(Propargylsulfanyl)-2-aza-1,3,5-trienes as a direct source for novel family of highly functionalized 4,5-dihydro-1,3-thiazoles

Add time:07/13/2019    Source:sciencedirect.com

A novel, simple approach to 2-(1-alkoxyprop-1-enyl)-5-ethenylidene-4,5-dihydro-1,3-thiazoles has been disclosed through the reaction of (propargylsulfanyl)-2-aza-1,3,5-trienes (readily available from alkoxyallenes, isothiocyanates, and propargyl bromide) with potassium or sodium tert-butoxide (1.1–1.4 equiv) under mild conditions [DMSO/THF (∼1:4–5), ca. −30 °C, 15–30 min]. The process proceeds through deprotonation of an activated SCH2 group, followed by intramolecular [1,5]-ring-closure. Unlike alkyl-, benzyl-, and allylsulfanyl-analogues, the exclusive or competitive formation of seven-membered azaheterocycles was not observed.

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