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Synlett 1997; 1997(9): 1063-1064
DOI: 10.1055/s-1997-1552
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A New Two-Step Preparation of Pyrroles from β-Amino Ketones Utilizing Trimethylsilyldiazomethane

Tsutomu Yagi, Toyohiko Aoyama1 , Takayuki Shioiri2
  • 1Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467, JAPAN, Fax: +81-52-834-4172
  • 2Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467, JAPAN, Fax: +81-52-834-4172; E-mail: shioiri@phar.nagoya-cu.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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Lithium trimethylsilyldiazomethane smoothly reacted with N-substituted β-amino ketones to give 2-pyrrolines which were easily converted to the corresponding pyrroles by treatment with MnO2 (CMD, chemical manganese dioxide). The reaction with N,N-disubstituted β-amino ketones followed by oxidation with CMD also afforded pyrroles.

trimethylsilyldiazomethane - alkylidene carbene - β-amino ketone - 2-pyrroline - pyrrole - chemical manganese dioxide (CMD)