Studies on Ketene and Its Derivatives. CXVI. Some Reactions of 3-Oxocyclobuta[c]quinoline-2-spiro-2'-oxetane : [4+2]Cycloaddition via ortho-Azaquinodimethane

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概要

• 論文の詳細を見る

• 2-Methylenehexahydrocyclobuta[c]quinoline 2 obtained from cyclobuta[c]quinolinespiro-oxetanone 1 was isomerized to 2-methyltetrahydrocyclobuta[c]quinoline 5 by treatment with sodium ethoxide in dry toluene. The reaction of compound 5 with olefins, such as methyl acrylate, acrylonitrile, N-phenylmaleimide, and methyl methacrylate under reflux in dry xylene gave [4+2] cycloadducts, hexahydrophenanthridine derivatives 6-9. Ethoxycarbonylmethyl-cyclobuta[c]quinolines 4 generated by ethanolysis of 1 were treated with thionyl chloride in pyridine to give dehydrated products, (E)-2-(ethoxycarbonylmethylene)cyclobuta[c]quino-line (E)-13 and its isomer (Z)-13. Compounds (E)-13 and (Z)-13 isomerized to the same product, 2-(ethoxycarbonylmethyl)cyclobuta[c]quinoline 14 in the presence of sodium ethoxide in dry benzene at room temperature. Similarly, compound 14 reacted with olefins to give hexahydrophenanthridine derivatives 15-18 via a 2-oxoquinoline-3,4-diquinomethane intermediate.

• 社団法人日本薬学会の論文
• 1983-08-25

著者

• 千葉 卓男

  Pharmaceutical Institute, Tohoku University

• 加藤 鐵三

  東北大学薬学部

• 千葉 卓男

  Pharmaceutical Institute Tohoku University

• 加藤 鐵三

  Pharmaceutical Institute. Tohoku University

• 岡田 稔

  Third Institute of New Drug Research Otsuka Pharmaceutical Co., Ltd.,

• 岡田 稔

  Pharmaceutical Institute, Tohoku University

• 岡田 稔

  Third Institute Of New Drug Research Otsuka Pharmaceutical Co. Ltd.

• Okada Minoru

  Third Institute Of New Drug Research Otsuka Pharmaceutical Co. Ltd.

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