Diastereoselective syntheses of 3-aryl-5-(arylalkyl)-6-methyl-1-(1-phenylethyl)thioxotetrahydropyrimidin-4(1H)-ones: a stereochemical perspective from endo and exocyclic chiral centres.
Diastereoselective syntheses of 3-aryl-(S/R)-6-methyl-1-[(S/R)-1-phenylethyl)]-2-thioxotetrahydro pyrimidin-4(1H)-ones were achieved in good yields by the condensation of aryl isothiocyanates with ethyl 3-(1-phenylethylamino)butanoate in a one-pot reaction. Benzylation of these substrates illustrated that the orientations of the exocylic and endocylic groups determine the stereochemical outcome of the product formed.
Kumar
Varun
V
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Sector 67, Mohali, Punjab 160 062, India.
Raghavaiah
Pallepogu
P
Mobin
Shaikh M
SM
Nair
Vipin A
VA
D015394:Molecular Structure; D011744:Pyrimidinones / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D011744:Pyrimidinones; C505709:tetrahydropyrimidinone