Portal de Periódicos da CAPES

Synthesis and exchange reactions of 5‐alkyl‐2‐oxo‐6‐thioxo‐1,2,3,6‐hexahydropyrimidine‐4‐carboxylic acids

1997; Wiley; Volume: 34; Issue: 4 Linguagem: Inglês

10.1002/jhet.5570340444

1943-5193

Craig A. Batty, Michael K. Manthey, Julie Kirk, Monika Manthey, Richard I. Christopherson, Trevor W. Hambley,

Synthesis and Characterization of Heterocyclic Compounds

Abstract An improved preparation of 2‐oxo‐6‐thioxo‐1,2,3,6‐hexahydropyrimidine‐4‐carboxylic acid 3, a potent inhibitor of dihydroorotase is presented. Trans ‐5‐alkyl‐2‐oxo‐6‐thioxohexahydropyrimidine‐4‐carboxylic acids 12a‐c were synthesised via the thiation of the p ‐methoxybenzyl esters of 5‐alkyldihydroorotic acids with Lawesson's reagent followed by subsequent de‐protection. The corresponding cis isomers were prepared by reduction of 5‐alkyl‐6‐thioxoorotic acids with zinc in acetic acid. The stability and exchange reactions of 12a‐c under physiological conditions were investigated by ultra‐violet and 1 H nmr spectroscopy. The attempted synthesis of 16 , a fused cyclopentyl derivative of 3 is also presented.