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Synthesis 2006(12): 1975-1980  
DOI: 10.1055/s-2006-942390
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© Georg Thieme Verlag Stuttgart · New York

Investigations into the Parallel Synthesis of Novel Pyrrole-Oxazole Analogues of the Insecticide Pirate

Wendy A. Loughlin*a,b, Luke C. Hendersona, Kathryn E. Elsona, Michelle E. Murphya
a School of Science, Griffith University, Brisbane, QLD, 4111, Australia
b Eskitis Institute for Cell and Molecular Therapies, Griffith University, Brisbane, QLD, 4111, Australia
Fax: +61(7)37357656; e-Mail: w.loughlin@griffith.edu.au;
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Publication History

Received 12 January 2006
Publication Date:
11 May 2006 (online)

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Abstract

Investigations into the parallel synthesis of selected analogues of a structurally unique pyrrole-oxazole analogue of the pyrrole insecticide pirate, are reported. Acylaminoketone salts were obtained from ketobromides in moderate to high yields and excellent purity. A number of N-tosyl pyrroles were obtained; however, formation of the target acyl tosyl pyrroles was thwarted by the stereoelectronic effects of the pyrrole substituents. During the pyrrole subunit chemistry, an interesting pyrrole derivative, vinyl pyrrole, was isolated. By restricting diversity to the aryl subunit, the parallel synthesis of selected pyrrole-oxazoles in moderate purity, was achieved when electron-donating or no groups were present on the aryl ring.

Key words

pyrroles - oxazoles - amines - cyclizations - parallel synthesis