Reaction Between Furan- or Thiophene-2-Carbonyl Chloride, Isocyanides, and Dialkyl Acetylenedicarboxylates: Multicomponent Synthesis of 2,2′-Bifurans and 2-(Thiophen-2-Yl)Furans Publisher



Sayahi MH¹ ; Adib M² ; Hamooleh Z¹ ; Zhu LG³ ; Amanlou M⁴
Source: Helvetica Chimica Acta Published:2015

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. Copyright © 2015 Verlag Helvetica Chimica Acta AG, Zurich.