Studies on reactions of pyrimidine compounds: Synthesis and reactions of 5-benzoyl-4,6-diphenyl-1,2,3,4-tetrahydro-2-thioxopyrimidine


Aslanoglu F., Akbas E., SOENMEZ M., ANIL B.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, vol.182, no.7, pp.1589-1597, 2007 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 182 Issue: 7
  • Publication Date: 2007
  • Doi Number: 10.1080/10426500701263554
  • Journal Name: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.1589-1597
  • Keywords: Biginelli reaction, cyclocondensation, multicomponent reaction, one-pot condensation reactions, synthesis, tetrahydropyrimidine, CALCIUM-CHANNEL BLOCKERS, ACID-ESTERS, POTENT MIMICS, DERIVATIVES

Abstract

The 5-benzoyl-4,6-diphenyl-1,2,3,4-tetrahydro-2-thioxopyrimidin (1) have been prepared via Biginelli cyclocondensation reaction in acetic acid under reflux condition in good yield (93%). Reactions of 1 and iodomethane to afford thiopyrimidine compounds 3 and 5. Also, the acetylation of compounds 1 and 3 gave 3-acetyl thioxopyrimidine 2 and methylthiopyrimidine 4, respectively. Thioxopyrimidine derivative 6 was synthesized from 1 and POCl3/DMF Furthermore, the starting compound 1 were cyclized with various bromo compounds to the thiazolopyrimidine 7, 8, 9 and pyrimido[2,3-b]thiazine10 derivatives, in approximately 55-78% yields. The purpose of synthesizing the thioxopyrimidine derivatives is because of the high biological activities. All of these derivatives have been characterized by analytical and spectroscopic studies and the reaction mechanism is discussed.