyanogen bromide under the same conditions.
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Tadakazu Tsuji, Junzo Kawabata, Sachiko Kobayashi, Takeo Ueda
1964 Volume 12 Issue 12 Pages
1451-1457
Published: December 25, 1964
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Seven series of compounds, i.e. p-alkylbezenesulfonamide, N-alkyl and N-(4-alkyl-phenyl) derivatives of p-toluenesulfonamide, p-alkoxybenzenesulfonamide, N-phenyl-p-alkoxybenzenesulfonamide, N-(4-alkoxyphenyl)-p-toluenesulfonamide and p-(p-alkylbenzenesulfonamido)-N-alkylbenzamide, were synthesized and examined as to their antiviral activities on viruses of Japanese encephalitis, influenza A and poliomyelitis. Several compounds were found effective for the in vitro test on Lansing strain of poliomyelitis virus. Among these effective compounds, N-phenyl-p-toluenesulfonamide was found to possess the promising in vivo activity on Lansing strain virus.
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Akira Tahara, Ken-ichi Hirao, Yasuhiko Hamazaki
1964 Volume 12 Issue 12 Pages
1458-1464
Published: December 25, 1964
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Catalytic hydrogenation of methyl 9-oxo-10-hydroxypodocarpa-5, 7, 10, 13-tetraen-16-oic acid enantiomer (V) and methyl 7-nitro-9-oxo-10-hydroxypodocarpa-5, 7, 10, 13-tetraen-16-oate enantiomer (IV), 9-oxo-10-hydroxypodocarpa-5, 7, 10, 13-tetraen-16-oate enantiomer (VI) in absence of sulfuric acid gave the respective 9α, 10α-dihydroxy compounds (IX), (X), and (XI), which are in contrast with the catalytic hydrogenation of methyl 9-oxo-10-acetoxypodocarpa-5, 7, 10, 13-tetraen-16-oate enantiomer (III) and (IV) in presence of sulfuric acid.
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Hisashi Nogami, Manabu Hanano, Jun Watanabe
1964 Volume 12 Issue 12 Pages
1465-1471
Published: December 25, 1964
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1.The penetration of water and solutes though the intestinal barrier in vitro was investigated with the technique described by Smyth & Taylor. Sulfisomezole concentration in the fluid transported to the serosal surface was higher than that in the mucosal solution. This phenomenon was not observed with sulfathiazole or sulfaguanidine. 2. The uphill transport of sulfisomezole was demonstrated with the technique of Wilson & Wiseman employing everted sacs. 3. In experiments with the technique of Smyth & Taylor the level of sulfathiazole or sulfaguanidine concentration in the transported fluid was maintained approximately constant through the changes of the transport rate of fluid. On the other hand the increase of sulfisomezole concentration in the transported fluid corresponded to the increase of the transport rate of fluid, although the relationship between them was not linear. 4. No particular correlation was observed between the penetration of sulfisomezole and that of sodium ion. 5. It was suggested that the uphill transport of sulfisomezole was explainable from the view-point of pH-partition hypothesis and that 2, 4-dinitrophenol might decrease the penetration of sulfisomezole after disturbing the mechanism of physiological pH maintenance at the absorptive surface.
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Takuzo Nishimura, Bunji Shimizu, Issei Iwai
1964 Volume 12 Issue 12 Pages
1471-1478
Published: December 25, 1964
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A new synthetic method of pyrimidine and purine ribosides was introduced. Condensation of tribenzoylribofuranosyl chloride with trimethylsilyl derivatives of pyrimidines and purines and then deacylation furnished natural ribose nucleosides in good yields. In the syntheses of uridine and ribofuranosylthymine, α-isomers were also isolated and the determinations of the structures were described.
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Naoto Yoneda
1964 Volume 12 Issue 12 Pages
1478-1492
Published: December 25, 1964
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A synthesis of9, 10-dimethoxy-1, 2, 3, 4, 6, 7-hexahydro-2, 6-methano-11bH-benzo [a]-quinolizine having a new ring system was described. Thus, dl-N-benzyl-3-(3, 4-dimethoxyphenyl) alanine ester (VI) was condensed with succinic anhydride followed by esterification to give amido-ester (IX), which on being cyclized with phosphoryl chloride under reflux furnished the corresponding dihydroisoquinoline derivative (X) isolated as iodide. When the latter was reduced with sodium borohydride-methanol, there were obtained α-and β-isomers of tetrahydroisoquinoline derivative (XI)ca. in a ratio 5 : 1. On being cyclized with sodium hydride-toluene they gave one and the same cyclic β-ketoester (XII), which was condensed with ethyl bromoacetate followed by ketone fission to yieldγ-ketoester (XV). An alternative route XV was also discribed. XV was then reduced with sodium borohydride and the resultant alcohol (XVIII) was chlorinated to give the chloride (XIX), which was reduced with lithium aluminum hydride-tetrahydrofuran. The reduction product was directly tosylated and worked up properly furnishing the cyclized product, which was characterized as perchlorate. On being reduced catalytically the latter furnished the ultimate product (I). A smaller quantity of by-product was also obtained in the final cyclization step, to which structure (I-B) was postulated.
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Zen-ichi Horii, Chuzo Iwata, Yasumitsu Tamura
1964 Volume 12 Issue 12 Pages
1493-1495
Published: December 25, 1964
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trans-4-Methyl-1, 2, 3, 4, 4a, 5, 6, 10b-octahydrobenzo [f] quinoline (III) was prepared by Birch reduction of 4-methyl-1, 2, 3, 4, 5, 6-hexahydrobenzo [f] quinoline (I) and by Clemmensen reduction of trans-4-methyl-3, 4, 4a, 5, 6, 10b-hexahydrobenzo [f] quinolin-1(2H)-one (V). The cis isomer (II) of III was prepared by lithium aluminum hydride reduction of cis -4-methyl-1, 2, 4a, 5, 6, 10b-hexahydrobenzo [f] quinolin 3-(4H)-one (IV).
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Eiji Ochiai, Hiroshi Mitarashi
1964 Volume 12 Issue 12 Pages
1495-1497
Published: December 25, 1964
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2-Ethyleneiminomethyl-4-nitroquinoline-N-oxide was prepared by the reaction of 2-chloromethylquinoline-N-oxide with potassium nitrate and sulfuric acid, followed by treatment with ethyleneimine. Nitration of 2-ethyleneiminomethylquinoline-N-oxide with potassium nitrate and sulfuric acid to 2-ethyleneiminomethyl-4-nitroquinoline-N-oxide was failed.
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Masuko Akagawa, Mitsuo Sasamoto, Masayuki Onda
1964 Volume 12 Issue 12 Pages
1497-1499
Published: December 25, 1964
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The morphinan derivatives (II and III) were examined by means of thin-layer chromatography, gas chromatography and nuclear magnetic resonance spectroscopy. Their purities were certainly confirmed by gas chromatography and nuclear magnetic resonance spectroscopy, but thin-layer chromatography was not suitable for this purpose.
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Tsutomu Momose, Yo Ueda, Mitsuyoshi Kageura, Toshiko Masumura, Kiyoko ...
1964 Volume 12 Issue 12 Pages
1500-1502
Published: December 25, 1964
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3, 3'-Bi[cholesta-2, 4-diene] was isolated from the color reaction mixture of cholesterol in Zak-Henly's method. Its chloroform solution develops a purple red and a pink color with the Zak-Henly's reagent and a mixture of acetic acid and conc. Sulfuric aicd, respectively.
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Tyunosin Ukita, Yasushi Takeda, Hikoya Hayatsu
1964 Volume 12 Issue 12 Pages
1503-1509
Published: December 25, 1964
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Uridylyl-(3'→5')-uridine (UpU) was synthesized via two different routes, i.e. by condensation of 2', 5'-di-O-trityluridine (I) with 2', 3'-di-O-acetyluridine 5'-phosphate (IV) (Route A) and by condensation of 2', 3'-di-O-acetyluridine (VI) with 2', 5'-di-O-trityluridine 3'-phosphate (II) (Route B). The acid treatments to remove trityl groups were performed with 80% acetic acid at both 37° and 100° in several time intervals. The yields of the final product, UpU, and the amounts of uridylyl-(2'→5')-uridine contained in the UpU were compared.
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Michihiko Ochiai, Toshiya Kamikado
1964 Volume 12 Issue 12 Pages
1515-1520
Published: December 25, 1964
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Seiichi Saito, Tadasu Tanaka, Keishi Kotera, Hideo Nakai, Norio Sugimo ...
1964 Volume 12 Issue 12 Pages
1520-1523
Published: December 25, 1964
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Hiroshi Mitsuhashi, Taro Nomura
1964 Volume 12 Issue 12 Pages
1523-1525
Published: December 25, 1964
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Shun-ichi Yamada, Kazuo Achiwa
1964 Volume 12 Issue 12 Pages
1525-1529
Published: December 25, 1964
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Shigekatsu Nakajima, Ken'ichi Takeda
1964 Volume 12 Issue 12 Pages
1530
Published: December 25, 1964
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Shoji Hara
1964 Volume 12 Issue 12 Pages
1531
Published: December 25, 1964
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