Divergent Construction of Benzothiophene-Fused N-Heterocycles via Stereotunable Three-Component Domino Reactions
Qingsong Deng, Aimin Yu, Lei Zhang, Xiangtai Meng
Abstract
A stereotunable three-component domino strategy among thioisatin, 2-bromo-1-phenylethan-1-one, and cyclohexane-1,2-diamine under catalyst-free conditions was disclosed. A wide range of benzothiophene-fused polycycles and eight-membered N-heterocycles were synthesized by regulating the stereoconfiguration of cyclohexane-1,2-diamines. The detailed mechanism and the origin of the chemoselectivity were explored by density functional calculations. Analysis of the geometrical structures of key transition states revealed that the existence of favorable intramolecular attractions, and the steric effect governed the chemoselectivity observed.
Topics & Concepts
BenzothiopheneChemoselectivityChemistryIntramolecular forceCyclohexaneSteric effectsDominoTransition stateCatalysisDiamineComponent (thermodynamics)Combinatorial chemistryStereochemistryOrganic chemistryThermodynamicsPhysicsThiopheneMulticomponent Synthesis of HeterocyclesSynthesis of heterocyclic compoundsSynthesis and biological activity