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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
Helvetica Chimica Acta ( IF 1.5 ) Pub Date : 2015-09-13 , DOI: 10.1002/hlca.201500005
Mohammad Hosein Sayahi , Mehdi Adib , Zeinab Hamooleh , Long-Guan Zhu , Massoud Amanlou

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.

中文翻译:

呋喃或噻吩-2-羰基氯化物,异氰酸酯和乙炔二羧酸二烷基酯之间的反应:2,2'-呋喃和2-(噻吩-2-基)呋喃的多组分合成

描述了高度官能化的2,2'-呋喃和2-(噻吩-2-基)呋喃的高效多组分合成方法。呋喃或噻吩-2-碳酰氯,异氰化物和乙酰二羧酸二烷基酯的混合物在室温下于干燥的CH 2 Cl 2中进行平稳加成反应,生成2-氨基-5-(4-氯呋喃-2-烷基)呋喃-3,4-二羧酸酯和2-氨基-5-(4-氯噻吩-2-基)呋喃-3,4-二羧酸酯。衍生物的单晶X射线分析最终确定了这些2,2'-呋喃和2-(噻吩-2-基)呋喃的结构。一种新颖的亲电子芳族取代反应可以证明形成Cl取代的呋喃或噻吩环。
更新日期:2015-09-13
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