A Simple Copper-Catalyzed Cascade Synthesis of 2-Amino-1H-indole-3-carboxylate Derivatives

被引：54
作者：
Yang, Xiaobo [1 ,2 ]
Fu, Hua [1 ]
Qiao, Renzhong [2 ]
Jiang, Yuyang [1 ,3 ]
Zhao, Yufen [1 ]
机构：
[1] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China
[2] Beijing Univ Chem Technol, Coll Life Sci & Technol, State Key Lab Chem Resource Engn, Dept Pharmaceut Engn, Beijing 100029, Peoples R China
[3] Tsinghua Univ, Grad Sch Shenzhen, Key Lab Chem Biol Guangdong Prov, Shenzhen 518057, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 06期
基金：
中国国家自然科学基金;
关键词：
2-amino-1H-indole-3-carboxylates; cascade reactions; copper; nitrogen heterocycles; synthetic methods; HIGHLY FUNCTIONALIZED INDOLES; ONE-POT SYNTHESIS; C-O; EFFICIENT SYNTHESIS; COUPLING REACTIONS; AMIDINE HYDROCHLORIDES; NITROGEN-HETEROCYCLES; ORTHO-SUBSTITUENT; ROOM-TEMPERATURE; ARYL HALIDES;
D O I：
10.1002/adsc.200900887
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
We have developed a simple and efficient copper-catalyzed method for the synthesis of 2-amino-1H-indole-3-carboxylate derivatives via cascade reactions of substituted N-(2-halophenyl)-2,2,2-trifluoroacetamide with alkyl 2-cyanoacetate or malononitrile under mild conditions, and the method is of wide practical application.
引用
收藏
页码：1033 / 1038
页数：6
相关论文
共 65 条
  • [1] A domino copper-catalyzed C-N and C-O cross-coupling for the conversion of primary amides into benzoxazoles
    Altenhoff, G
    Glorius, F
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) : 1661 - 1664
  • [2] [Anonymous], 2009, ANGEW CHEM-GER EDIT
  • [3] [Anonymous], 2007, ANGEW CHEM
  • [4] [Anonymous], ANGEW CHEM
  • [5] [Anonymous], 2006, Angew. Chem, DOI DOI 10.1002/ANGE.200602917
  • [6] Cascade alkenyl amination/heck reaction promoted by a bifunctional palladium catalyst:: A novel one-pot synthesis of indoles from o-haloanilines and alkenyl halides
    Barluenga, J
    Fernández, MA
    Aznar, F
    Valdés, C
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (08) : 2276 - 2283
  • [7] Barraja P, 2004, ANTICANCER RES, V24, P3775
  • [8] Copper in cross-coupling reactions - The post-Ullmann chemistry
    Beletskaya, IP
    Cheprakov, AV
    [J]. COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) : 2337 - 2364
  • [9] Synthesis and reactivity of N-hydroxy-2-aminoindoles
    Belley, M
    Sauer, E
    Beaudoin, D
    Duspara, P
    Trimble, LA
    Dubé, P
    [J]. TETRAHEDRON LETTERS, 2006, 47 (02) : 159 - 162
  • [10] Rapid access to oxindoles by the combined use of an Ugi four-component reaction and a microwave-assisted intramolecular Buchwald-Hartwig amidation reaction
    Bonnaterre, Florence
    Bois-Choussy, Michele
    Zhu, Jieping
    [J]. ORGANIC LETTERS, 2006, 8 (19) : 4351 - 4354
1234567