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Synfacts 2007(7): 0684-0684  
DOI: 10.1055/s-2007-968679
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2-Formylpyrroles via Heterocyclic Interconversion

Contributor(s): Victor Snieckus, Wei Gan
J. T. Reeves*, J. J. Song, Z. Tan, H. Lee, N. K. Yee, C. H. Senanayake
Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, USA
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Publication History

Publication Date:
22 June 2007 (online)

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Significance

A heterocyclic interconversion of 5-substituted oxazoles into 2-formylpyrroles is reported. The aldol condensation products, resulting from treatment of ketones with 4-formyloxa­zoles, upon mesylation and mild base treatment, afford 2-formylpyrroles with alkyl, aryl, and alkenyl substituents. Furthermore, halogenated hetero­cycles may be incorporated which may allow further functionalization. This methodology was extended to the interconversion of a formylthiazole into an N-substituted 2-formylpyrrole.