One-pot construction of pyrazoles and isoxazoles with palladium-catalyzed four-component coupling

被引:215
作者
Ahmed, MSM [1 ]
Kobayashi, K [1 ]
Mori, A [1 ]
机构
[1] Tokyo Inst Technol, Chem Resources Lab, Yokohama, Kanagawa 2268503, Japan
关键词
D O I
10.1021/ol051841j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Four-component coupling of a terminal alkyne, hydrazine (hydroxylamine), carbon monoxide, and an aryl iodide furnishes pyrazole or isoxazole derivatives in the presence of a palladium catalyst. The reaction proceeds at room temperature and an ambient pressure of carbon monoxide in an aqueous solvent system.
引用
收藏
页码:4487 / 4489
页数:3
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共 21 条
  • [1] The synthesis of novel heterocyclic substituted α-amino acids;: further exploitation of α-amino acid alkynyl ketones as reactive substrates
    Adlington, RM
    Baldwin, JE
    Catterick, D
    Pritchard, GJ
    Tang, LT
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (15): : 2311 - 2316
  • [2] Ahmed MSM, 2005, B CHEM SOC JPN, V78, P160
  • [3] Carbonylative Sonogashira coupling of terminal alkynes with aqueous ammonia
    Ahmed, MSM
    Mori, A
    [J]. ORGANIC LETTERS, 2003, 5 (17) : 3057 - 3060
  • [4] Regioselective synthesis of 1,3,5-substituted pyrazoles from acetylenic ketones and hydrazines
    Bishop, BC
    Brands, KMJ
    Gibb, AD
    Kennedy, DJ
    [J]. SYNTHESIS-STUTTGART, 2004, (01): : 43 - 52
  • [5] Campbell I. B., 1994, ORGANOCOPPER REAGENT, P217
  • [6] Propargyladehyds and the phenylpropargyaldehyds
    Claisen, L
    [J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1903, 36 : 3664 - 3673
  • [7] REACTION OF 1-PHENYL-2-PROPYN-1-ONE WITH HYDRAZINE DERIVATIVES
    ENGELMANN, A
    KIRMSE, W
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (09): : 3092 - 3094
  • [8] New flexible synthesis of pyrazoles with different, functionalized substituents at C3 and C5
    Grotjahn, DB
    Van, S
    Combs, D
    Lev, DA
    Schneider, C
    Rideout, M
    Meyer, C
    Hernandez, G
    Mejorado, L
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (26) : 9200 - 9209
  • [9] CONVERSION OF SOME ALPHA-ACETYLENIC KETONES AND RELATED ALPHABETA-DIBROMOKETONES INTO 3,5-DIARYLISOXAZOLES
    JOHNSTON, KM
    SHOTTER, RG
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (14): : 1774 - &
  • [10] In situ selection of lead compounds by click chemistry: Target-guided optimization of acetylcholinesterase inhibitors
    Krasinski, A
    Radic, Z
    Manetsch, R
    Raushel, J
    Taylor, P
    Sharpless, KB
    Kolb, HC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (18) : 6686 - 6692