Copper(I)-catalyzed Cyclization Reactions of Ethyl (E)-α-Ethynyl-β-Aryl-α,β-Unsaturated Esters with N-Sulfonyl Azides: Synthesis of 1-Aminonaphthalene, 3-Aminobenzofuran, and 3-Aminothiobenzofuran Derivatives

被引：3

作者：

Son, Jeong-Yu ^{[1
]}

Han, Gi Uk ^{[1
]}

Ko, Gi Hoon ^{[1
]}

Maeng, Chanyoung ^{[1
]}

Shin, Seohyun ^{[1
]}

Lee, Phil Ho ^{[1
]}

机构：

[1] Kangwon Natl Univ, Dept Chem, Chunchon 24341, South Korea

来源：

BULLETIN OF THE KOREAN CHEMICAL SOCIETY | 2019年 / 40卷 / 07期

基金：

新加坡国家研究基金会;

关键词：

Aminonaphthalene; Dipolar cycloaddition; Ketenimine; Cyclization; Copper; ONE-POT SYNTHESIS; SULFONAMIDE DERIVATIVES; EFFICIENT SYNTHESIS; CASCADE REACTIONS; INHIBITORS; 4-AMINOQUINOLINES; AMINATION; DISCOVERY; ALKYNES; ROUTE;

D O I：

10.1002/bkcs.11755

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A synthetic method for ethyl 4-(alkyl or arylsulfonamido)-2-naphthoates from ethyl (E)-alpha-ethynyl-beta-aryl-alpha,beta-unsaturated esters (1) and N-sulfonyl azides (2) in the presence of 2,6-lutidine in THF at 60 degrees C for 3 h was developed in one step, in which a copper(I)-catalyzed 1,3-dipolar cycloaddition, ketenimine formation, and 6 pi-electrocyclization followed by [1,3]-H shift tandem reaction took place. This method enabled efficient synthesis of a wide range of 1-aminonaphthalene and 3-aminobenzofuran and 3-aminobenzothiophene derivatives with the release of molecular nitrogen.

引用

页码：696 / 703

页数：8

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