ABSTRACT
The syntheses of N,N'-dibenzyl-2,4-diaminopyrimidine-2'-deoxyribonucleoside and 1-methyl-2'-deoxypseudoisocytidine via Heck coupling are described. A survey of the attempts to use the Heck coupling to synthesize N,N'-dibenzyl-2,4-diaminopyrimidine-2'-deoxyribonucleoside is provided, indicating a remarkable diversity in outcome depending on the specific heterocyclic partner used.
Subject(s)
Deoxycytidine/analogs & derivatives , Deoxycytidine/chemical synthesis , Deoxyribonucleosides/chemical synthesis , Pyrimidine Nucleosides/chemical synthesis , Deoxycytidine/chemistry , Deoxyribonucleosides/chemistry , Molecular Structure , Pyrimidine Nucleosides/chemistry , StereoisomerismABSTRACT
[structure: see text]. An efficient three-step synthesis of chiral 3H-quinazoline-4-one derivatives from commercial materials is disclosed. The Mumm reaction of imidoyl chloride with alpha-amino acids followed by reductive cyclization affords enantiomerically pure (ee >93%) quinazoline-4-ones in good overall yield. A comparison with existing approaches indicates that this method is superior for hindered substrates.
