Studies on Tertiary Amine Oxides. XLVIII. The Reaction of Quinoline N-Oxide with Acrylonitrile

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概要

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• Treatment of quinoline N-oxide (I) with acrylonitrile and acetic anhydride in hot dioxane or dimethylformamide resulted in the formation of β-(2-quinolyl) acrylonitrile (II) and di-(2-quinolyl) acetonitrile (III) in 34.4 and 3.3% yields, respectively. No definite product was obtained in the absence of acetic anhydride, whereas the reaction in excess acetic anhydride using no solvent caused the increase of the formation of III and conversely the decrease of that of II. In spite of such a markedly important role of acetic anhydride, it was further disclosed that, when a dioxane solution of I and acrylonitrile was heated in the presence of a catalytic amount of hydroquinone, II and β-(2-quinolyl)-lactonitrile (XI) were produced. The acrylonitrile derivative II should be assumed to result from the 1,3-dipolar cycloaddition between the free I and acrylonitrile. The mechanism of formation of III was also discussed. Acrylamide and ethyl acrylate showed similar behaviors to that of acrylonitrile.

• 公益社団法人日本薬学会の論文
• 1974-08-25

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

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• 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
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• 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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