Issue 17, 2018

An unprecedented tandem synthesis of fluorescent coumarin-fused pyrimidines via copper-catalyzed cross-dehydrogenative C(sp3)–N bond coupling

Abstract

An efficient, one-pot Cu-catalyzed tandem synthesis of fluorescent 1-benzyl-2-phenyl-1,2-dihydro-5H-chromeno[4,3-d]pyrimidin-5-ones from 4-chloro-3-formylcoumarin and benzylamines was developed by in situ intramolecular cross-dehydrogenative C(sp3)–N bond formation in moderate-to-good yields under ligand-free ambient conditions. This synthesis was easily scalable, and the generality of the substrates was established. These coumarin-fused pyrimidines exhibited interesting photo-physical properties and high quantum yields, and would be potential candidates for facilitating suitable studies in medicinal chemistry and materials science.

Graphical abstract: An unprecedented tandem synthesis of fluorescent coumarin-fused pyrimidines via copper-catalyzed cross-dehydrogenative C(sp3)–N bond coupling

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
08 Mar 2018
Accepted
05 Apr 2018
First published
05 Apr 2018

Org. Biomol. Chem., 2018,16, 3220-3228

An unprecedented tandem synthesis of fluorescent coumarin-fused pyrimidines via copper-catalyzed cross-dehydrogenative C(sp3)–N bond coupling

S. Kumari, S. M. A. Shakoor, S. Khullar, S. K. Mandal and R. Sakhuja, Org. Biomol. Chem., 2018, 16, 3220 DOI: 10.1039/C8OB00586A

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