Modular and Stereoselective Approach to Highly Substituted Indole/Pyrrole-Fused Diazepanones
Shutao Wang, Siyu Wang, Shaoli Song, Qiansong Gao, Chunxi Wen, Zhuoqi Zhang, Lianyou Zheng, Jinbao Xiang
Abstract
A one-pot synthetic method for indole/pyrrole-fused 1,4-diazepanone scaffolds has been developed. This method involves a sequential amide coupling/intramolecular aza-Michael addition of 1H-indole/pyrrole-2-carboxylic acids with Morita–Baylis–Hillman-derived allylamines. The readily available starting materials, good stereoselectivity, and gram-scale synthesis make this method valuable for the construction of highly substituted fused heterocycles containing the 1,4-diazepanone moiety.
Topics & Concepts
StereoselectivityMoietyIndole testPyrroleIntramolecular forceChemistryCombinatorial chemistryAmideStereochemistryOrganic chemistryCatalysisAsymmetric Synthesis and CatalysisChemical synthesis and alkaloidsSynthesis and Characterization of Pyrroles