Synthesis of a novel series of 4,4-disubstituted 2,3,4,7-tetrahydroazepines

被引:9
作者
Barberis, M [1 ]
García-Losada, P [1 ]
Pleite, S [1 ]
Rodríguez, JR [1 ]
Soriano, JF [1 ]
Mendiola, J [1 ]
机构
[1] Lilly SA, Madrid 28108, Spain
关键词
azepine; metathesis; pyrrolidinone; Wittig;
D O I
10.1016/j.tetlet.2005.05.088
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general, simple and straightforward strategy for the synthesis of a novel series of 4,4-disubstituted 2,3,4,7-tetrahydroazepines is described. This route involves a one-pot Wittig olefination/N-allylation process on a five-membered hemi-aminal followed by a final ring closing metathesis reaction. (c) 2005 Published by Elsevier Ltd.
引用
收藏
页码:4847 / 4850
页数:4
相关论文
共 36 条
  • [1] [Anonymous], 2003, HDB METATHESIS
  • [2] BELENKII LJ, 1988, ADV HETEROCYCLIC CHE, V44, pCH4
  • [3] INTRAMOLECULAR REACTION BETWEEN A DIAZOALKANE GROUP AND AN ESTER GROUP - SEARCH FOR OTHER EXAMPLES
    BILLETT, EH
    FLEMING, I
    HANSON, SW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (16): : 1661 - 1668
  • [4] ALUMINUM CHLORIDE-PROMOTED AMINOLYSIS OF N-TOSYL LACTAMS
    BON, E
    BIGG, DCH
    BERTRAND, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (07) : 1904 - 1906
  • [5] BROSSI A, 1992, ALKALOIDS CHEM PHARM
  • [6] CACHOUX F, 2002, SYN LETT, V12, P1987
  • [7] Recent developments in olefin cross-metathesis
    Connon, SJ
    Blechert, S
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (17) : 1900 - 1923
  • [8] Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis
    Deiters, A
    Martin, SF
    [J]. CHEMICAL REVIEWS, 2004, 104 (05) : 2199 - 2238
  • [9] Enyne metathesis (enyne bond reorganization)
    Diver, ST
    Giessert, AJ
    [J]. CHEMICAL REVIEWS, 2004, 104 (03) : 1317 - 1382
  • [10] STEREOSELECTIVE DOUBLE ALKYLATION OF ETHYL N-BOC-PYROGLUTAMATE
    EZQUERRA, J
    PEDREGAL, C
    RUBIO, A
    VAQUERO, JJ
    MATIA, MP
    MARTIN, J
    DIAZ, A
    NAVIO, JLG
    DEETER, JB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) : 4327 - 4331