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Synthesis of (4S*,5S* )-diphenyl-1,3,4,5-tetrahydro-2H-[1]benzopyrano [4,3-d]pyrimidine-2-thiones by base-catalysed cyclocondensation of (E)-3-benzylideneflavanones with thiourea, and determination of their monoacetylation site
A K MALLIK, F CHATTOPADHYAY, D K DEY, A PATRA
Published in -
2004
   
Issue: 3
Pages: 180 - 182
Abstract
Base-catalysed cyclocondensation of (E)-3-benzylideneflavanones with thiourea has been found to be highly stereoselective, producing (4S*,5S*)-diphenyl-1,3,4,5-tetrahydro-2H-[1]benzopyrano[4,3-d] pyrimidine-2-thiones in high yield, the structure of one of which has been determined by X-ray crystallography. Just like 4,6-diaryl-3, 4-dihydropyrimidine-2(1H)-thiones, the said products also undergo monoacetylation on treatment with AC2O. The site of acetylation in both of these classes of compound are established by detailed NMR spectral studies.
About the journal
JournalJournal of Chemical Research
Publisher-
ISSN0308-2342