Copper-catalyzed cyclization of 2-cyanobenzaldehydes and 2-isocyanoacetates: an efficient strategy for the synthesis of substituted 1-aminoisoquinolines

被引：14

作者：

Bao, Wen ^{[1
]}

Wang, Jun-Qi ^{[1
]}

Xu, Xue-Tao ^{[2
]}

Zhang, Bang-Hong ^{[1
]}

Liu, Wei-Ting ^{[1
]}

Lei, Lin-Sheng ^{[1
]}

Liang, Huan ^{[1
]}

Zhang, Kun ^{[2
]}

Wang, Shao-Hua ^{[1
,2
,3
]}

机构：

[1] Lanzhou Univ, Sch Pharm, Lanzhou 730000, Gansu, Peoples R China

[2] Wuyi Univ, Sch Chem & Environm Engn, Jiangmen 529020, Peoples R China

[3] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 59期

基金：

中国国家自然科学基金;

关键词：

ELECTROCYCLIC RING-CLOSURE; C BOND FORMATION; ISOCYANIDE INSERTION; ISOQUINOLINE ALKALOIDS; PHENANTHRIDINE DERIVATIVES; NITROGEN-HETEROCYCLES; ARYL BROMIDES; H ACTIVATION; CASCADE; CHEMISTRY;

D O I：

10.1039/c8cc04733b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Cu(acac)(2)-catalyzed cyclization reaction of 2-cyanobenzaldehydes with 2-isocyanoacetates has been successfully developed providing an efficient strategy for the synthesis of substituted 1-aminoisoquinolines. The reaction proceeds smoothly under mild conditions with high efficiency, and might provide an alternative strategy for the synthesis of 1-aminoisoquinoline containing molecules.

引用

页码：8194 / 8197

页数：4

共 73 条

[1] retro-Cheletropic ene reactions with 2-carbena-1,3-dioxolane as chelefuge [J].

Alajarin, Mateo ;

Marin-Luna, Marta ;

Ortin, Maria-Mar ;

Sanchez-Andrada, Pilar ;

Vidal, Angel .

TETRAHEDRON, 2011, 67 (31) :5590-5595

[2]

Bentley K. W., 1971, ALKALOIDS, V1, P106

[3] Cyclic sulfamidates as versatile lactam precursors. An evaluation of synthetic strategies towards (-)-aphanorphine [J].

Bower, John F. ;

Szeto, Peter ;

Gallagher, Timothy .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (01) :143-150

[4] Assembly of indole-2-carboxylic acid esters through a ligand-free copper-catalysed cascade process [J].

Cai, Qian ;

Li, Zhengqiu ;

Wei, Jiajia ;

Ha, Chengyong ;

Pei, Duanqing ;

Ding, Ke .

CHEMICAL COMMUNICATIONS, 2009, (48) :7581-7583

[5] New highlights in the synthesis and reactivity of 1,4-dihydropyrazine derivatives [J].

Chaignaud, Mathilde ;

Gillaizeau, Isabelle ;

Ouhamou, Nouara ;

Coudert, Gerard .

TETRAHEDRON, 2008, 64 (35) :8059-8066

[6] Easily accessible benzamide-derived P,O ligands (Bphos) for palladium-catalyzed carbon-nitrogen bond-forming reactions [J].

Chen, Guoshu ;

Lam, Wai Har ;

Fok, Wai Shan ;

Lee, Hang Wai ;

Kwong, Fuk Yee .

CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (02) :306-313

[7] Access to novel bicyclic fused γ-butyrolactone using [3,3]-sigmatropic rearrangement and acid-lactonization sequence as key transformation [J].

Claveau, Elise ;

Noirjean, Erwan ;

Bouyssou, Pascal ;

Coudert, Gerard ;

Gillaizeau, Isabelle .

TETRAHEDRON LETTERS, 2010, 51 (23) :3130-3133

[8]

Dale Boger L., 1984, TETRAHEDRON LETT, V25, P3175

[9] Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].

Dömling, A .

CHEMICAL REVIEWS, 2006, 106 (01) :17-89

[10]

Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO

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