Selenium‐Mediated Cyclization Reaction of 2‐Vinylanilines with/without Isonitriles: Efficient Synthesis of 2‐Aminoquinoline/ 3‐Aryl‐1H‐indole Derivatives,Asian Journal of Organic Chemistry

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Selenium‐Mediated Cyclization Reaction of 2‐Vinylanilines with/without Isonitriles: Efficient Synthesis of 2‐Aminoquinoline/ 3‐Aryl‐1H‐indole Derivatives
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2020-03-17 , DOI: 10.1002/ajoc.202000119
Xi Zhang ₁ , Yong‐Qing Wang ₁ , Anwar L. Alduma ₁ , Ullah Arif S. H ₁ , Xi‐Cun Wang ₁ , Zheng‐Jun Quan ₁

Affiliation

Herein, we report a non‐metal strategy for cyclization reactions of 2‐vinylanilines with/without isonitriles to synthesize 2‐aminoquinoline and 3‐aryl‐1H‐indole derivatives. A series of 2‐aminoquinolines were afforded in good to excellent yields in a direct, facile, and efficient approach by Se‐catalyzed isocyanide insertion with 2‐vinylanilines under an air atmosphere. This reaction not only used low toxicity Se as the catalyst, isocyanobenzene substrates were compatible too compared to previous report. Meanwhile, an intramolecular cyclization of 2‐vinylanilines was developed to give 3‐aryl‐1H‐indoles in moderate to good yields by using SeO₂ as oxidant.

中文翻译：

硒介导的2-乙烯基苯胺与/不具有异腈的环化反应：2-氨基喹啉/ 3-芳基-1H-吲哚衍生物的高效合成

本文中，我们报告了一种非金属策略，用于2-乙烯基苯胺与/不具有异腈的环化反应，以合成2-氨基喹啉和3-芳基-1 H-吲哚衍生物。通过在空气气氛下通过Se催化异氰酸酯与2-乙烯基苯胺的直接插入，简便而有效的方法，获得了一系列2-氨基喹啉，具有良好或优异的收率。该反应不仅使用低毒性的硒作为催化剂，而且与以前的报道相比，异氰基苯的底物也是相容的。同时，通过使用SeO ₂作为氧化剂，开发了2-乙烯基苯胺的分子内环化反应，以中等至良好的产率获得了3-芳基-1 H-吲哚。

更新日期：2020-04-21

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