A versatile synthesis of dihydropyrimidinone C-nucleosides.
A versatile synthesis of N-substituted dihydropyrimidinone C-nucleosides (20-29) is described. Glycosyl amino esters (3-9), obtained by reductive alkylation of glycosyl amino esters 1 and 2, on condensation with different isocyanates afforded respective ureido derivatives (10-19) in good to quantitative yields. The latter on cyclative amidation with a combination of DBU/TBAB (tetrabutylammonium bromide)/4A molecular sieve gave the corresponding nucleosides (20-29) in good yields.
Mishra
Ram Chandra
RC
Medicinal Chemistry Division, Central Drug Research Institute, Lucknow, India.
Katiyar
Diksha
D
Tewari
Neetu
N
Tripathi
Rama Pati
RP
D000478:Alkylation; D004952:Esters / Q000737:chemistry*; D017953:Isocyanates / Q000737:chemistry; D015394:Molecular Structure; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*; D011744:Pyrimidinones / Q000737:chemistry*
D004952:Esters; D017953:Isocyanates; D011741:Pyrimidine Nucleosides; D011744:Pyrimidinones