Catalyst-free one-pot regioselective synthesis of benzo[d]imidazo[2,1-b]thiazoles by heating or grinding

摘要

Eco-friendly, efficient, and simple one-pot catalyst-free new procedures have been reported for the synthesis of benzo[d]imidazo[2,1-b]thiazoles by condensation of phenylglyoxal, cyclic enolizable carbonyl compounds, and 2-aminobenzothiazole at 80 degrees C or by grinding the components at room temperature in glycerol. Cyclic enolizable carbonyl compounds employed in the protocol include dimedone, cyclohexa-1,3-dione, cyclopenta-1,3-dione, 5-methylcyclohexa-1,3-dione, and 4-hydroxy-6-methyl-2-pyrone. All the reactions were complete in similar to 30 min. The structures of all the products were confirmed by spectral data. The structures of compounds IVl and IVe have also been confirmed by X-ray crystallographic studies. This protocol offers advantages such as short reaction time, easy workup, high yields and an environmentally benign methodology.