Issue 1, 2016

MoO2Cl2 catalyzed efficient synthesis of functionalized 3,4-dihydropyrimidin-2(1H)-ones/thiones and polyhydroquinolines: recyclability, fluorescence and biological studies

Abstract

A simple, facile and efficient synthesis of functionalized dihydropyrimidinones and polyhydroquinolines using molybdenum(VI) dichloride dioxide (MoO2Cl2) has been developed. The present protocol demonstrates the exceptional tolerance towards acid labile protecting groups such as tert-butyl dimethyl silyl (TBDMS) and tert-butyl diphenyl silyl (TBDPS). This is the first report of exploring Lewis acid properties of MoO2Cl2 in the diversity oriented synthesis of Biginelli and Hantzsch reactions. Biologically important and highly structured conjugates of dihydropyrimidinone and polyhydroquinoline derivatives containing coumarin, pyrazole, indole and triazole moieties were synthesized in good to excellent yields. Compound 4o exhibited blue fluorescence at a maximum UV absorbance λmax of 326 nm. In the preliminary MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] assay, compound 4n displayed remarkable cytotoxic activity against A549 and PC3 cell lines while compound 7q was found to be cytotoxic against HGC-27 and PC3 cancer cell lines.

Graphical abstract: MoO2Cl2 catalyzed efficient synthesis of functionalized 3,4-dihydropyrimidin-2(1H)-ones/thiones and polyhydroquinolines: recyclability, fluorescence and biological studies

Supplementary files

Article information

Article type
Paper
Submitted
11 Sep 2015
Accepted
09 Nov 2015
First published
30 Nov 2015

New J. Chem., 2016,40, 838-843

Author version available

MoO2Cl2 catalyzed efficient synthesis of functionalized 3,4-dihydropyrimidin-2(1H)-ones/thiones and polyhydroquinolines: recyclability, fluorescence and biological studies

S. D. Guggilapu, S. K. Prajapti, A. Nagarsenkar, G. Lalita, G. M. Naidu Vegi and B. N. Babu, New J. Chem., 2016, 40, 838 DOI: 10.1039/C5NJ02444G

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