High Throughput Synthesis of 2,3,6-Trisubstituted-5,6-Dihydroimidazo[2,1-b]thiazole Derivatives

A facile approach to the synthesis of 2,3,6-trisubstituted-5,6-dihydroimidazo[2,1-b]thiazole was reported. A resin bound cyclic thiourea was formed by the treatment of a resin bound diamine with 1,1'-thiocarbonyldiimidazole, and then reacted with a α-haloketone to generate a resin bound isothiourea. HF treatment of the resin bound isothiourea resulted in the cleavage of the product and simultaneous formation of an enamine bond. This led to the formation of the 2,3,6-trisubstituted-5,6-dihydroimidazo[2,1-b]thiazole in high yield and purity.