Synthesis and functionalization of N-sulfinyl imines: Sonogashira reaction and copper-catalyzed azide-alkyne cycloaddition

被引：2
|
作者：
Souza, Frederico B. [1 ]
Vasconcelos, Stanley N. S. [1 ]
Reis, Joel S. [1 ]
Pimenta, Daniel C. [2 ]
Stefani, Helio [1 ]
机构：
[1] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farmacia, Sao Paulo, Brazil
[2] Inst Butantan, Sao Paulo, Brazil
来源：
TETRAHEDRON LETTERS | 2017年 / 58卷 / 11期
基金：
巴西圣保罗研究基金会;
关键词：
N-sulfinyl imines; Sonogashira reaction; Heterocycle; Cycloaddition; Triazole; ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS; LIGANDS; CHEMISTRY; TRIAZOLE;
D O I：
10.1016/j.tetlet.2017.01.107
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A small library of novel molecules was generated using a rapid and efficient methodology for the synthesis of N-sulfinyl imine triazole compounds. The process involves a coupling step from the Sonogashira cross-coupling reaction and then, in a one-step reaction, deprotection of the trimethylsilyl group and triazole heterocyclic ring formation using a microwave reactor. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1057 / 1060
页数：4
相关论文
共 50 条
  • [1] The mechanism of copper-catalyzed azide-alkyne cycloaddition reaction: A quantum mechanical investigation
    Ozen, Cihan
    Tuzun, Nurcan S.
    JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2012, 34 : 101 - 107
  • [2] Analysis and Optimization of Copper-Catalyzed Azide-Alkyne Cycloaddition for Bioconjugation
    Hong, Vu
    Presolski, Stanislav I.
    Ma, Celia
    Finn, M. G.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9879 - 9883
  • [3] Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction in Water Using Cyclodextrin as a Phase Transfer Catalyst
    Shin, Jung-Ah
    Lim, Yeong-Gweon
    Lee, Kyung-Hee
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (08) : 4117 - 4122
  • [4] Photocatalytic copper-catalyzed azide-alkyne cycloaddition click reaction with Cu(II) coordination polymer
    Guo, Xiangyang
    Zeng, Le
    Wang, Zhe
    Zhang, Tiexin
    He, Cheng
    Duan, Chunying
    RSC ADVANCES, 2017, 7 (83): : 52907 - 52913
  • [5] Copper-catalyzed alkyne-azide cycloaddition for the functionalization of fullerene building blocks
    Nierengarten, Jean-Francois
    PURE AND APPLIED CHEMISTRY, 2012, 84 (04) : 1027 - 1037
  • [6] Asymmetric Copper-Catalyzed Azide-Alkyne Cycloadditions
    Brittain, William D. G.
    Buckley, Benjamin R.
    Fossey, John S.
    ACS CATALYSIS, 2016, 6 (06): : 3629 - 3636
  • [7] Head-to-tail peptide cyclodimerization by copper-catalyzed azide-alkyne cycloaddition
    Punna, S
    Kuzelka, J
    Wang, Q
    Finn, MG
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (15) : 2215 - 2220
  • [8] On the Mechanism of Copper(I)-Catalyzed Azide-Alkyne Cycloaddition
    Zhu, Lei
    Brassard, Christopher J.
    Zhang, Xiaoguang
    Guha, P. M.
    Clark, Ronald J.
    CHEMICAL RECORD, 2016, 16 (03) : 1501 - 1517
  • [9] Chalcones and Chromones in Copper-catalyzed Azide-Alkyne Cycloadditions (CuAAC)
    Tome, Sara M.
    Tome, Augusto C.
    Soengas, Raquel G.
    Silva, Artur M. S.
    CURRENT ORGANIC CHEMISTRY, 2018, 22 (13) : 1307 - 1325
  • [10] Beyond copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition: Synthesis and mechanism insights
    Gomes, Roberto S.
    Jardim, Guilherme A. M.
    de Carvalho, Renato L.
    Araujo, Maria H.
    da Silva Junior, Eufranio N.
    TETRAHEDRON, 2019, 75 (27) : 3697 - 3712
12345