Metal-Free [5 + 1] Cycloaddition–Aromatization of Benzotriazoles and Sulfur Ylides to Construct 1,2,4-Benzotriazines
Xinyuan Wang, Jinhang Yu, Mengjiao Xu, Hui Mao, Yueyue Shan, Xin Lv, Liejin Zhou
Abstract
Reported herein is a novel [5 + 1] cycloaddition-aromatization of benzotriazoles and sulfur ylides to efficiently construct 1,2,4-benzotriazine derivates with good yield. This new protocol does not employ any transition metal reagent and enables the cycloaddition by cleavage of the N-N single bond. The use of inexpensive and readily available starting materials, a broad substrate scope, mild reaction conditions, metal-free, and versatile functionalization of the 1,2,4-benzotriazines make this strategy more attractive.
Topics & Concepts
CycloadditionAromatizationChemistryReagentSulfurYield (engineering)Combinatorial chemistrySubstrate (aquarium)Transition metalOrganic chemistryMetalCatalysisGeologyOceanographyMetallurgyMaterials scienceSulfur-Based Synthesis TechniquesClick Chemistry and ApplicationsCatalytic C–H Functionalization Methods