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On-Water Synthesis of 2-Substituted Quinolines from 2-Aminochalcones Using Benzylamine as the Nucleophilic Catalyst

So Young Lee, Cheol-Hong Cheon*

*Department of Chemistry, Korea University, 145 Anam-ro, Seongbuk-gu, Seoul 02841, Republic of Korea, Email: cheonkorea.ac.kr

S. Y. Lee, C.-H. Cheon, J. Org. Chem., 2018, 83, 13036-13044.

DOI: 10.1021/acs.joc.8b01675 (free Supporting Information)


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Abstract

Benzylamine as the nucleophilic catalyst enables an on-water synthesis of 2-substituted quinolines in excellent yields from 2-aminochalcone derivatives. This protocol offers simple operation, broad substrate scope, good functional group tolerance, easy product isolation by simple filtration, recycling of the catalyst, and gram-scale synthesis.

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proposed mechanism



Key Words

quinolines


ID: J42-Y2018