One-Pot Three-Component Click Reaction of Cyclic Sulfates and Cyclic Sulfamidates

被引：20
作者：
Megia-Fernandez, Alicia [1 ]
Ortega-Munoz, Mariano [1 ]
Hernandez-Mateo, Fernando [1 ]
Santoyo-Gonzalez, Francisco [1 ]
机构：
[1] Univ Granada, Fac Ciencias, Inst Biotecnol, E-18071 Granada, Spain
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 09期
关键词：
click chemistry; cyclic sulfamidates; cyclic sulfates; cycloadditions; multi-component reactions; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; COPPER NANOPARTICLES; TERMINAL ALKYNES; DIAZO TRANSFER; MULTICOMPONENT REACTIONS; REGIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; AZIDES; CYCLOADDITION; CHEMISTRY;
D O I：
10.1002/adsc.201100813
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A one-pot, three-component methodology involving tandem azidation and click copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) of cyclic sulfates or cyclic sulfamidates in the presence of sodium azides and alkynes is reported. The developed protocol takes also advantage of the concomitant use of microwave (MW) irradiation and heterogeneous catalysis. The protocol allows the fast and efficient preparation of (alkyl sulfate)- and (alkyl sulfamidate)-1H-1,2,3-triazoles in a simple manner.
引用
收藏
页码：1797 / 1803
页数：7
相关论文
共 96 条
  • [1] Multicomponent Click Synthesis of 1,2,3-Triazoles from Epoxides in Water Catalyzed by Copper Nanoparticles on Activated Carbons
    Alonso, Francisco
    Moglie, Yanina
    Radivoy, Gabriel
    Yus, Miguel
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (20) : 8394 - 8405
  • [2] Click chemistry from organic halides, diazonium salts and anilines in water catalysed by copper nanoparticles on activated carbon
    Alonso, Francisco
    Moglie, Yanina
    Radivoy, Gabriel
    Yus, Miguel
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (18) : 6385 - 6395
  • [3] Efficient one-pot synthesis of 1-aryl 1,2,3-triazoles from aryl halides and terminal alkynes in the presence of sodium azide
    Andersen, J
    Bolvig, S
    Liang, XF
    [J]. SYNLETT, 2005, (19) : 2941 - 2947
  • [4] Synthesis and glycosidase inhibitory activity of new hexa-substituted C8-glycomimetics
    Andriuzzi, Olivia
    Gravier-Pelletier, Christine
    Bertho, Gildas
    Prange, Thierry
    Le Merrer, Yves
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2005, 1
  • [5] A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction
    Appukkuttan, P
    Dehaen, W
    Fokin, VV
    Van der Eycken, E
    [J]. ORGANIC LETTERS, 2004, 6 (23) : 4223 - 4225
  • [6] Microwave-assisted cycloaddition reactions
    Appukkuttan, Prasad
    Mehta, Vaibhav P.
    Van der Eycken, Erik V.
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (05) : 1467 - 1477
  • [7] N-(9-(9-phenylfluorenyl))homoserine-derived cyclic sulfamidates:: Novel chiral educts for the synthesis of enantiopure γ-substituted α-amino acids
    Atfani, M
    Wei, L
    Lubell, WD
    [J]. ORGANIC LETTERS, 2001, 3 (19) : 2965 - 2968
  • [8] Copper(II)/Copper(I)-Catalyzed Aza-Michael Addition/Click Reaction of in Situ Generated α-Azidohydrazones: Synthesis of Novel Pyrazolone-Triazole Framework
    Attanasi, Orazio A.
    Favi, Gianfranco
    Filippone, Paolino
    Mantellini, Fabio
    Moscatelli, Giada
    Perrulli, Francesca R.
    [J]. ORGANIC LETTERS, 2010, 12 (03) : 468 - 471
  • [9] SN2 vs. E2 on quaternary centres:: an application to the synthesis of enantiopure β2,2-amino acids
    Avenoza, A
    Busto, JH
    Corzana, F
    Jiménez-Osés, G
    Peregrina, JM
    [J]. CHEMICAL COMMUNICATIONS, 2004, (08) : 980 - 981
  • [10] Understanding the unusual regioselectivity in the nucleophilic ring-opening reactions of gem-disubstituted cyclic sulfates.: Experimental and theoretical studies
    Avenoza, A
    Busto, JH
    Corzana, F
    García, JI
    Peregrina, JM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) : 4506 - 4513
12345678910