Applications of Baylis-Hillman acetates:: one-pot, facile and convenient synthesis of substituted γ-lactams

被引:79
作者
Basavaiah, D [1 ]
Rao, JS [1 ]
机构
[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India
关键词
Baylis-Hillman chemistry; gamma-lactams; reductive cyclization; Fe/AcOH;
D O I
10.1016/j.tetlet.2003.12.133
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, convenient and one-pot transformation of the acetates of Baylis-Hillman adducts into substituted gamma-lactams, that is, (E)-5-alkyl-3-arylidenepyrrolidin-2-ones via treatment with nitroalkanes in the presence of a base, followed by reductive cyclization, using Fe/AcOH, is described. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1621 / 1625
页数:5
相关论文
共 71 条
  • [1] Correlation between pKa and reactivity of quinuclidine-based catalysts in the Baylis-Hillman reaction:: Discovery of quinuclidine as optimum catalyst leading to substantial enhancement of scope
    Aggarwal, VK
    Emme, I
    Fulford, SY
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) : 692 - 700
  • [2] Reaction of a cyclic oxosulfonium ylide with acetates of the Baylis-Hillman adducts: Tandem Michael-intramolecular Corey-Chaykovsky reactions
    Akiyama, H
    Fujimoto, T
    Ohshima, K
    Hoshino, K
    Yamamoto, I
    Iriye, R
    [J]. ORGANIC LETTERS, 1999, 1 (03) : 427 - 430
  • [3] Akiyama H, 2001, EUR J ORG CHEM, V2001, P2265, DOI 10.1002/1099-0690(200106)2001:12<2265::AID-EJOC2265>3.0.CO
  • [4] 2-8
  • [5] An easy and stereoselective synthesis of N-Boc-dolaproine via the Baylis-Hillman reaction
    Almeida, WP
    Coelho, F
    [J]. TETRAHEDRON LETTERS, 2003, 44 (05) : 937 - 940
  • [6] GAMMA-LACTAM ANALOGS OF CARBAPENICILLANIC ACIDS
    BALDWIN, JE
    ADLINGTON, RM
    JONES, RH
    SCHOFIELD, CJ
    ZARACOSTAS, C
    GREENGRASS, CW
    [J]. TETRAHEDRON, 1986, 42 (17) : 4879 - 4888
  • [7] A GAMMA-LACTAM ANALOG OF THE PENEMS POSSESSING ANTIBACTERIAL ACTIVITY
    BALDWIN, JE
    FREEMAN, RT
    LOWE, C
    SCHOFIELD, CJ
    LEE, E
    [J]. TETRAHEDRON, 1989, 45 (14) : 4537 - 4550
  • [8] Asymmetric Baylis-Hillman reactions: catalysis using a chiral pyrrolizidine base
    Barrett, AGM
    Cook, AS
    Kamimura, A
    [J]. CHEMICAL COMMUNICATIONS, 1998, (22) : 2533 - 2534
  • [9] Applications of Baylis-Hillman chemistry:: one-pot convenient synthesis of functionalized (1H)-quinol-2-ones and quinolines
    Basavaiah, D
    Reddy, RM
    Kumaragurubaran, N
    Sharada, DS
    [J]. TETRAHEDRON, 2002, 58 (19) : 3693 - 3697
  • [10] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction
    Basavaiah, D
    Rao, PD
    Hyma, RS
    [J]. TETRAHEDRON, 1996, 52 (24) : 8001 - 8062