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Reaction between Furan‐ or Thiophene‐2‐carbonyl Chloride, Isocyanides, and Dialkyl Acetylenedicarboxylates: Multicomponent Synthesis of 2,2′‐Bifurans and 2‐(Thiophen‐2‐yl)furans
Author(s) -
Sayahi Mohammad Hosein,
Adib Mehdi,
Hamooleh Zeinab,
Zhu LongGuan,
Amanlou Massoud
Publication year - 2015
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201500005
Subject(s) - furan , chemistry , thiophene , isocyanide , electrophile , medicinal chemistry , electrophilic substitution , derivative (finance) , organic chemistry , catalysis , financial economics , economics
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 CH 2 Cl 2 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.