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

被引:88
作者
Bacqué, E
El Qacemi, M
Zard, SZ [1 ]
机构
[1] Ecole Polytech, CNRS, Organ Synth Lab, F-91128 Palaiseau, France
[2] AVENTIS Pharma, F-94400 Vitry Sur Seine, France
关键词
D O I
10.1021/ol0489649
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Compounds containing a pyridine nucleus fused to a saturated nitrogen-containing ring, including 7-azaoxindoles, 7-azaindolines, tetrahydro-[1,8]naphthyridines, and tetrahydro-5H-pyrido[2,3-b]azepin-8-ones, were prepared in good yield starting from various 2,6-dichloropyridines. The method hinges on a free-radical xanthate-mediated cyclization or intermolecular addition/cyclization sequence for the construction of the new fused rings.
引用
收藏
页码:3671 / 3674
页数:4
相关论文
共 31 条
[1]   5,6,7,8-TETRAHYDROQUINOLINES .5. ANTIULCER AND ANTISECRETORY ACTIVITY OF 5,6,7,8-TETRAHYDROQUINOLINETHIOUREAS AND RELATED HETEROCYCLES [J].
BEATTIE, DE ;
CROSSLEY, R ;
CURRAN, ACW ;
HILL, DG ;
LAWRENCE, AE .
JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (05) :718-721
[2]  
BERGEOT O, UNPUB
[3]  
CHENG CC, 1982, ORG REACTIONS, V28, P37
[4]   Synthesis of 5-substituted 7-azaoxindoles via palladium-catalyzed reactions [J].
Cheung, M ;
Hunter, RN ;
Peel, MR ;
Lackey, KE .
HETEROCYCLES, 2001, 55 (08) :1583-1590
[5]   3-[(2-methyl-1,3-thiazol-4-yl)ethynyl]-pyridine: A potent and highly selective metabotropic glutamate subtype 5 receptor antagonist with anxiolytic activity [J].
Cosford, NDP ;
Tehrani, L ;
Roppe, J ;
Schweiger, E ;
Smith, ND ;
Anderson, J ;
Bristow, L ;
Brodkin, J ;
Jiang, XH ;
McDonald, I ;
Rao, S ;
Washburn, M ;
Varney, MA .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (02) :204-206
[6]   An efficient one-pot synthesis of annulated pyridines utilising a directed ortho-metallation/transmetallation approach [J].
Davies, AJ ;
Brands, KMJ ;
Cowden, CJ ;
Dolling, UH ;
Lieberman, DR .
TETRAHEDRON LETTERS, 2004, 45 (08) :1721-1724
[7]   Palladium heteroannulation process for synthesis of substituted pyrrolo [2,3-b]pyridin-3-ones [J].
Desarbre, E ;
Merour, JY .
TETRAHEDRON LETTERS, 1996, 37 (01) :43-46
[8]   Studies on the syntheses and reaction of nitrogen-containing heterocyclic compounds centered the naphthyridines [J].
Hamada, Y ;
Takeuchi, I .
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 2000, 120 (02) :206-223
[9]  
HANTZSCH S, 1889, J LIEBIGS AN CHEM, V250, P269
[10]  
HAWKES EM, 1973, J HETEROCYCLIC CHEM, V10, P39