One-pot regioselective synthesis of new 5-(arylsulfonylamino)imidazo[2,1-b]thiazoles

Abstract

N-(2,2-Dichloro-2-phenylethylidene)-4-chlorobenzenesulfonamide reacts with 2-aminothiazoles to give products of nucleophilic addition in good yields. The adducts are cyclized into the unexpected 5-(arylsulfonyl)amino-6-phenylimidazo[2,1-b]thiazoles in 70-75% yield; whereas the anticipated isomeric 6-(arylsulfonyl)amino-5-phenylimidazo[2,1-b]thiazoles were not observed.

Regioselective reaction of imidazole-2-thiols with N-sulfonylphenyldichloroacetaldimines: en route to novel sulfonylamino-substituted imidazo[2,1-b]thiazoles and thiazolo[3,2-a]benzimidazoles

“…11,[22][23][24] We are engaged in elaboration of approaches to the preparation of annulated imidazole derivatives containing synthetically important pharmacophoric sulfonylamino group. [25][26][27][28] It is a common knowledge that the sulfonamide compounds are intensively employed for drug design. [29][30][31][32] First of all, these are medicinally classical antagonists of folic acid having antimicrobial and antibiotic properties.…”

“…In continuation of our research, [25][26][27][28] here we have studied for the first time the reaction of imidazole-2-thiols with N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides 1 to elaborate the approach for the synthesis of novel sulfonylamino-substituted derivatives of imidazo [2,1-b]thiazole. N-Sulfonylimines 1 represent activated electron-deficient halogen-containing imines, which are effective reagents for a wide range of sulfonamide derivatives.…”