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Updated: Oct 15, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Functionalized Polyhydroquinolines from Amino Acids Using a Key One-Pot Cyclization Cascade and Application to the
Shawn Gallagher-Duval1, Vincent Lapointe1, Guillaume Bélanger1
1Département de chimie, Université de Sherbrooke, 2500, boulevard de l'Université, Sherbrooke, Québec, Canada J1K 2R1.
Abstract:
Substituted polyhydroquinolines are ubiquitous skeletal cores found in drugs and bioactive natural products. As a new route to access this motif, we successfully developed a one-pot cyclization cascade with high chemocontrol and diastereoselectivity. The sequence generates two cycles, three carbon-carbon bonds, and an all-carbon quaternary center in a highly convergent process. Functionalized polyhydroquinolines and congeners can be accessed from commercially available amino acids. This versatile and robust strategy was applied to the synthesis of (±)-Δ7-mesembrenone.
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