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

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

Show Affiliations

1. Department of Chemistry, Payame Noor University (PNU), P.O. Box 19395, Tehran, 3697, Iran
2. School of Chemistry, College of Science, University of Tehran, P.O. Box 14155-6455, Tehran, Iran
3. Chemistry Department, Zhejiang University, Hangzhou, 310027, China
4. Pharmaceutical Sciences Research Center, Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

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.

Style	Citing Format
MLA	Sayahi MH, et al.. "Reaction Between Furan- or Thiophene-2-Carbonyl Chloride, Isocyanides, and Dialkyl Acetylenedicarboxylates: Multicomponent Synthesis of 2,2′-Bifurans and 2-(Thiophen-2-Yl)Furans." Helvetica Chimica Acta, vol. 98, no. 9, 2015, pp. 1231-1239.
APA	Sayahi MH, Adib M, Hamooleh Z, Zhu LG, Amanlou M (2015). Reaction Between Furan- or Thiophene-2-Carbonyl Chloride, Isocyanides, and Dialkyl Acetylenedicarboxylates: Multicomponent Synthesis of 2,2′-Bifurans and 2-(Thiophen-2-Yl)Furans. Helvetica Chimica Acta, 98(9), 1231-1239.
Chicago	Sayahi MH, Adib M, Hamooleh Z, Zhu LG, Amanlou M. "Reaction Between Furan- or Thiophene-2-Carbonyl Chloride, Isocyanides, and Dialkyl Acetylenedicarboxylates: Multicomponent Synthesis of 2,2′-Bifurans and 2-(Thiophen-2-Yl)Furans." Helvetica Chimica Acta 98, no. 9 (2015): 1231-1239.
Harvard	Sayahi MH et al. (2015) 'Reaction Between Furan- or Thiophene-2-Carbonyl Chloride, Isocyanides, and Dialkyl Acetylenedicarboxylates: Multicomponent Synthesis of 2,2′-Bifurans and 2-(Thiophen-2-Yl)Furans', Helvetica Chimica Acta, 98(9), pp. 1231-1239.
Vancouver	Sayahi MH, Adib M, Hamooleh Z, Zhu LG, Amanlou M. Reaction Between Furan- or Thiophene-2-Carbonyl Chloride, Isocyanides, and Dialkyl Acetylenedicarboxylates: Multicomponent Synthesis of 2,2′-Bifurans and 2-(Thiophen-2-Yl)Furans. Helvetica Chimica Acta. 2015;98(9):1231-1239.
BibTex	@article{ author = {Sayahi MH and Adib M and Hamooleh Z and Zhu LG and Amanlou M}, title = {Reaction Between Furan- or Thiophene-2-Carbonyl Chloride, Isocyanides, and Dialkyl Acetylenedicarboxylates: Multicomponent Synthesis of 2,2′-Bifurans and 2-(Thiophen-2-Yl)Furans}, journal = {Helvetica Chimica Acta}, volume = {98}, number = {9}, pages = {1231-1239}, year = {2015} }
RIS	TY - JOUR AU - Sayahi MH AU - Adib M AU - Hamooleh Z AU - Zhu LG AU - Amanlou M TI - Reaction Between Furan- or Thiophene-2-Carbonyl Chloride, Isocyanides, and Dialkyl Acetylenedicarboxylates: Multicomponent Synthesis of 2,2′-Bifurans and 2-(Thiophen-2-Yl)Furans JO - Helvetica Chimica Acta VL - 98 IS - 9 SP - 1231 EP - 1239 PY - 2015 ER -

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