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, cilt.56, ss.5386-5389, 2015 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 56 Konu: 40
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1016/j.tetlet.2015.07.090
  • Dergi Adı: TETRAHEDRON LETTERS
  • Sayfa Sayıları: ss.5386-5389

Özet

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.