Journal
NEW JOURNAL OF CHEMISTRY
Volume 39, Issue 3, Pages 2323-2332Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4nj02155j
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- CNPq
- FAPERJ
- CAPES
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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 beta-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 pK(a) determination make these compounds a good start point for new chemical and biological probes as well as useful pH indicators.
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