An efficient multicomponent reaction involving the interception of the zwitterionic intermediate between DMAD and isocyanides with some active methylene compounds

被引:37
作者
Nair, V [1 ]
Vinod, AU
Ramesh, R
Menon, RS
Varma, L
Mathew, S
Chiaroni, A
机构
[1] CSIR, Reg Res Lab, Div Organ Chem, Trivandrum 695019, Kerala, India
[2] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
D O I
10.3987/COM-02-S(M)62
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 1:1 zwitterionic intermediate generated from dimethyl acetylenedicarboxylate and isocyanide is intercepted with 2-hydroxy-1,4-naphthoquinone, 4-hydroxycoumarin, 4-hydroxy-1-methylquinolinone, 4-hydroxy-6-methylpyrone, and 1-naphthol in one-pot to give novel pyran annulated heterocyclic systems in good yields.
引用
收藏
页码:147 / 151
页数:5
相关论文
共 13 条
  • [1] The discovery of new isocyanide-based multi-component reactions
    Dömling, A
    [J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 2000, 4 (03) : 318 - 323
  • [2] Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
  • [3] 2-U
  • [4] STRUCTURE OF ISOFERPRENIN, A 4-HYDROXYCOUMARIN DERIVATIVE FROM FERULA-COMMUNIS VAR GENUINA
    LAMNAOUER, D
    FRAIGUI, O
    MARTIN, MT
    GALLARD, JF
    BODO, B
    [J]. JOURNAL OF NATURAL PRODUCTS, 1991, 54 (02): : 576 - 578
  • [5] A novel synthesis of 2-aminopyrroles using a three-component reaction
    Nair, V
    Vinod, AU
    Rajesh, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) : 4427 - 4429
  • [6] The reaction of cyclohexyl isocyanide and dimethyl acetylenedicarboxylate with o- and p-quinones:: a novel synthesis of iminolactones
    Nair, V
    Vinod, AU
    Nair, JS
    Sreekanth, AR
    Rath, NP
    [J]. TETRAHEDRON LETTERS, 2000, 41 (34) : 6675 - 6679
  • [7] The reaction of cyclohexyl isocyanide and dimethyl acetylenedicarboxylate with aldehydes: a novel synthesis of 2-aminofuran derivatives
    Nair, V
    Vinod, AU
    [J]. CHEMICAL COMMUNICATIONS, 2000, (12) : 1019 - 1020
  • [8] MULTICOMPONENT REACTIONS IN ORGANIC-CHEMISTRY
    UGI, I
    DOMLING, A
    HORL, W
    [J]. ENDEAVOUR, 1994, 18 (03) : 115 - 122
  • [9] Ugi I., 1991, COMPREHENSIVE ORGANI, P1083
  • [10] UGI I, 1973, ORG SYNTH, V5, P300