Iodothiophenes and Related Compounds as Coupling Partners in Copper-Mediated N-Arylation of Anilines,Synthesis

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Iodothiophenes and Related Compounds as Coupling Partners in Copper-Mediated N-Arylation of Anilines
Synthesis ( IF 2.2 ) Pub Date : 2020-10-26 , DOI: 10.1055/s-0040-1706542
Ghenia Bentabed-Ababsa ₁ , Laurent Picot ₂ , Florence Mongin ₃ , Salima Bouarfa _{1,

3} , William Erb ₃ , Valérie Thiéry ₂ , Thierry Roisnel ₃ , Vincent Dorcet ₃

Affiliation

Abstract

N-Arylation of various 2-acylated anilines with different electron-rich heteroaryl iodides (2- and 3-iodothiophenes, 2- and 3-iodobenzothiophenes, 2-iodobenzofuran) was achieved by using activated copper and potassium carbonate in dibutyl ether at reflux. The reactivity of the different heteroaryl iodides and anilines employed was discussed and rationalized on the basis of their electronic features. Subsequent cyclization by aromatic electrophilic substitution easily took place in the case of C2-free (benzo)thienyl or C3-free (benzo)furyl derivatives, affording original tri- and tetracycles. The antiproliferative activity of most of them was evaluated in A2058 melanoma cells and revealed four chlorinated tetracycles as effective growth inhibitors.

Publication History

Received: 12 August 2020

Accepted after revision: 18 September 2020

Publication Date:
26 October 2020 (online)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

中文翻译：

碘噻吩及其相关化合物在铜介导的苯胺N-化中的偶联伙伴

摘要

Ñ各种-Arylation 2酰化具有不同的富电子杂芳基碘化物（2-和3- iodothiophenes，2-和3- iodobenzothiophenes，2-碘苯并呋喃）苯胺通过使用活化的铜和碳酸钾在二丁基醚在回流下实现。根据不同的电子特性，对所使用的不同杂芳基碘化物和苯胺的反应性进行了讨论和合理化。在不含C 2（苯并）噻吩基或不含C 3（苯并呋喃基）的衍生物的情况下，随后通过芳族亲电子取代容易进行环化，得到原始的三环和四环。在A2058黑色素瘤细胞中评估了其中大多数的抗增殖活性，并揭示了四个氯化四环作为有效的生长抑制剂。