Unexpected reactivity of Imidazo[2,1-b]thiazolines with organometallic reagents.
[reaction: see text] 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.
Sisko
J
J
SmithKline Beecham Pharmaceuticals, Synthetic Chemistry Department, 709 Swedeland Road, PO Box 1539, King of Prussia, Pennsylvania 19406, USA. joe_sisko-1@sbphrd.com
Kassick
A J
AJ
Shetzline
S B
SB