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

Date

2014-09-02

Author

ERGUN, Merve
Dengiz, Çağatay
OZER, Merve Sinem
ŞAHİN, Ertan
BALCI, METİN

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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.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/42686

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2014.05.071

Collections

Department of Chemistry, Article

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Citation Formats

M. ERGUN, Ç. Dengiz, M. S. OZER, E. ŞAHİN, and M. BALCI, “Synthesis of thio- and furan-fused heterocycles: furopyranone, furopyrrolone, and thienopyrrolone derivatives,” TETRAHEDRON, pp. 5993–5998, 2014, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/42686.