Au-Catalyzed Formation of Functionalized Quinolines from 2-Alkynyl Arylazide Derivatives

被引：103

作者：

Gronnier, Colombe ^{[1
]}

Boissonnat, Guillaume ^{[1
]}

Gagosz, Fabien ^{[1
]}

机构：

[1] Ecole Polytech, CNRS, Lab Synth Organ, UMR 7652, F-91128 Palaiseau, France

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 16期

关键词：

GOLD; CYCLIZATION; 1,2-DIHYDROQUINOLINES; EFFICIENT;

D O I：

10.1021/ol4019634

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for converting 2-alkynyl arylazide derivatives into functionalized polysubstituted quinolines following a gold-catalyzed 1,3-acetoxy shift/cyclization/1,2-group shift sequence has been developed. This transformation proceeds under mild reaction conditions, is efficient, and tolerates a large variety of functional groups.

引用

页码：4234 / 4237

页数：4

共 25 条

[1]

Balasubramanian M., 1996, COMPREHENSIVE HETERO, V5, P245, DOI 10.1016/B978-008096518-5.00109

[2]

Benitez D, 2009, NAT CHEM, V1, P482, DOI [10.1038/NCHEM.331, 10.1038/nchem.331]

[3] Gold and Bronsted Acid Catalyzed Hydride Shift onto Allenes: Divergence in Product Selectivity [J].

Bolte, Benoit ;

Gagosz, Fabien .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (20) :7696-7699

[4] Gold-Catalyzed Tandem Cycloisomerization/Cope Rearrangement: An Efficient Access to the Hydroazulenic Motif [J].

Cao, Ziping ;

Gagosz, Fabien .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (34) :9014-9018

[5]

Eicher T., 2003, The Chemistry of Heterocycles, P52, DOI [10.1002/352760183X.ch5a, DOI 10.1002/352760183X]

[6] Allenyl azide cycloaddition chemistry. Synthesis of annelated indoles from 2-(allenyl)phenyl azide substrates [J].

Feldman, Ken S. ;

Iyer, Malliga R. ;

Hester, D. Keith, II .

ORGANIC LETTERS, 2006, 8 (14) :3113-3116

[7] Allenyl Azide Cycloaddition Chemistry. 2,3-Cyclopentennelated Indole Synthesis through Indolidene Intermediates [J].

Feldman, Ken S. ;

Hester, D. Keith, II ;

Iyer, Malliga R. ;

Munson, Paul J. ;

Silva Lopez, Carlos ;

Nieto Faza, Olalla .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (14) :4958-4974

[8] Gold(I)-catalyzed intramolecular acetylenic Schmidt reaction [J].

Gorin, DJ ;

Davis, NR ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (32) :11260-11261

[9] Gold(I)-catalyzed formation of dihydroquinolines and indoles from N-aminophenyl propargyl malonates [J].

Gronnier, Colombe ;

Odabachian, Yann ;

Gagosz, Fabien .

CHEMICAL COMMUNICATIONS, 2011, 47 (01) :218-220

[10]

Hashmi A. S. K., 2009, TETRAHEDRON, V65, P1919

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