Synthesis of thio- and furan-fused heterocycles: furopyranone, furopyrrolone, and thienopyrrolone derivatives

ERGUN M., DENGİZ Ç., OZER M. S., ŞAHİN E., BALCI M.

TETRAHEDRON, vol.70, no.35, pp.5993-5998, 2014 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 70 Issue: 35
  • Publication Date: 2014
  • Doi Number: 10.1016/j.tet.2014.05.071
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.5993-5998
  • Keywords: Acyl azide, Furopyranone, Furopyrrolone, Thienopyrrolone, Curtius rearrangement, IN-VITRO, CONSTRUCTION, THIOPHENE
  • Middle East Technical University Affiliated: Yes

Abstract

We report herein the synthesis of a novel class of compounds, ethyl 4-oxo-4H-furo[3,2-c]pyran-6-yl carbonate, (7E)-7-[(dimethylamino)methylene]-4H-furo[3,2-c]pyran-4,6(7H)-dione, 5-oxo-N-phenyl-2,5-dihydro-4H-furo[3,2-b]pyrrole-4-carboxamide,and 5-oxo-N-phenyl-5,6-dihydro-4H-thieno[3,2-b] pyrrole-4-carboxamide starting from the corresponding acid derivatives. Intramolecular cyclization in the presence of thionyl chloride formed the target fused ring systems. Additional transformation was seen in the cyclization of furan-fused heterocycle. A mechanism was proposed based on experimental and computational findings. (C) 2014 Elsevier Ltd. All rights reserved.