Natural Product-Oriented Photo-Induced Denitrogenative Annulations of 1-Alkenylbenzotriazoles

Abstract

The photo-induced denitrogenative annulations of a variety of 1-alkenylbenzotriazoles were investigated. By judiciously manipulating the structural variations of 1-alkenylbenzotriazoles, two characteristic polycyclic skeletons associated with monoterpene indole alkaloids were constructed through a diverted and controllable manner. The present work not only enriches the photochemistry of 1-alkenylbenzotriazoles, but also offers a unified approach to access skeletally diverse indole alkaloid scaffolds.

Selective N–N or N–S bond cleavage of 1-trifluoromethyl benzotriazoles enables divergent synthesis of 1,2,4-benzotriazines and benzotriazoles

“…2 Even though great progress has been achieved in developing the denitrogenative functionalization of benzotriazoles (Fig. 1b), 15 the application of benzotriazoles as five-atom synthons in cycloaddition has rarely been reported. 16 As part of our ongoing research interest in developing novel methods to synthesize carbo-and heterocycles, 17 herein we disclose a base-promoted formal [5 + 1] cycloaddition of 1-trifluoromethyl benzotriazole and α-bromoacetophenone.…”