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Issue 3, 2015
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Synthesis and mechanism of novel fluorescent coumarin–dihydropyrimidinone dyads obtained by the Biginelli multicomponent reaction

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Abstract

The optimization of a Biginelli Multicomponent Reaction (MCR) protocol for obtaining a collection of 3,4-dihydropyrimidin-2(1H)-one/thione, with UV absorption and blue fluorescent properties, from synthetic coumarin beta-ketoester derivatives is described. This is the first report of Biginelli adducts bearing a coumarin nucleus in the β-ketoester moiety and their MCR mechanism seems to pass through a Knoevenagel intermediate, which was considered as unlikely before. A chemical library was obtained and the dihydropyrimidin-2(1H)-one nucleus formation confirmed by X-ray diffraction. Photophysical analyses of representative compounds in different solvents show good Stokes shifts in water that are associated to a postulated ICT process and pKa determination make these compounds a good start point for new chemical and biological probes as well as useful pH indicators.

Graphical abstract: Synthesis and mechanism of novel fluorescent coumarin–dihydropyrimidinone dyads obtained by the Biginelli multicomponent reaction

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Supplementary files

Article information


Submitted
26 Nov 2014
Accepted
15 Jan 2015
First published
16 Jan 2015

New J. Chem., 2015,39, 2323-2332
Article type
Paper
Author version available

Synthesis and mechanism of novel fluorescent coumarin–dihydropyrimidinone dyads obtained by the Biginelli multicomponent reaction

F. Vitório, T. M. Pereira, R. N. Castro, G. P. Guedes, C. S. Graebin and A. E. Kümmerle, New J. Chem., 2015, 39, 2323
DOI: 10.1039/C4NJ02155J

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