An Organocatalytic Azide-Aldehyde [3+2] Cycloaddition: High-Yielding Regioselective Synthesis of 1,4-Disubstituted 1,2,3-Triazoles

被引：190
|
作者：
Ramachary, Dhevalapally B. [1 ]
Shashank, Adluri B. [1 ]
Karthik, S. [1 ]
机构：
[1] Univ Hyderabad, Catalysis Lab, Sch Chem, Hyderabad 500046, Andhra Pradesh, India
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 39期
关键词：
1,2,3-triazoles; aldehydes; azides; click chemistry; organocatalysis; RUTHENIUM-CATALYZED CYCLOADDITION; FREE CLICK CHEMISTRY; ALKYNE CYCLOADDITION; DIRECT ACCESS; TRIAZOLINES; EFFICIENT; INHIBITOR; KETONES; STRAIN; AMINE;
D O I：
10.1002/anie.201406721
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An organocatalytic azide-aldehyde [3+2] cycloaddition (organo-click) reaction of a variety of enolizable aldehydes is reported. The organo-click reaction is characterized by a high rate and regioselectivity, mild reaction conditions, easily available substrates with simple operation, and excellent yields with a broad spectrum of substrates. It constitutes an alternative to the previously known CuAAC, RuAAC, and IrAAC click reactions.
引用
收藏
页码：10420 / 10424
页数：5
相关论文
共 50 条
  • [1] An Enolate-Mediated Organocatalytic Azide-Ketone [3+2]-Cycloaddition Reaction: Regioselective High-Yielding Synthesis of Fully Decorated 1,2,3-Triazoles
    Shashank, Adluri B.
    Karthik, S.
    Madhavachary, R.
    Ramachary, Dhevalapally B.
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (51) : 16877 - 16881
  • [2] Organocatalytic Vinyl Azide-Carbonyl [3+2] Cycloaddition: High-Yielding Synthesis of Fully Decorated N-Vinyl-1,2,3-Triazoles
    Ramachary, Dhevalapally B.
    Reddy, G. Surendra
    Peraka, Swamy
    Gujral, Jagjeet
    CHEMCATCHEM, 2017, 9 (02) : 263 - 267
  • [3] Conventional and microwave assisted synthesis of 1,4-disubstituted 1,2,3-triazoles from Huisgen cycloaddition
    Sarmiento-Sanchez, Juan I.
    Ochoa-Teran, Adrian
    Rivero, Ignacio A.
    ARKIVOC, 2011, : 177 - 188
  • [4] Enamine/Enolate-Mediated Organocatalytic Azide-Carbonyl [3+2] Cycloaddition Reactions for the Synthesis of Densely Functionalized 1,2,3-Triazoles
    Ramasastry, Sripada S. V.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (52) : 14310 - 14312
  • [5] A facile and regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles using click chemistry
    Kumar, Dalip
    Reddy, V. Buchi
    Varma, Rajender S.
    TETRAHEDRON LETTERS, 2009, 50 (18) : 2065 - 2068
  • [6] Organocatalytic enone-azide [3+2]-cycloaddition: synthesis of functionally richC/N-double vinyl 1,2,3-triazoles
    Reddy, G. Surendra
    Kumar, A. Suresh
    Ramachary, Dhevalapatly B.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (23) : 4470 - 4478
  • [7] Azide/Alkyne Resins for Quick Preparation of 1,4-Disubstituted 1,2,3-Triazoles
    Sirion, Uthaiwan
    Lee, Jae Hak
    Bae, Yu Jin
    Kim, Hee Jun
    Lee, Byoung Se
    Chi, Dae Yoon
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2010, 31 (07) : 1843 - 1847
  • [8] An Organocatalytic Regiospecific Synthesis of 1,5-Disubstituted 4-Thio-1,2,3-triazoles and 1,5-Disubstituted 1,2,3-Triazoles
    Ramachary, Dhevalapally B.
    Krishna, Patoju M.
    Gujral, Jagjeet
    Reddy, G. Surendra
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (47) : 16775 - 16780
  • [9] One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from nitrobenzenes
    Zhao, Fen
    Chen, Zhen
    Xie, Kai
    Yang, Rui
    Jiang, Yu-Bo
    CHINESE CHEMICAL LETTERS, 2016, 27 (01) : 109 - 113
  • [10] A Facile One-Pot Metal-Free Synthesis of 1,4-Disubstituted 1,2,3-Triazoles
    Jia, Qianfa
    Yang, Gongming
    Chen, Lei
    Du, Zhiyun
    Wei, Jia
    Zhong, Yanqiong
    Wang, Jian
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (16) : 3435 - 3440
12345