Application of β-Oxodithioesters in Domino and Multicomponent Reactions: Facile Route to Dihydropyrimidines and Coumarins

A facile route to hitherto unknown 5-methylmercaptothiocarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones and substituted 2H-chromene-2-thiones has been developed. SnCl2-catalyzed cyclocondensation of β-oxodithioesters with a variety of readily accessible aldehydes and urea affords the dihydropyrimidin...

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Veröffentlicht in:Journal of organic chemistry 2009-04, Vol.74 (8), p.3141-3144
Hauptverfasser: Singh, Okram Mukherjee, Devi, Nepram Sushuma
Format: Artikel
Sprache:eng
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Zusammenfassung:A facile route to hitherto unknown 5-methylmercaptothiocarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones and substituted 2H-chromene-2-thiones has been developed. SnCl2-catalyzed cyclocondensation of β-oxodithioesters with a variety of readily accessible aldehydes and urea affords the dihydropyrimidinones. The methodology involves the three-component Biginelli reaction. On the other hand, substituted salicylaldehyde and β-oxodithioesters reacted under the same condition to afford the substituted 2H-chromene-2-thiones in high yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo802585b