M. Sayahi, M. Adib, Zeinab Hamooleh
Sep 1, 2015
Citations
0
Influential Citations
8
Citations
Journal
Helvetica Chimica Acta
Abstract
An efficient multi-component synthesis of highly functionalized 2,2′-bifurans and 2-(thiophen-2-yl)furans is described. A mixture of furan- or thiophene-2-carbonyl chloride, an isocyanide, and a dialkyl acetylenedicarboxylate undergoes a smooth addition reaction in dry CH2Cl2 at ambient temperature to produce 2-amino-5-(4-chlorofuran-2-yl)furan-3,4-dicarboxylates and 2-amino-5-(4-chlorothiophen-2-yl)furan-3,4-dicarboxylates. A single-crystal X-ray-analysis of a derivative conclusively confirms the structure of these 2,2′-bifurans and 2-(thiophen-2-yl)furans. A novel electrophilic aromatic substitution reaction can justify the formation of the Cl-substituted furan or thiophene rings.