First radical addition onto ketenimines: a novel synthesis of indoles

被引：43

作者：

Alajarin, M ^{[1
]}

Vidal, A ^{[1
]}

Ortin, MM ^{[1
]}

机构：

[1] Univ Murcia, Fac Quim, Dept Quim Organ, E-30071 Murcia, Spain

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 15期

关键词：

cyclization; indoles; ketenimines; radical reactions;

D O I：

10.1016/S0040-4039(03)00562-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel radical-mediated synthesis of 2-alkyl indoles is described. The method is a nonchain process based on the intramolecular addition of benzylic radicals onto the central carbon atom of a ketenimine function, resulting in a 5-exo-dig cyclization. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：3027 / 3030

页数：4

相关论文

共 52 条

[1] Intramolecular [4+2] cycloaddition reactions of ketenimines:: A new synthesis of benz[b]acridines [J].

Alajarín, M ;

Vidal, A ;

Ortín, MM ;

Tovar, F .

SYNTHESIS-STUTTGART, 2002, (16) :2393-2398

[2] Highly stereocontrolled [2+2] cycloaddition versus unprecedented imino-ene reactions of imino-ketenimines [J].

Alajarín, M ;

Vidal, A ;

Tovar, F ;

Sánchez-Andrada, P .

TETRAHEDRON LETTERS, 2002, 43 (35) :6259-6261

[3]

Alajarín M, 1998, CHEM-EUR J, V4, P2558

[4] New stereoselective intramolecular [2+2] cycloadditions between ketenimines and imines on an ortho-benzylic scaffold:: 1,4-asymmetric induction [J].

Alajarín, M ;

Vidal, A ;

Tovar, F ;

de Arellano, MCR ;

Cossío, FP ;

Arrieta, A ;

Lecea, B .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (22) :7512-7515

[5] Intramolecular [2+2] cycloaddition of ketenimines with imines [J].

Alajarin, M ;

Molina, P ;

Vidal, A .

TETRAHEDRON LETTERS, 1996, 37 (49) :8945-8948

[6] Formal [4+2] intramolecular cycloaddition ketenimine-imine.: Synthesis of benzimidazo[1,2-b]isoquinolines [J].

Alajarín, M ;

Vidal, A ;

Tovar, F ;

Conesa, C .

TETRAHEDRON LETTERS, 1999, 40 (33) :6127-6130

[7] Intramolecular [2+2] cycloaddition of ketenimines with imines. Synthesis and chemical behaviour of azeto[2,1-b]quinazolines [J].

Alajarin, M ;

Molina, P ;

Vidal, A ;

Tovar, F .

TETRAHEDRON, 1997, 53 (39) :13449-13472

[8] Periselective intramolecular [4+2] cycloadditions of ketenimines:: synthesis of pyrido[1,2-a]benzimidazoles [J].

Alajarín, M ;

Vidal, A ;

Tovar, F .

TETRAHEDRON LETTERS, 2000, 41 (36) :7029-7032

[9]

Alajarín M, 1999, CHEM-EUR J, V5, P1106, DOI 10.1002/(SICI)1521-3765(19990301)5:3<1106::AID-CHEM1106>3.3.CO

[10]

2-9

← 1 2 3 4 5 6 →