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Direct synthesis of 2,4,5-trisubstituted imidazoles and di/tri-substituted pyrimidines via cycloadditions of α,β-unsaturated ketones/aldehydes and N′-hydroxyl imidamides

Author:
Wu, Ping, Zhang, Xueguo, Chen, Baohua
Source:
Tetrahedron letters 2019 v.60 no.16 pp. 1103-1107
ISSN:
0040-4039
Subject:
aldehydes, chemical structure, cycloaddition reactions, imidazoles, ketones, pyrimidines
Abstract:
An efficient route for the synthesis of 5-acetylimidazoles and di/trisubstituted pyrimidines via iron-catalyzed cross-dehydrogenative coupling (CDC), with excellent tolerance and yields, has been developed. In this report, α,β-unsaturated aldehydes/ketones and N′-hydroxyl imidamides undergo [3+2] and [3+3] cycloadditions in two processes, involving iron-mediated Michael reaction, Robinson Annulation and 1,5-electrocyclization.
Agid:
6345562