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Updated: Jun 11, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Asymmetric Desymmetrization of para-Quinamines via (3+2) Cycloaddition With 1,3,5-Triazinanes
Xiangyu Wang1, Miao-Jiong Tang2, Zun Yang1
1Key Laboratory of Green Chemistry & Technology, College of Chemistry, Ministry of Education, Sichuan University, Chengdu, P. R. China.
Abstract:
Asymmetric catalytic synthesis of a number of hydrobenzoimidazoles was achieved from para-quinamines and 1,3,5-triazinane. A chiral rare-earth metal catalyst of N,N'-dioxide was disclosed to be efficient under mild reaction condition, benefiting the formal (3+2) cycloaddition in good yield and enantioselectivity with exclusively cis-diastereoselectivity. The enantioselectivity-determining step is an intramolecular aza-Michael reaction, and the optimized catalyst is absent from the existing database of the related asymmetric Michael reaction. The results lead to a useful supplement to the related database for prediction.
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