One-pot synthesis of disubstituted imidazole derivatives from α-azido ketones catalyzed by potassium ethylxanthate

被引:22
作者
Chen, Jun [1 ]
Chen, Wenteng [1 ]
Yu, Yongping [1 ]
Zhang, Guolin [1 ]
机构
[1] Zhejiang Univ, Coll Pharmaceut Sci, Inst Mat Med, Hangzhou 310058, Zhejiang, Peoples R China
关键词
Disubstituted imidazole; alpha-Azido ketones; Potassium ethylxanthate; Catalyst; Dimerization; MARINE NATURAL-PRODUCTS; BOTRYLLUS-LEACHI; REDUCTION; ALKALOIDS;
D O I
10.1016/j.tetlet.2013.01.042
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient, novel procedure for the synthesis of new imidazole derivatives from alpha-azido ketones is described. This reaction proceeds via dimerization of aryl glyoxal imino generated from alpha-azido ketones in the presence of potassium ethylxanthate as a catalyst. A possible mechanism for the entire sequence is proposed. (c) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1572 / 1575
页数:4
相关论文
共 25 条
  • [1] Synthesis of chiral ionic liquids from natural amino acids
    Bao, WL
    Wang, ZM
    Li, YX
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) : 591 - 593
  • [2] Cathodic reduction of phenacyl azides
    Batanero, B
    Escudero, J
    Barba, F
    [J]. ORGANIC LETTERS, 1999, 1 (10) : 1521 - 1522
  • [3] Radical chain reactions of α-azido ketones with tributyltin hydride:: reduction vs nitrogen insertion and 1,2-hydrogen shift in the intermediate N-stannylaminyl radicals
    Benati, L
    Leardini, R
    Minozzi, M
    Nanni, D
    Spagnolo, P
    Strazzari, S
    Zanardi, G
    Calestani, G
    [J]. TETRAHEDRON, 2002, 58 (18) : 3485 - 3492
  • [4] p38 MAP kinase regulation of oligodendrocyte differentiation with CREB as a potential target
    Bhat, Narayan R.
    Zhang, Peisheng
    Mohanty, Sangeeta B.
    [J]. NEUROCHEMICAL RESEARCH, 2007, 32 (02) : 293 - 302
  • [5] Novel alkaloids from the red ascidian Botryllus leachi
    Durán, R
    Zubía, E
    Ortega, MJ
    Naranjo, S
    Salvá, J
    [J]. TETRAHEDRON, 1999, 55 (46) : 13225 - 13232
  • [6] Marine natural products
    Faulkner, DJ
    [J]. NATURAL PRODUCT REPORTS, 2000, 17 (01) : 7 - 55
  • [7] Grimmett M.R., 1996, COMPREHENSIVE HETERO, V3, P77
  • [8] ANTI-MYCOTIC IMIDAZOLES .4. SYNTHESIS AND ANTIFUNGAL ACTIVITY OF KETOCONAZOLE, A NEW POTENT ORALLY ACTIVE BROAD-SPECTRUM ANTIFUNGAL AGENT
    HEERES, J
    BACKX, LJJ
    MOSTMANS, JH
    VANCUTSEM, J
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (08) : 1003 - 1005
  • [9] Herrmann WA, 2002, ANGEW CHEM INT EDIT, V41, P1290, DOI 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO
  • [10] 2-Y