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Updated: Apr 2, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Thermal Dearomative Rearrangement of α-(Prop-2-enyl)-α'-(pyridin-2-yl) Malonate Derivatives toward
Pierre Locquet1, Noam Boussalem1, Delphine Hatey1
1Université de Strasbourg, CNRS, Institut de Chimie, UMR 71774 Rue Blaise Pascal, CS 90032, 67081 Strasbourg, France.
Abstract:
Reported herein is a thermally induced dearomative rearrangement of α-(aza-heteroaryl)-α'-prop-2-enyl malonate derivatives, affording 4H-dihydroquinolizine derivatives (21 examples, 26-89%). The rearrangement, assisted by microwave heating, afforded diastereoselective quinolizidine scaffolds, known for their broad biological activities. Experimental results and DFT calculations converge to support a stepwise mechanism initiated by intramolecular [1,4]-addition of pyridine nitrogen to the activated acrylate moiety followed by selective ester transfer.
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