Acid-catalyzed One Pot Synthesis of Thiazolo[4,5-b]indolamines from alpha-Diazoimidamides and Thioureas

A novel synthetic method for the formation of thiazolo[4,5-b]indol-2-amines from alpha-diazoimidamides and mono-substituted thioureas in the presence of a catalytic amount of boron trifluoride etherate and camphorsulfonic acid under mild conditions was demonstrated. This methodology has a wide-ranging scope of alpha-diazoimidamides and mono-substituted thioureas, amenable for upscaling experiments and further transformation.

Automated summary

A new synthetic method for the formation of thiazolo[4,5-b]indol-2-amines from alpha-diazoimidamides and mono-substituted thioureas was demonstrated. The reaction was catalyzed by boron trifluoride etherate and camphorsulfonic acid under mild conditions. This methodology is suitable for various alpha-diazoimidamides and mono-substituted thioureas, and can be scaled up for further experiments and transformation.