Res Chem Intermed (2017) 43:2985–3005 DOI 10.1007/s11164-016-2807-1 Structurally diversiﬁed synthesis of 2,3-dihydroquinazolin-4-(1H)-ones from 2-aminobenzamides and 1,2-dicarbonyl compounds in ionic liquids catalyzed by iodine 1 1 1 • • Jie Wang Mei-Mei Zhang Xiang-Shan Wang Received: 10 July 2016 / Accepted: 8 November 2016 / Published online: 24 November 2016 Springer Science+Business Media Dordrecht 2016 Abstract A green procedure for the rapid diversiﬁcation of quinazolin-4-(1H)-one scaffolds is described in this paper. Various types of 1,2-dicarbonyl compounds are treated with 2-aminobenzamides in ionic liquids catalyzed by iodine and unexpectedly afford structurally diversiﬁed single-quinazoline derivatives. The recyclability of the ionic liquids makes this protocol to be an environmentally benign procedure. Graphical Abstract A total of 39 quinazolin-4-(1H)-one scaffolds were synthesized via a green procedure of 1,2-dicarbonyl compounds and 2-aminobenzamides in ionic liquids catalyzed by iodine. O O O R R R N N N R' R' R' H H H NH NH NH 2 2 2 O O O O O O O O R = 2 H R = 4-MeOC H = R = H -BrC 6 4 R 4-FC H CH 4-MeC R = 4-MeC H CH 6 4 6 4 2 6 4 6 4 2 R' 5-Br R'
Research on Chemical Intermediates – Springer Journals
Published: Nov 24, 2016
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