Synthesis 2003(13): 1959-1961
DOI: 10.1055/s-2003-41020
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

A Convenient Synthesis of N-Acylpyrroles from Primary Aromatic Amides

Anil R. Ekkati, Dallas K. Bates*
Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USA
Fax: +1(906)4872061; e-Mail: dbates@mtu.edu;
Further Information

Publication History

Received 20 May 2003
Publication Date:
19 August 2003 (online)

Abstract

Synthesis of N-acylpyrroles in 45-85% isolated yield from primary aromatic amides and excess 2,5-dimethoxytetrahydrofuran in presence of one equivalent of thionyl chloride is reported. This method has several advantages including short reaction times, mild reaction conditions, and easy workup. The technique works particularly well for deactivated aromatic amides.

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For example, benzamide in this reaction mixture (50-60 °C) formed N-benzoylindole and N-benzoylpyrrole after 5 h in 75% and 17% yield (GC), respectively.