Intermolecular heterocyclization of alkynones with 2-mercaptoacetaldehyde under metal-free conditions: synthesis of 2,3-disubstituted thiophenes

Vatansever E. C., Kilic K., Ozer M. S., Koza G., Menges N., Balci M.

TETRAHEDRON LETTERS, vol.56, no.40, pp.5386-5389, 2015 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 56 Issue: 40
  • Publication Date: 2015
  • Doi Number: 10.1016/j.tetlet.2015.07.090
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.5386-5389
  • Van Yüzüncü Yıl University Affiliated: Yes


A concise and regioselective approach for the synthesis of 2,3-disubstituted thiophene derivatives has been developed. The synthetic strategy relies on the reaction of an in situ generated 2-mercaptoacetaldehyde with various alkynones. Furthermore, we calculated the energy gap between the HOMO and the LUMO orbitals of all compounds and observed that the introduction of a strong electron-withdrawing group decreased the HOMO-LUMO energy gap. (C) 2015 Elsevier Ltd. All rights reserved.