Journal
TETRAHEDRON
Volume 60, Issue 18, Pages 3967-3977Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2004.03.037
Keywords
heterocyclic; oxazole; thiazole; imidazole
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Dirhodium(II) carboxylate catalysed reaction of diazocarbonyl compounds 2 in the presence of primary amides 1 results in the formation of alpha-acylaminoketones 3 (12 examples) by N-H insertion reaction of the intermediate rhodium carbene. The 1,4-dicarbonyl compounds 3 are readily converted into structurally diverse oxazoles 4 (11 examples) by cyclodehydration, thiazoles 5 (10 examples) by treatment with Lawesson's reagent, or imidazoles 6 (2 examples) by reaction with ammonia or methylamine. (C) 2004 Elsevier Ltd. All rights reserved.
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