Carbolithiation of vinyl pyridines as a route to 7-azaindoles

被引:25
作者
Cottineau, B [1 ]
O'Shea, DF [1 ]
机构
[1] Natl Univ Ireland Univ Coll Dublin, Dept Chem, Conway Inst, Ctr Synth & Chem Biol, Dublin 4, Ireland
关键词
7-azaindole; carbolithiation; cascade reaction;
D O I
10.1016/j.tetlet.2005.01.046
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An effective synthesis of the 7-azaindole ring system has been developed from substituted 2-amino-3-vinyl pyridines. The methodology involves a novel cascade reaction sequence of controlled carbolithiation of the vinyl double bond, subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by ring closure and dehydration. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1935 / 1938
页数:4
相关论文
共 25 条
[1]  
Clayden J., 2002, ORGANOLITHIUMS SELEC, P273
[2]   New organolithium addition methodology to diversely functionalized indoles [J].
Coleman, CM ;
O'Shea, DF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (14) :4054-4055
[3]   2-aryl indole NK1 receptor antagonists:: Optimisation of indole substitution [J].
Cooper, LC ;
Chicchi, GG ;
Dinnell, K ;
Elliott, JM ;
Hollingworth, GJ ;
Kurtz, MM ;
Locker, KL ;
Morrison, D ;
Shaw, DE ;
Tsao, KL ;
Watt, AP ;
Williams, AR ;
Swain, CJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (09) :1233-1236
[4]   INHIBITORS OF PROTEIN-KINASE-C .1. 2,3-BISARYLMALEIMIDES [J].
DAVIS, PD ;
HILL, CH ;
LAWTON, G ;
NIXON, JS ;
WILKINSON, SE ;
HURST, SA ;
KEECH, E ;
TURNER, SE .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (01) :177-184
[5]  
Hands D, 1996, SYNTHESIS-STUTTGART, P877
[6]   Synthesis of isogranulatimides A and B analogues possessing a 7-azaindole unit instead of an indole moiety [J].
Hugon, B ;
Pfeiffer, B ;
Renard, P ;
Prudhomme, M .
TETRAHEDRON LETTERS, 2003, 44 (24) :4607-4611
[7]   Generation of substituted styrenes via Suzuki cross-coupling of aryl halides with 2,4,6-trivinylcyclotriboroxane [J].
Kerins, F ;
O'Shea, DF .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) :4968-4971
[8]   Indole synthesis by controlled carbolithiation of o-aminostyrenes [J].
Kessler, A ;
Coleman, CM ;
Charoenying, P ;
O'Shea, DF .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :7836-7846
[9]   SYNTHESIS OF 7-AZAINDOLE AND 7-AZAOXINDOLE DERIVATIVES THROUGH A PALLADIUM-CATALYZED CROSS-COUPLING REACTION [J].
KUMAR, V ;
DORITY, JA ;
BACON, ER ;
SINGH, B ;
LESHER, GY .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25) :6995-6998
[10]   Syntheses and antiproliferative activities of 7-azarebeccamycin analogues bearing one 7-azaindole moiety [J].
Marminon, C ;
Pierré, A ;
Pfeiffer, B ;
Pérez, V ;
Léonce, S ;
Joubert, A ;
Bailly, C ;
Renard, P ;
Hickman, J ;
Prudhomme, M .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (04) :609-622