Reaction of Heteroaromatic Analogs of Homophthalic Anhydride : Synthesis of Hetero Analogs of peri-Hydroxy Polycyclic Aromatic Compounds, Isocoumarins, Isoquinolinones, and Related Compounds

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概要

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• The reactions of heterohomophthalic anhydrides, 3-carboxy-1-methylindole-2-acetic anhydride (4), 2-carboxybenzo [b] furan-3-acetic anhydride (5), 2-carboxythiophene-3-acetic anhydride (6), and 3-carboxy-1,4-dimethylpyrrole-2-acetic anhydride (23) with carbon-carbon multiple bonds (C=C and C≡C), acylating agents, and cyclic imines are described. Treatment of the anhydrides (4-6) with various compounds containing carbon-carbon multiple bonds (7-10) in the presence of a strong base caused cycloaddition with spontaneous extrusion of carbon dioxide to give the corresponding linearly condensed peri-hydroxy heteroaromatic compounds (11-19), regioselectively. Base-catalyzed acylation of 4 with acetic anhydride and β, β-dimethylacryloyl chloride gave 3,5-dimethylpyrano [4,3-b] indol-1 (5H)-one (21) and 3,3,11-trimethyl-3,4-dihydropyrano [4', 3' : 2,3]-pyrano [4,5-b] indole-1,6 (11H)-dione (22), respectively. Reaction of the anhydrides (4,6,and 23) with 3,4-dihydroisoquinoline (24) gave the corresponding condensation products, 14-carboxy-13-methyl-5,6,14,14a-tetrahydrobenz [a] indolo [3,2-g] quinolizin-8 (13H)-one (25), 12-carboxy-5,6,12,-12a-tetrahydrobenzo [a] thieno [2,3-g] quinolizin-8-one (26) and 12-carboxy-11-methyl-5,6,12,12a-tetrahydrobenzo [a] pyrrolo [3,2-g] quinolizin-8 (11H)-one (27), in high yields.

• 公益社団法人日本薬学会の論文
• 1985-11-25

著者

• 田村 恭光

  Faculty Of Pharmaceutical Sciences Osaka University

• 北 泰行

  大阪大学大学院薬学研究科

• Kita Yasuyuki

  Graduate School Of Pharmaceutical Sciences Osaka University Yamadaoka

• 毛利 慎一郎

  Faculty of Pharmaceutical Sciences, Osaka University

• 前田 初男

  Faculty of Pharmaceutical Sciences, Osaka University

• 前田 初男

  Faculty Of Pharmaceutical Sciences Osaka University

• 毛利 慎一郎

  Faculty Of Pharmaceutical Sciences Osaka University

• 北 泰行

  Faculty Of Pharmaceutical Sciences Osaka University

• 津越 光喜

  Faculty of Pharmaceutical Sciences, Osaka University

• 津越 光喜

  Faculty Of Pharmaceutical Sciences Osaka University

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