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NNN pincer Ru(II)-catalyzed dehydrogenative coupling of 2-aminoarylmethanols with nitriles for the construction of quinazolines

Author:
Wan, Xiao-Min, Liu, Zi-Lin, Liu, Wan-Qing, Cao, Xiao-Niu, Zhu, Xinju, Zhao, Xue-Mei, Song, Bing, Hao, Xin-Qi, Liu, Guoji
Source:
Tetrahedron 2019 v.75 no.18 pp. 2697-2705
ISSN:
0040-4020
Subject:
chemical structure, dehydrogenation, nitriles, oxidation, reaction mechanisms, ruthenium
Abstract:
An efficient NNN pincer Ru(II)-catalyzed preparation of quinazolines via acceptorless dehydrogenative strategy has been developed. Under the optimized conditions, a broad range of substituted o-aminobenzyl alcohols and (hetero)aryl or alkyl nitriles were well tolerated to afford various 2-substituted quinazolines in high yields. Subsequently, a set of control experiments have been performed to elucidate the reaction mechanism, which underwent alcohol oxidation, nitrile hydration, and cyclocondensation steps. The current protocol is featured with several advantages, such as environmental benignity, operational simplicity, broad substrate scope (compatible with aliphatic nitriles, up to 87% yield), and short reaction time (mostly in 2 h).
Agid:
6357930