2-Oxo-2-polyfluoroalkylethane-1-sulfones and -sulfamides in the three-component reactions leading to pyrimidine derivatives

Abstract

2-Oxo-2-polyfluoroalkylethane-1-sulfones and -sulfamides undergo Biginelli reaction with aryl aldehydes and (thio)urea to give 4-hydroxy-4-polyfluoroalkyl-5-sulfonyl-6-aryltetrahydropyrimidin-2(1H)-(thi)ones, whereas three-component reaction with urea and trialkyl orthoformate provides 4-hydroxy-4-polyfluoroalkyl-5-sulfonyl-3,4-dihydropyrimidin-2(1H)-ones. Some chemical properties of the synthesized pyrimidinones are discussed.

Recent synthetic methodologies for pyrimidine and its derivatives

“…In the following year, a one-step synthetic route to tetrahydropyrimidinones 59 (50%-85% yield) was presented by Timoshenko and colleagues via the condensation of urea 8/thiourea 58, aryl aldehyde 36, and a solution of ketosulfone/ketosulfamide 57 under acidic conditions (Scheme 14). 30 Most of the pyrimidine synthetic routes are limited because of poisonous byproducts, use of metal triflates, excess amounts of bases, etc. Jain et al synthesized pyrano [2,3-d] Ibrahim and El-Metwally synthesized pyrimidine derivatives by the treatment of acetoacetanilides 83, 2,4-dihydroxy benzaldehyde 84, and thiourea 58 in the presence of ethanol and conc.…”