Copper-Catalyzed One-Pot Synthesis of 3-(N-Heteroarenyl)acrylonitriles through Radical Conjugated Addition of β-Nitrostyrene to Methylazaarenes

被引：6

作者：

Moreira, Natalia M. ^{[1
]}

Martelli, Lorena S. R. ^{[1
]}

de Julio, Kiyara I. R. ^{[1
]}

Zukerman-Schpector, Julio ^{[2
]}

Opatz, Till ^{[3
]}

Correa, Arlene G. ^{[1
]}

机构：

[1] Univ Fed Sao Carlos, Ctr Excellence Res Sustainable Chem, BR-13565905 Sao Carlos, SP, Brazil

[2] Univ Fed Sao Carlos, Chem Dept, BR-13565905 Sao Carlos, SP, Brazil

[3] Johannes Gutenberg Univ Mainz, Dept Chem, Duesbergweg 10-14, D-55128 Mainz, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 29期

基金：

巴西圣保罗研究基金会;

关键词：

C-H activation; Copper; Nitrogen heterocycles; Radical reactions; Synthetic methods; C-H FUNCTIONALIZATION; 1,4-ADDITION; ALKYLATION; AZAARENES; TRENDS;

D O I：

10.1002/ejoc.202000673

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple procedure for the copper-catalyzed synthesis of 3-(N-heteroaryl)acrylonitriles was developed. Using a combination of Lewis and Bronsted acids, this one-pot procedure undergoes via a radical conjugated addition and dehydration processes, without isolation of any intermediate, affording the acrylonitriles. This diastereoselective approach allowed the synthesis of a broad scope of quinazoline derivatives (22 examples) with moderate to good yields and good functional-group tolerance and could be extended to otherN-heterocyles such as quinolines and isoquinolines. Based on control experiments, a mechanistic proposal for this new transformation is also presented.

引用

页码：4563 / 4570

页数：8

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