Download PDF
Synlett 1997; 1997(9): 1063-1064
DOI: 10.1055/s-1997-1552
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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)

      >