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
    Coleman, CM
    O'Shea, DF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (14) : 4054 - 4055
  • [3] 2-aryl indole NK1 receptor antagonists:: Optimisation of indole substitution
    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
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (09) : 1233 - 1236
  • [4] INHIBITORS OF PROTEIN-KINASE-C .1. 2,3-BISARYLMALEIMIDES
    DAVIS, PD
    HILL, CH
    LAWTON, G
    NIXON, JS
    WILKINSON, SE
    HURST, SA
    KEECH, E
    TURNER, SE
    [J]. 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
    Hugon, B
    Pfeiffer, B
    Renard, P
    Prudhomme, M
    [J]. TETRAHEDRON LETTERS, 2003, 44 (24) : 4607 - 4611
  • [7] Generation of substituted styrenes via Suzuki cross-coupling of aryl halides with 2,4,6-trivinylcyclotriboroxane
    Kerins, F
    O'Shea, DF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) : 4968 - 4971
  • [8] Indole synthesis by controlled carbolithiation of o-aminostyrenes
    Kessler, A
    Coleman, CM
    Charoenying, P
    O'Shea, DF
    [J]. 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
    KUMAR, V
    DORITY, JA
    BACON, ER
    SINGH, B
    LESHER, GY
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25) : 6995 - 6998
  • [10] Syntheses and antiproliferative activities of 7-azarebeccamycin analogues bearing one 7-azaindole moiety
    Marminon, C
    Pierré, A
    Pfeiffer, B
    Pérez, V
    Léonce, S
    Joubert, A
    Bailly, C
    Renard, P
    Hickman, J
    Prudhomme, M
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (04) : 609 - 622