Studies on Tertiary Amine Oxides. LI. Reactions of Quinoline and Isoquinoline N-Oxides with Propiolates and Methacrylonitrile

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概要

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• The 1,3-dipolar cycloaddition between quinoline N-oxide (I) and methyl propiolate progressed in the presence of acetic anhydride or hydroquinone to afford methyl α-formyl-2-quinolineacetate (IIa). The reaction with ethyl propiolate in the presence of hydroquinone gave the corresponding ethyl ester (IIb). The reaction of I with methacrylonitrile in the presence of hydroquinone produced cyanohydrin of 2-acetonylquinoline (VIII) or 2-acetonylquinoline (IX) and 2-cyanoquinoline (X). Isoquinoline N-oxide (XI) was less reactive and resisted the reaction with propiolates, but reacted with methacrylonitrile in the presence of hydroquinone to give 1-acetonyl-isoquinoline (XII), 1-cyanoisoquinoline (XIII) and isoquinoline.

• 公益社団法人日本薬学会の論文
• 1975-02-25

著者

• 口野 嘉幸

  Faculty Of Pharmaceutical Sciences Kyushu University:(present Address)biology Division National Canc

• 舟越 和久

  Faculty of Pharmaceutical Sciences, Kyushu University

• 舟越 和久

  Faculty Of Pharmaceutical Sciences Kyushu University

• 執行 洋陸

  Tokyo Research Laboratories, Kowa Co., Ltd.,

• 執行 洋陸

  Tokyo Research Laboratories Kowa Co. Ltd.

関連論文

• Insight into the Cyclization of 6-Octen-1-als with Rhodium(I) Complex
• Diastereoselective Cyclization of 6-Octen-1-als with Rhodium(I)-Complex
• Studies on Tertiary Amine Oxides. LVII. Re-examination of the Reaction of Quinoline 1-Oxide with Acetic Anhydride, and the Related Reactions
• Studies on Tertiary Amine Oxides. LI. Reactions of Quinoline and Isoquinoline N-Oxides with Propiolates and Methacrylonitrile
• Studies on Tertiary Amine Oxides. XLVIII. The Reaction of Quinoline N-Oxide with Acrylonitrile
• Studies on Tertiary Amine Oxides LXXXII. : The Reaction of 1-Oxido-4(or 2)-pyridinediazonium Tetrafluoroborate with Olefins in the Presence of Palladium Complex
• Studies on Tertiary Amine Oxides. LXII. A Novel Formation of Quinolinium Methylides by the Reaction of Quinoline 1-Oxides with Active Methylene Compounds in the Presence of an Acylating Agent
• Synthesis and Antiarrhythmic Activity of Disubstituted Phenylpyridine Derivative
• Simple Synthesis of trans-3,4-Bis(methoxycarbonylmethyl)cyclopentanone
• Reaction of Tryptamine and Aniline with δ-Valerolactone and Its Dehydro Derivatives. A New Synthesis of 1,2,3,4,6,7,12,12b-Octahydroindolo [2,3-α] quinolizine
• Studies on Tertiary Amine Oxides. LXXXI. Formation of 1-lsoquinoliniomethylides by the reaction of Isoquinoline 2-Oxide with Cyanoacetic Acid and Benzoylacetonitrile in the Presence of Acetic Anhydride
• Studies on Tertiary Amine Oxides. LXXX. Reaction of Quinoline 1-Oxide with Phenylacetic Anhydride
• SYNTHESIS BY MICROBIAL REDUCTION OF (S)-13-HYDROXY-9Z, 11E-OCTADECADIENOIC ACID, A DEFENSIVE SUBSTANCE IN RICE

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