Pyridinium N-2'-pyridylaminide:: radical cyclization for the synthesis of benzonaphthyridine derivatives

被引：13
作者：
Nunez, Araceli [1 ]
Sanchez, Aranzazu [1 ]
Burgos, Carolina [1 ]
Alvarez-Builla, Julio [1 ]
机构：
[1] Univ Alcala de Henares, Dept Quim Organ, Madrid 28871, Spain
来源：
TETRAHEDRON | 2007年 / 63卷 / 29期
关键词：
D O I：
10.1016/j.tet.2007.04.077
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of benzonaphthyridine derivatives that incorporate a 2-aminopyridine moiety can be performed by intramolecular radical pyridylation of the appropriate substrates, obtained from pyridinium N-2'-pyridylaminide, using TTMSS and AIBN. similar to 2007 Elsevier Ltd. All rights reserved.
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收藏
页码：6774 / 6783
页数：10
相关论文
共 36 条
[1]   Aaptamine, a spongean alkaloid, activates p21 promoter in a p53-independent manner [J].
Aoki, S ;
Kong, DX ;
Suna, H ;
Sowa, Y ;
Sakai, T ;
Setiawan, A ;
Kobayashi, M .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2006, 342 (01) :101-106
[2]   Tin-free radical cyclizations for the synthesis of 7-azaoxindoles, 7-azaindolines, tetrahydro[1,8]naphthyridines, and tetrahydro-5H-pyrido[2,3-b]azepin-8-ones [J].
Bacqué, E ;
El Qacemi, M ;
Zard, SZ .
ORGANIC LETTERS, 2004, 6 (21) :3671-3674
[3]   Selective urokinase-type plasminogen activator (uPA) inhibitors. Part 2: (3-Substituted-5-halo-2-pyridinyl)guanidines [J].
Barber, CG ;
Dickinson, RP .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (02) :185-187
[4]   HALOGENATION OF PYRIDINIUM-N-(2'-PYRIDYL)AMINIDE - AN EASY SYNTHESIS OF HALO-2-AMINOPYRIDINES [J].
BURGOS, C ;
DELGADO, F ;
GARCIANAVIO, JL ;
IZQUIERDO, ML ;
ALVAREZBUILLA, J .
TETRAHEDRON, 1995, 51 (31) :8649-8654
[5]   A new, direct, and efficient synthesis of benzonaphthyridin-5-ones [J].
Cailly, Thomas ;
Fabis, Frederic ;
Rault, Sylvain .
TETRAHEDRON, 2006, 62 (25) :5862-5867
[6]   PYRIDINIUM-N-(2-PYRIDYL)AMINIDES - A SELECTIVE APPROACH TO SUBSTITUTED 2-AMINOPYRIDINES [J].
CARCELLER, R ;
GARCIANAVIO, JL ;
IZQUIERDO, ML ;
ALVAREZBUILLA, J .
TETRAHEDRON LETTERS, 1993, 34 (12) :2019-2020
[7]   N-azinylpyridinium N-aminides:: tandem reactions with α-halocarbonyl derivatives and analogs [J].
de la Rosa, R ;
Martínez-Barrasa, V ;
Burgos, C ;
Alvarez-Builla, J .
TETRAHEDRON LETTERS, 2000, 41 (31) :5837-5840
[8]   Radical cyclization approach to spirocyclohexadienones [J].
de Turiso, FGL ;
Curran, DP .
ORGANIC LETTERS, 2005, 7 (01) :151-154
[9]  
de Viedma AG, 1999, J ORG CHEM, V64, P1007
[10]   An unprecedented radical ring closure on a pyridine nitrogen [J].
El Qacemi, Myriem ;
Ricard, Louis ;
Zard, Samir Z. .
CHEMICAL COMMUNICATIONS, 2006, (42) :4422-4424
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