Synthesis of N-Formyl-2-benzoyl Benzothiazolines, 2-Substituted Benzothiazoles, and Symmetrical Disulfides from N-Phenacylbenzothiazolium Bromides.

An unusual aerobic hydrolysis-cascade reaction has been developed with N-phenacylbenzothiazolium bromides by treatment with organic and inorganic base. The corresponding N-formyl-2-benzoyl benzothiazoline and 2-substituted benzothiazole products were obtained in moderate to good yields under mild reaction conditions. Also, symmetrical disulfide was formed when keto group was replaced with ester. The scopes of the reactions are fairly broad tolerating aryl, heteroaryl, and alkyl groups.