Tetrahedron

N–H Insertion reactions of rhodium carbenoids. Part 5: A convenient route to 1, 3-azoles

JR Davies, PD Kane, CJ Moody

Index: Davies, James R.; Kane, Peter D.; Moody, Christopher J. Tetrahedron, 2004 , vol. 60, # 18 p. 3967 - 3977

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Citation Number: 108

Abstract

Dirhodium (II) carboxylate catalysed reaction of diazocarbonyl compounds in the presence of primary amides results in the formation of α-acylaminoketones (12 examples) by N–H insertion reaction of the intermediate rhodium carbene. The 1, 4-dicarbonyl compounds are readily converted into structurally diverse oxazoles (11 examples) by cyclodehydration, thiazoles (10 examples) by treatment with Lawesson's reagent, or imidazoles (2 examples ...