I2-catalyzed one-pot oxidative condensation of thiourea, methyl ketones, and aryl thiols into 5-sulfenylated 2-amino-1,3-thiazoles by DMSO

A one-pot, efficient oxidative-condensation process for constructing both 4-alkyl and 4-aryl-5-(arylthio) thiazol-2-amines using DMSO/I-2 is introduced. In this procedure, methyl ketones, thiourea, DMSO, and thiols are reacted together in the presence of molecular 1 2 at 80 degrees C simply to produce 4-alkyl or aryl-5-(arylthio)thiazol-2-amines due to formation of a C-S bond between thiourea and methyl carbon linked to carbonyl group and the another C-S bond formation between thiol and thiazol ring. Under reaction conditions, both aryl and alkyl methyl ketones including acetophenone and substituted acetophenones also, 2-alkanones such as acetone, 2-butanone, 2-pentanone, and 2-heptanone yield those products successfully. [GRAPHICS] .

Automated summary

We present a one-pot, efficient oxidative-condensation process using DMSO/I-2 to construct 4-alkyl and 4-aryl-5-(arylthio) thiazol-2-amines. Various alkyl and aryl methyl ketones can be successfully synthesized under these reaction conditions.