PDF herunterladen
Synthesis 1988; 1988(12): 999-1001
DOI: 10.1055/s-1988-27785
communication
© 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.

Synthesis of N-Substituted Pyrroles From Azlactones via 1,3-Oxazolium 5-Oxides

Fred. M. Hershenson* , Michael R. Pavia
  • *Department of Chemistry, Parke-Davis Pharmaceutical Research Division, Warner-Lambert Company, 2800 Plymouth Road, Ann Arbor MI 48105, USA
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
20. August 2002 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

In situ N-alkylation of azlactones (1,3-oxazol-5(4H)-ones) with reactive alkylating agents has been successfully accomplished. The resulting mesoionic 1,3-oxazolium 5-oxides (munchnones) are further transformed into N-alkylated pyrroles via a 1,3-dipolar cycloaddition reaction with a dipolarophile (dimethyl acetylenedicarboxylate) in the presence of 2,6-di-tert-butylpyridine.