Green and Regioselective Alkylation of Dihydropyrimidinthiones through Michael Addition

Yaghoubi F., Imanzadeh G., Asgharzadeh R., Soltanzadeh Z., Öztürk T.

Letters in Organic Chemistry, vol.20, no.12, pp.1159-1169, 2023 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 20 Issue: 12
  • Publication Date: 2023
  • Doi Number: 10.2174/1570178620666230622115431
  • Journal Name: Letters in Organic Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core
  • Page Numbers: pp.1159-1169
  • Keywords: aza-michael addition, Dihydropyrimidin-2(1H)-thiones, green conditions, high regioselective synthesis, sulfur-containing com-pounds, tetrabutylammonium bromide
  • Istanbul Technical University Affiliated: Yes


Dihydropyrimidines are one of the most important heterocyclic ring systems having a serious place in medicinal and organic synthesis. In this paper, a new series of dihydropyrimidines consisting of sulfur atoms were synthesized using inorganic base K2CO3 and TBAB as an organic salt to make high polarity in reaction media. Interestingly, different 3,4-dihydropyrimidin-2(1H)-thiones re-acted smoothly with various acrylic esters to afford adducts via highly regioselective N3-Michael addition reaction was carried out at 100oC in 12 h. result: Unfortunately, the reaction failed with fumaric esters owing steric effects. Avoiding organic solvents during this reaction effectively led to the development of an economic approach. Structures of the new compounds were established on the basis of1H NMR,13C NMR, and IR spectral data.