Aza-annulation of polarized N,S- and N,N-ketene acetals with itaconic anhydride: Synthesis of novel functionalized 1,2,3,4-tetrahydro-2-pyridones and related azabicycles

被引:51
作者
Chakrabarti, S
Panda, K
Misra, NC
Ila, H [1 ]
Junjappa, H
机构
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
[2] BioOrgan Appl Mat Pvt Ltd, Bangalore 560058, Karnataka, India
关键词
alkaloids; annulation; esters; heterocycles; lactams; Michael addition; nitriles;
D O I
10.1055/s-2005-868491
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of novel highly functionalized 2-oxo-(1,2,3,4-tetrahydropyridin-3-yl) acetic acids has been described via aza-annulation of both acyclic and cyclic alpha-oxo- and alpha-nitro-N,S-and-N,N-ketene acetals with itaconic anhydride.
引用
收藏
页码:1437 / 1441
页数:5
相关论文
共 51 条
  • [1] Synthesis of enantiopure cis- and trans-2,3-disubstituted piperidines
    Agami, C
    Dechoux, L
    Ménard, C
    Hebbe, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) : 7573 - 7576
  • [2] Enantioselective synthesis of conformationally restricted analogs of NMDA: cis- and trans-piperidine-2,3-dicarboxylic acids and methylated derivatives
    Agami, C
    Hamon, L
    KadouriPuchot, C
    LeGuen, V
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) : 5736 - 5742
  • [3] AGGARWAL V, 1982, SYNTHESIS-STUTTGART, P65
  • [4] AGGARWAL V, 1983, SYNTHESIS-STUTTGART, P147
  • [5] THE ASYMMETRIC MICHAEL REACTION USING CHIRAL IMINES UNDER NEUTRAL CONDITIONS - STEREOCHEMICAL EVIDENCES IN SUPPORT OF A CYCLIC TRANSITION-STATE
    AMBROISE, L
    DESMAELE, D
    MAHUTEAU, J
    DANGELO, J
    [J]. TETRAHEDRON LETTERS, 1994, 35 (52) : 9705 - 9708
  • [6] Balasubramanian M., 1996, COMPREHENSIVE HETERO, V5, P245, DOI 10.1016/B978-008096518-5.00109
  • [7] ASYMMETRIC FORMATION OF QUATERNARY CENTERS THROUGH AZA-ANNULATION OF CHIRAL BETA-ENAMINO ESTERS WITH ACRYLATE DERIVATIVES
    BARTA, NS
    BRODE, A
    STILLE, JR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) : 6201 - 6206
  • [8] A facile access to 2-methylthio/alkoxy/amino-3-acylimidazo[1,2-a]pyridines based on cupric chloride promoted oxidative ring closure of α-oxoketene N,S-, N,O-, and N,N-acetals
    Barun, HO
    Ila, H
    Junjappa, H
    Singh, OM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) : 1583 - 1587
  • [9] Ring annulation with tetrahydroisoquinoline-derived enaminones:: Highly convergent routes to functionalized pyrrolo[2,1-a]- and indolo[2,1-a]isoquinolines
    Barun, O
    Chakrabarti, S
    Ila, H
    Junjappa, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) : 4457 - 4461
  • [10] Barun O, 2000, SYNLETT, P653