A novel protocol for the facile construction of tetrahydroquinoline fused tricyclic frameworks via an intramolecular 1,3-dipolar nitrile oxide cycloaddition reaction?

Organic & Biomolecular Chemistry Pub Date: 2015-08-12 DOI: 10.1039/C5OB01060H

Abstract

An efficient method towards the synthesis of quinoline fused tricyclic compounds involving an intramolecular 1,3-dipolar nitrile oxide cycloaddition reaction utilizing Baylis–Hillman derivatives in good yields has been described for the first time. A highly functionalized tricyclic framework was created by forming two rings and two adjacent stereocentres through the formation of two N–C bonds, one C–C bond and one O–C bond in a highly regio and diastereoselective manner.

Graphical abstract: A novel protocol for the facile construction of tetrahydroquinoline fused tricyclic frameworks via an intramolecular 1,3-dipolar nitrile oxide cycloaddition reaction
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