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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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Publication details

The article was received on 26 Nov 2014, accepted on 15 Jan 2015 and first published on 16 Jan 2015


Article type: Paper
DOI: 10.1039/C4NJ02155J
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Citation: New J. Chem., 2015,39, 2323-2332

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    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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