Organic letters

Unexpected Reactivity of Imidazo [2, 1-b] thiazolines with Organometallic Reagents

J Sisko, AJ Kassick, SB Shetzline

Index: Sisko, Joseph; Kassick, Andrew J.; Shetzline, Steven B. Organic Letters, 2000 , vol. 2, # 18 p. 2877 - 2880

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Citation Number: 6

Abstract

The reaction of imidazo [2, 1-b] thiazolines with various organometallic reagents is described. Nucleophilic attack of organolithium reagents on sulfur occurs with extrusion of ethylene to produce 2-thioalkyl-or 2-thioarylimidazoles. The outcome with Grignard reagents, however, is less predictable, with some reagents adding at sulfur and others reacting at C-2 or not at all.