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
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
  • [41] N-heterocyclic Thiols based Copper Complexes: Syntheses, Structure and Catalytic Studies for Azide-Alkyne Cycloaddition Reaction
    Yadav, Suraj Peerappa
    Sahil, Deepika
    Chauhan, Rohit Singh
    Butcher, R. J.
    Tyagi, Adish
    Karmakar, Gourab
    Dash, Chandrakanta
    CHEMISTRYSELECT, 2024, 9 (01):
  • [42] Probing glycans with the copper(I)-catalyzed [3+2] azide-alkyne cycloaddition
    Hanson, Sarah R.
    Greenberg, William A.
    Wong, Chi-Huey
    QSAR & COMBINATORIAL SCIENCE, 2007, 26 (11-12): : 1243 - 1252
  • [43] Simultaneous copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) and living radical polymerization
    Geng, Jin
    Lindqvist, Josefina
    Mantovani, Giuseppe
    Haddleton, David M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) : 4180 - 4183
  • [44] Mechanism of the ligand-free CuI-catalyzed azide-alkyne cycloaddition reaction
    Rodionov, VO
    Fokin, VV
    Finn, MG
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (15) : 2210 - 2215
  • [45] Click chemistry in materials synthesis. II. Acid-swellable crosslinked polymers made by copper-catalyzed azide-alkyne cycloaddition
    Li, Chunmei
    Finn, M. G.
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2006, 44 (19) : 5513 - 5518
  • [46] Synthesis and Characterization of the Azido-Functionalized Ruthenocene Analogue [TpmRu(p-N3C6H4)Tp]Cl and Its Attachment to Biomolecules by Copper-Catalyzed Azide-Alkyne Cycloaddition
    Zagermann, Johannes
    Klein, Kathrin
    Merz, Klaus
    Molon, Mariusz
    Metzler-Nolte, Nils
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2011, (27) : 4212 - 4219
  • [47] Tailoring the Hydrophilic/Lipophilic Balance of Clickable Mesoporous Organosilicas by the Copper-Catalyzed Azide Alkyne Cycloaddition Click-Functionalization
    Noureddine, Achraf
    Trens, Philippe
    Toquer, Guillaume
    Cattoen, Xavier
    Man, Michel Wong Chi
    LANGMUIR, 2014, 30 (41) : 12297 - 12305
  • [48] First example of "click" copper(I) catalyzed azide-alkyne cycloaddition in supercritical carbon dioxide: application to the functionalization of aliphatic polyesters
    Grignard, Bruno
    Schmeits, Stephanie
    Riva, Raphael
    Detrembleur, Christophe
    Lecomte, Philippe
    Jerome, Christine
    GREEN CHEMISTRY, 2009, 11 (10) : 1525 - 1529
  • [49] Copper-Catalyzed Aza-Iminosydnone-Alkyne Cycloaddition Reaction Discovered by Screening
    Decuypere, Elodie
    Bernard, Sabrina
    Feng, Minghao
    Porte, Karine
    Riomet, Margaux
    Thuery, Pierre
    Audisio, Davide
    Taran, Frederic
    ACS CATALYSIS, 2018, 8 (12): : 11882 - 11888
  • [50] Azide-Alkyne Cycloaddition Reaction Catalyzed by Cu(II) Complexes: Studies on the effect of Different Ligand Systems
    Kumari, Sheela
    Singh, Sain
    Ghosh, Kaushik
    CHEMISTRYSELECT, 2023, 8 (32):