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

收藏

页码：696 / 703

页数：8

相关论文

共 55 条

[1] 3-Substituted-N-(4-Hydroxynaphthalen-1-yl)arylsulfonamides as a Novel Class of Selective Mcl-1 Inhibitors: Structure-Based Design, Synthesis, SAR, and Biological Evaluation [J].

Abulwerdi, Fardokht A. ;

Liao, Chenzhong ;

Mady, Ahmed S. ;

Gavin, Jordan ;

Shen, Chenxi ;

Cierpicki, Tomasz ;

Stuckey, Jeanne A. ;

Showalter, H. D. Hollis ;

Nikoovska-Coleska, Zaneta .

JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (10) :4111-4133

[2] Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine [J].

Bae, I ;

Han, H ;

Chang, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) :2038-2039

[3] Palladium-catalyzed intermolecular coupling of aryl chlorides and sulfonamides under microwave irradiation [J].

Burton, G ;

Cao, P ;

Li, G ;

Rivero, R .

ORGANIC LETTERS, 2003, 5 (23) :4373-4376

[4] Sulfonamide derivatives with protease inhibitory action as anticancer, anti-inflammatory and antiviral agents [J].

Casini, A ;

Scozzafava, A ;

Supuran, CT .

EXPERT OPINION ON THERAPEUTIC PATENTS, 2002, 12 (09) :1307-1327

[5] Palladium-catalyzed ortho-alkenylation of aryl hydrogen phosphates using a new mono-phosphoric acid directing group [J].

Chan, Li Yan ;

Kim, Sunggak ;

Ryu, Taekyu ;

Lee, Phil Ho .

CHEMICAL COMMUNICATIONS, 2013, 49 (41) :4682-4684

[6] Room temperature copper-catalyzed 2-functionalization of pyrrole rings by a three-component coupling reaction [J].

Cho, Seung Hwan ;

Chang, Sukbok .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (15) :2836-2839

[7] Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water [J].

Cho, SH ;

Yoo, EJ ;

Bae, L ;

Chang, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) :16046-16047

[8] Stereoselective DABCO-Catalyzed Synthesis of (E)-α-Ethynyl-α,β-Unsaturated Esters from Allenyl Acetates [J].

Choe, Yongsik ;

Lee, Phil Ho .

ORGANIC LETTERS, 2009, 11 (06) :1445-1448

[9] Efficient synthesis of 2-imino-1,2-dihydroquinolines and 2-immothiochromenes via copper-catalyzed domino reaction [J].

Cui, Sun-Liang ;

Wang, Jing ;

Wang, Yan-Guang .

TETRAHEDRON, 2008, 64 (03) :487-492

[10] Synthesis and antimalarial activity of trioxaquine derivatives [J].

Dechy-Cabaret, O ;

Benoit-Vical, F ;

Loup, C ;

Robert, A ;

Gornitzka, H ;

Bonhoure, A ;

Vial, H ;

Magnaval, JF ;

Séguéla, JP ;

Meunier, B .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (07) :1625-1636

← 1 2 3 4 5 6 →