Synthesis and Application of Imidazole Deribatives. Synthesis of Pyrrolo[1,2-a]benzimidazoles and Azepino[1,2-a]benzimidazoles

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概要

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• 4-Methyl-4H-pyrrolo[1,2-a]benzimidazol-2(1H)-one derivatives (11a-d) were synthesized by intramolecular acylation of 1-carboxymethyl-2,3-dimethylbenzimidazolium halides (9a and 8b-d) in good yields. Treatment of the iodide (8a) with an excess of refluxing thionyl chloride gave 1,1,3-trichloro-4-methyl-4H-pyrrolo[1,2-a]benzimidazol-2(1H)-one (14). Introduction of electrophiles into the 1-position of 11d and 6-position of 5-methyl-9,10-dihydro-5H-azepino[1,2-a]benzimidazol-7(8H)-one (2a) was achieved by successive treatment with lithium diisopropylamide and electrophiles such as methyl iodide and ketones. The azepinone 2a was reacted with various electrophiles to give 6-substituted products in good yields.

• 公益社団法人日本薬学会の論文
• 1991-11-25

著者

• 太田 俊作

  Kyoto Pharmaceutical University

• 山下 正行

  Kyoto Pharmaceutical University

• 太田 俊作

  京都薬科大学薬学部

• 成田 善弘

  Kyoto Pharmaceutical University

• 畠山 祥子

  Kyoto Pharmaceutical University

• 湯浅 輝之

  Kyoto Pharmaceutical University

• 川崎 郁男

  Kyoto Pharmaceutical University

• 太田 俊作

  Kyoto College Of Pharmacy

• 成田 喜弘

  Kyoto Pharmaceutical University

• 小林 正和

  Kyoto Pharmaceutical University

• 海部 恭子

  Kyoto Pharmaceutical University

• 山下 正行

  京都薬科大学薬学部

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