Synthesis of 3-amino-5H-pyrido(4,3-b)indoles, carcinogenic .GAMMA.-carbolines.

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概要

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• The carcinogenic γ-carbolines 3-amino-1,4-dimethyl-5<I>H</I>-pyrido[4,3-<I>b</I>]indole (<B>1</B>) and 3-amino-1-methyl-5<I>H</I>-pyrido[4,3-<I>b</I>]indole (<B>2</B>) were synthesized efficiently by the following procedures. The key method involved the acid-catalyzed cyclization of 2-acetamido-3-(2-indolyl)alkanoic acids to 1,2-dihydro-γ-carbolines. This was followed by dehydrogenation to the γ-carbolinecarboxylates and conversion of the ester group to the carboxyl and finally to the amino one by Curtius rearrangement. Alternative methods involved the thermolysis of 4-(1-benzotriazolyl)-3,6-dimethyl-2-pyridinamine to synthesize <B>1</B> and the condensation of 3-acetylindole-2- acetonitrile with ammonia to synthesize <B>2</B>. The structures of γ-carbolines <B>1</B> and <B>2</B> were unambiguously established by comparing samples of each synthesized by the two different routes. A selective and one-step synthesis of ethyl 2-acetamido-3-(2-indolyl)alkanoates was newly exploited starting from diethyl acetamidomalonate and quaternary ammonium salts of 2-[1-(dimethylamino)alkyl]indoles.

• 公益社団法人 日本化学会の論文

著者

• Nomura Hiroaki

  Central Research Division, Takeda Chemical Ind., Ltd.

• Akimoto Hiroshi

  Central Research Division, Takeda Chemical Ind., Ltd.

• Kawai Akiyoshi

  Central Research Division, Takeda Chemical Ind., Ltd.

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• Synthesis of 3-amino-5H-pyrido(4,3-b)indoles, carcinogenic .GAMMA.-carbolines.

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