I<sub>2</sub>-DMSO Mediated Multicomponent [3+2] Annulation Reaction: An Approach to Pyrrolo[2,1-<i>a</i>]isoquinoline Derivatives with a Quaternary Center
Shi‐Yi Zhuang, Jin-Yi Liu, Hui Guo, Yong‐Xing Tang, Xiang‐Long Chen, Jin‐Tian Ma, Yan‐Dong Wu, An‐Xin Wu, Kai‐Lu Zheng
Abstract
An I2-DMSO mediated multicomponent [3+2] cascade annulation reaction using methyl ketones, 1,2,3,4-tetrahydroisoquinolines (THIQ) and cyclopropenones as readily available substrates has been developed. This metal-free process involves N–H/α-C(sp3)–H trifunctionalization of THIQ and C–C bond cleavage of cyclopropenone, providing a direct approach to obtain pyrrolo[2,1-a]isoquinoline derivatives with a quaternary carbon center. Two C–C bonds and one C–N bond are formed efficiently in one pot.
Topics & Concepts
IsoquinolineAnnulationChemistryQuaternary carbonBond cleavageCenter (category theory)Medicinal chemistryStereochemistryCombinatorial chemistryOrganic chemistryEnantioselective synthesisCrystallographyCatalysisCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSynthesis and Characterization of Pyrroles