Application of beta-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. SnCl(2)-catalyzed cyclocondensation of beta-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 beta-oxodithioesters reacted under the same condition to afford the substituted 2H-chromene-2-thiones in high yields.
Singh
Okram Mukherjee
OM
Department of Chemistry, Manipur University, Canchipur-795003, India. ok_mukherjee@yahoo.co.in
Devi
Nepram Sushuma
NS
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004952:Esters / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship; D013871:Thiones / Q000138:chemical synthesis / Q000737:chemistry; D014508:Urea / Q000138:chemical synthesis / Q000737:chemistry
D000447:Aldehydes; D001578:Benzopyrans; D003374:Coumarins; D004952:Esters; D011743:Pyrimidines; D013871:Thiones; C013243:salicylaldehyde; D014508:Urea