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Updated: Jul 31, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Secondary Amine-Mediated Domino Reaction for the Synthesis of Substituted Quinolines from Dicyanoalkenes and Enynals
Yujiro Hayashi1, Xiaolei Han1, Naoki Mori1
1Department of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aza-Aoba, Aramaki, Aoba-ku, Sendai, 980-8578, Japan.
Abstract:
Substituted quinolines, tricyclic and tetracyclic molecules with a quinoline moiety are synthesized by a domino reaction from dicyanoalkenes and 3-aryl-pent-2-en-4-ynals in one pot. We established two methods: one is catalyzed by chiral diphenylprolinol silyl ether, and the other is catalyzed by di(2-ethyl)hexylamine, in combination with p-nitrophenol. A wide variety of dicyanoalkenes can be employed. As the catalysts are secondary amines, and water is the only by-product, this is an environmentally benign synthetic method for the preparation of substituted quinolines.
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