Synthesis of benzo-γ-carboline alkaloid cryptosanginolentine by reaction of indole-2,3-dicarboxylic anhydrides with anilines |
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Authors: | Yasuyoshi Miki Makoto Kuromatsu Hideaki Miyatake Hiromi Hamamoto |
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Affiliation: | aSchool of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi-Osaka 577-8502, Japan |
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Abstract: | 1-Benzenesulfonylindole-2,3-dicarboxylic anhydride was reacted with aniline to give the 2-carbamoylindole-3-carboxylic acid as the sole product, but with N-methylaniline, the 3-carbamoylindole-2-carboxylic acid was the major product, which could be transformed into the 1-benzenesulfonylbenzo-γ-carbolinone in the presence of Pd(OCOCF3)2. The reduction of the benzo-γ-carbolinone with LiAlH4 gave the cryptosanginolentine in high yield. |
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