Synthesis of substituted quinolines by electrophilic cyclization of N-(2-alkynyl)anilines

被引：217

作者：

Zhang, XX ^{[1
]}

Campo, MA ^{[1
]}

Yao, TL ^{[1
]}

Larock, RC ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 05期

关键词：

D O I：

10.1021/ol0476218

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Quinolines substituted in the 3-position by an iodo or phenylseleno group are readily prepared in good to excellent yields by the reaction of propargylic anilines with appropriate electrophiles under mild reaction conditions.

引用

页码：763 / 766

页数：4

共 32 条

[1] Electrophilic cyclization of o-acetoxy- and o-benzyloxyalkynylpyridines:: An easy entry into 2,3-disubstituted furopyridines [J].

Arcadi, A ;

Cacchi, S ;

Di Giuseppe, S ;

Fabrizi, G ;

Marinelli, F .

ORGANIC LETTERS, 2002, 4 (14) :2409-2412

[2] 3-HALOQUINOLINES WITH SUBSTITUENTS IN THE 6-POSITIONS AND 8-POSITIONS [J].

BAKER, RH ;

TINSLEY, SW ;

BUTLER, D ;

RIEGEL, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (01) :393-395

[3]

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

[4] IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes:: Direct assembly of 3-iodoindole cores [J].

Barluenga, J ;

Trincado, M ;

Rubio, E ;

González, JM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (21) :2406-2409

[5] Cyclization of carbonyl groups onto alkynes upon reaction with IPy2BF4 and their trapping with nucleophiles:: A versatile trigger for assembling oxygen heterocycles [J].

Barluenga, J ;

Vázquez-Villa, H ;

Ballesteros, A ;

González, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (30) :9028-9029

[6] Regioselective synthesis of substituted naphthalenes:: A novel de novo approach based on a metal-free protocol for stepwise cycloaddition of o-alkynylbenzaldehyde derivatives with either alkynes or alkenes [J].

Barluenga, J ;

Váquez-Villa, H ;

Ballesteros, A ;

González, JM .

ORGANIC LETTERS, 2003, 5 (22) :4121-4123

[7] IODINE-INDUCED STEREOSELECTIVE CARBOCYCLIZATIONS - A NEW METHOD FOR THE SYNTHESIS OF CYCLOHEXANE AND CYCLOHEXENE DERIVATIVES [J].

BARLUENGA, J ;

GONZALEZ, JM ;

CAMPOS, PJ ;

ASENSIO, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (11) :1546-1547

[8]

BARREAU M, 1987, SYNTHESIS-STUTTGART, P262

[9] Preparation of 3-haloquinolines from 3-amino-2-halo-2-alkenimines [J].

Campos, PJ ;

Tan, CQ ;

Rodriguez, MA ;

Anon, E .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) :7195-7197

[10] Diphenyl quinolines and isoquinolines: Synthesis and primary biological evaluation [J].

Croisy-Delcey, M ;

Croisy, A ;

Carrez, D ;

Huel, C ;

Chiaroni, A ;

Ducrot, P ;

Bisagni, E ;

Jin, L ;

Leclercq, G .

BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (11) :2629-2641

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