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

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

TETRAHEDRON LETTERS, vol.56, pp.5386-5389, 2015 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 56
  • Publication Date: 2015
  • Doi Number: 10.1016/j.tetlet.2015.07.090
  • Journal Name: TETRAHEDRON LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.5386-5389
  • Keywords: Alkynes, Cyclization, Alkynones, 2-Mercaptoacetaldehyde, 2,3-Disubstituted thiophenes, ONE-POT SYNTHESIS, FACILE SYNTHESIS, SUBSTITUTED THIOPHENES, HIGH-EFFICIENCY, ORGANIC-DYES, DERIVATIVES, LORNOXICAM, ANNULATION, POLYMERS, FURANS
  • Bursa Uludag University Affiliated: No

Abstract

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.