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Volumn 16, Issue 8, 2014, Pages 381-385

Ionic liquid-phase synthesis of 1,5-disubstituted 1,2,3-triazoles

Author keywords

heterocyclic compound; ionic liquid; triazole

Indexed keywords

BENZYL CHLORIDE; BENZYL DERIVATIVE; IONIC LIQUID; TRIAZOLE DERIVATIVE;

EID: 84905864956     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co500065e     Document Type: Article
Times cited : (29)

References (31)
  • 1
    • 0020677250 scopus 로고
    • Studies on v-triazoles. 7. Antiallergic 9-oxo-1 H,9 H -benzopyrano[2,3- d ]-v-triazoles
    • Buckel, D. R.; Outred, D. J.; Rockell, C. J. M.; Smith, H.; Spicer, B. A. Studies on v-triazoles. 7. Antiallergic 9-oxo-1 H,9 H -benzopyrano[2,3- d ]-v-triazoles J. Med. Chem. 1983, 26, 251-254
    • (1983) J. Med. Chem. , vol.26 , pp. 251-254
    • Buckel, D.R.1    Outred, D.J.2    Rockell, C.J.M.3    Smith, H.4    Spicer, B.A.5
  • 2
    • 0023018014 scopus 로고
    • Studies on 1,2,3-triazoles. 13. (Piperazinylalkoxy)-[1]benzopyrano[2,3- d ]-1,2,3-triazol-9(1 H)-ones with combined H1-antihistamine and mast cell stabilizing properties
    • Buckle, D. R.; Rockell, C. J. M.; Smith, H.; Spicer, B. A. Studies on 1,2,3-triazoles. 13. (Piperazinylalkoxy)-[1]benzopyrano[2,3- d ]-1,2,3-triazol-9(1 H)-ones with combined H1-antihistamine and mast cell stabilizing properties J. Med. Chem. 1986, 29, 2262-2267
    • (1986) J. Med. Chem. , vol.29 , pp. 2262-2267
    • Buckle, D.R.1    Rockell, C.J.M.2    Smith, H.3    Spicer, B.A.4
  • 3
    • 0028063421 scopus 로고
    • 1,2,3-Triazole-[2,5-bis- O -(tert-butyldimethylsilyl)-β- d -ribofuranosyl]-3′-spiro-5-(4-amino-1,2-oxathiole 2,2-dioxide) (TSAO) analogs: Synthesis and anti-HIV-1 activity
    • Alvarez, R.; Velazquez, S.; San-Felix, A.; Aquaro, S.; De Clercq, E.; Perno, C.-F.; Karlsson, A.; Balzarini, J.; Camarasa, M. J. 1,2,3-Triazole-[2,5- bis- O -(tert-butyldimethylsilyl)-β- d -ribofuranosyl]-3′-spiro-5-(4- amino-1,2-oxathiole 2,2-dioxide) (TSAO) analogs: Synthesis and anti-HIV-1 activity J. Med. Chem. 1994, 37, 4185-4194
    • (1994) J. Med. Chem. , vol.37 , pp. 4185-4194
    • Alvarez, R.1    Velazquez, S.2    San-Felix, A.3    Aquaro, S.4    De Clercq, E.5    Perno, C.-F.6    Karlsson, A.7    Balzarini, J.8    Camarasa, M.J.9
  • 5
    • 0037182352 scopus 로고    scopus 로고
    • Synthesis of 1′-β- d -glucopyranosyl-1,2,3-triazole-4,5- dimethanol-4,5-bis(isopropylcarbamate) as potential antineoplastic agent
    • Al-Masoudim, N. A.; Al-Soud, Y. A. Synthesis of 1′-β- d -glucopyranosyl-1,2,3-triazole-4,5-dimethanol-4,5-bis(isopropylcarbamate) as potential antineoplastic agent Tetrahedron Lett. 2002, 43, 4021-4022
    • (2002) Tetrahedron Lett. , vol.43 , pp. 4021-4022
    • Al-Masoudim, N.A.1    Al-Soud, Y.A.2
  • 6
    • 0038676244 scopus 로고    scopus 로고
    • Syntheses of examples of the 5,6-dihydro-4 H -[1,2,3]triazolo[4,5,1- ij ]quinoline, 4,5,6,7-tetrahydro[1,2,3]triazolo[4,5,1- jk ][1,4]benzodiazepine, and 5,6,7,8-tetrahydro-4 H -[1,2,3]triazolo[4,5,1- kl ][1]benzazocine ring systems
    • Katritzky, A. R.; Bobrov, S.; Kirichenko, K.; Ji, Y.; Steel, P. J. Syntheses of examples of the 5,6-dihydro-4 H -[1,2,3]triazolo[4,5,1- ij ]quinoline, 4,5,6,7-tetrahydro[1,2,3]triazolo[4,5,1- jk ][1,4]benzodiazepine, and 5,6,7,8-tetrahydro-4 H -[1,2,3]triazolo[4,5,1- kl ][1]benzazocine ring systems J. Org. Chem. 2003, 68, 5713-5719
    • (2003) J. Org. Chem. , vol.68 , pp. 5713-5719
    • Katritzky, A.R.1    Bobrov, S.2    Kirichenko, K.3    Ji, Y.4    Steel, P.J.5
  • 8
    • 33644543734 scopus 로고    scopus 로고
    • Catalytic click rotaxanes: A substoichiometric metal-template pathway to mechanically interlocked Archi
    • Aucagne, V.; Hänni, K. D.; Leigh, D. A.; Lusby, P. J.; Walker, D. B. Catalytic click rotaxanes: A substoichiometric metal-template pathway to mechanically interlocked Archi J. Am. Chem. Soc. 2006, 128, 2186-2187
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 2186-2187
    • Aucagne, V.1    Hänni, K.D.2    Leigh, D.A.3    Lusby, P.J.4    Walker, D.B.5
  • 9
    • 33646500800 scopus 로고    scopus 로고
    • Triazole-based monophosphine ligands for palladium-catalyzed cross-coupling reactions of aryl chloridestectu
    • Dai, Q.; Gao, W.; Liu, D.; Kapes, L. M.; Zhang, X. Triazole-based monophosphine ligands for palladium-catalyzed cross-coupling reactions of aryl chloridestectu J. Org. Chem. 2006, 71, 3928-3934
    • (2006) J. Org. Chem. , vol.71 , pp. 3928-3934
    • Dai, Q.1    Gao, W.2    Liu, D.3    Kapes, L.M.4    Zhang, X.5
  • 10
    • 34848859255 scopus 로고    scopus 로고
    • Synthesis of pentafluorosulfanylpyrazole and pentafluorosulfanyl-1,2,3- triazole and their derivatives as energetic materials by click chemistry
    • Ye, C. F.; Gard, G. L.; Winter, R. W.; Syvret, R. G.; Twamley, B.; Shreeve, J. M. Synthesis of pentafluorosulfanylpyrazole and pentafluorosulfanyl- 1,2,3-triazole and their derivatives as energetic materials by click chemistry Res. Org. Lett. 2007, 9, 3841-3844
    • (2007) Res. Org. Lett. , vol.9 , pp. 3841-3844
    • Ye, C.F.1    Gard, G.L.2    Winter, R.W.3    Syvret, R.G.4    Twamley, B.5    Shreeve, J.M.6
  • 11
    • 51049094897 scopus 로고    scopus 로고
    • Cu-catalyzed azide-alkyne cycloaddition
    • Meldal, M.; Tornoe, C. W. Cu-catalyzed azide-alkyne cycloaddition Chem. Rev. 2008, 108, 2952-3015
    • (2008) Chem. Rev. , vol.108 , pp. 2952-3015
    • Meldal, M.1    Tornoe, C.W.2
  • 12
    • 67749139798 scopus 로고    scopus 로고
    • Oxidative palladium catalysis in SNAr reactions leading to heteroaryl ethers from pyridotriazol-1-yloxy heterocycles with aryl boronic acids
    • Wacharasindhu, S.; Bardhan, S.; Wan, Z.-K.; Tabei, K.; Mansour, T. S. Oxidative palladium catalysis in SNAr reactions leading to heteroaryl ethers from pyridotriazol-1-yloxy heterocycles with aryl boronic acids J. Am. Chem. Soc. 2009, 131, 4174-4175
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 4174-4175
    • Wacharasindhu, S.1    Bardhan, S.2    Wan, Z.-K.3    Tabei, K.4    Mansour, T.S.5
  • 13
    • 70349782205 scopus 로고    scopus 로고
    • Multistep synthesis using modular flow reactors: Bestmann-Ohira reagent for the formation of alkynes and triazoles
    • Baxendale, I. R.; Ley, S. V.; Mansfield, A. C.; Smith, C. D. Multistep synthesis using modular flow reactors: Bestmann-Ohira reagent for the formation of alkynes and triazoles Angew. Chem., Int. Ed. 2009, 48, 4017-4021
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 4017-4021
    • Baxendale, I.R.1    Ley, S.V.2    Mansfield, A.C.3    Smith, C.D.4
  • 14
    • 84877835595 scopus 로고    scopus 로고
    • Click chemistry for drug development and diverse chemical-biology applications
    • Thirumurugan, P.; Matosiuk, D.; Jozwiak, K. Click chemistry for drug development and diverse chemical-biology applications Chem. Rev. 2013, 113, 4905-4979
    • (2013) Chem. Rev. , vol.113 , pp. 4905-4979
    • Thirumurugan, P.1    Matosiuk, D.2    Jozwiak, K.3
  • 16
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective ligation of azides and terminal alkynes
    • Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective ligation of azides and terminal alkynes Angew. Chem., Int. Ed. 2002, 41, 2596-2599
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 17
    • 0037012920 scopus 로고    scopus 로고
    • Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides
    • Tornoe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides J. Org. Chem. 2002, 67, 3057-3064
    • (2002) J. Org. Chem. , vol.67 , pp. 3057-3064
    • Tornoe, C.W.1    Christensen, C.2    Meldal, M.3
  • 18
    • 4444324951 scopus 로고    scopus 로고
    • Polytriazoles as copper(I)-stabilizing ligands in catalysis
    • Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Polytriazoles as copper(I)-stabilizing ligands in catalysis Org. Lett. 2004, 6, 2853-2855
    • (2004) Org. Lett. , vol.6 , pp. 2853-2855
    • Chan, T.R.1    Hilgraf, R.2    Sharpless, K.B.3    Fokin, V.V.4
  • 19
    • 35548939058 scopus 로고    scopus 로고
    • Ligand-accelerated Cu-catalyzed azide-alkyne cycloaddition: A mechanistic report
    • Rodionov, V. O.; Presolski, S. I.; Díaz Díaz, D.; Fokin, V. V.; Finn, M. G. Ligand-accelerated Cu-catalyzed azide-alkyne cycloaddition: A mechanistic report J. Am. Chem. Soc. 2007, 129, 12705-12712
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 12705-12712
    • Rodionov, V.O.1    Presolski, S.I.2    Díaz Díaz, D.3    Fokin, V.V.4    Finn, M.G.5
  • 21
    • 2442698173 scopus 로고    scopus 로고
    • Direct synthesis of 1,5-disubstituted-4-magnesio-1,2,3-triazoles, revisited
    • Krasiński, A.; Fokin, V. V.; Sharpless, K. B. Direct synthesis of 1,5-disubstituted-4-magnesio-1,2,3-triazoles, revisited Org. Lett. 2004, 6, 1237-1240
    • (2004) Org. Lett. , vol.6 , pp. 1237-1240
    • Krasiński, A.1    Fokin, V.V.2    Sharpless, K.B.3
  • 22
    • 77957163768 scopus 로고    scopus 로고
    • Transition-metal-free catalytic synthesis of 1,5-diaryl-1,2,3-triazoles
    • Kwok, S. W.; Fotsing, J. R.; Fraser, R. J.; Rodionov, V. O.; Fokin, V. V. Transition-metal-free catalytic synthesis of 1,5-diaryl-1,2,3-triazoles Org. Lett. 2010, 12, 4217-4219
    • (2010) Org. Lett. , vol.12 , pp. 4217-4219
    • Kwok, S.W.1    Fotsing, J.R.2    Fraser, R.J.3    Rodionov, V.O.4    Fokin, V.V.5
  • 23
    • 17844397956 scopus 로고    scopus 로고
    • Trimethylsilyl-directed 1,3-dipolar cycloaddition reactions in the solid-phase synthesis of 1,2,3-triazoles
    • Coats, S. J.; Link, J. S.; Gauthier, D.; Hlasta, D. Trimethylsilyl- directed 1,3-dipolar cycloaddition reactions in the solid-phase synthesis of 1,2,3-triazoles Org. Lett. 2005, 7, 1469-1472
    • (2005) Org. Lett. , vol.7 , pp. 1469-1472
    • Coats, S.J.1    Link, J.S.2    Gauthier, D.3    Hlasta, D.4
  • 24
    • 80053507454 scopus 로고    scopus 로고
    • Sulfonyl and phosphoryl azides: Going further beyond the click realm of alkyl and aryl azides
    • Kloss, F.; Kohn, U.; Jahn, B. O.; Hager, M. D.; Gorls, H.; Schubert, U. S. Sulfonyl and phosphoryl azides: Going further beyond the click realm of alkyl and aryl azides Chem.-Asian J. 2011, 6, 2816-2634
    • (2011) Chem.-Asian J. , vol.6 , pp. 2816-2634
    • Kloss, F.1    Kohn, U.2    Jahn, B.O.3    Hager, M.D.4    Gorls, H.5    Schubert, U.S.6
  • 25
    • 84900844586 scopus 로고    scopus 로고
    • 3-catalyzed [3 + 2] cycloaddition of azides with nitroolefins: Regioselective synthesis of 1,5-disubstituted 1,2,3-triazoles
    • 3-catalyzed [3 + 2] cycloaddition of azides with nitroolefins: Regioselective synthesis of 1,5-disubstituted 1,2,3-triazoles J. Org. Chem. 2014, 79, 4463-4469
    • (2014) J. Org. Chem. , vol.79 , pp. 4463-4469
    • Wang, Y.1    Xie, Y.2    Qu, H.3    Wang, H.4    Pan, Y.5    Huang, F.6
  • 26
    • 84870247218 scopus 로고    scopus 로고
    • A new method for the synthesis of 1,5-disubstituted 1,2,3-triazoles via triazolium salt intermediates
    • Koguchi, S.; Izawa, K. A new method for the synthesis of 1,5-disubstituted 1,2,3-triazoles via triazolium salt intermediates Synthesis 2012, 44, 3603-3608
    • (2012) Synthesis , vol.44 , pp. 3603-3608
    • Koguchi, S.1    Izawa, K.2
  • 27
    • 0347417134 scopus 로고    scopus 로고
    • Room-temperature ionic liquids. Solvents for synthesis and catalysis
    • Welton, T. Room-temperature ionic liquids. Solvents for synthesis and catalysis Chem. Rev. 1999, 99, 2071-2084
    • (1999) Chem. Rev. , vol.99 , pp. 2071-2084
    • Welton, T.1
  • 28
    • 0000034575 scopus 로고    scopus 로고
    • Ionic liquids-New solutions for transition metal catalysis
    • Wasserscheid, P.; Keim, W. Ionic liquids-New solutions for transition metal catalysis Angew. Chem., Int. Ed. 2000, 39, 3772-3789
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3772-3789
    • Wasserscheid, P.1    Keim, W.2
  • 29
    • 0035824303 scopus 로고    scopus 로고
    • Catalytic reactions in ionic liquids
    • Sheldon, R. A. Catalytic reactions in ionic liquids Chem. Commun. 2001, 2399-2407
    • (2001) Chem. Commun. , pp. 2399-2407
    • Sheldon, R.A.1
  • 30
    • 0036998098 scopus 로고    scopus 로고
    • Applications of ionic liquid in organic synthesis
    • Malhotra, S. V. Applications of ionic liquid in organic synthesis Aldrichim. Acta 2002, 35, 75-83
    • (2002) Aldrichim. Acta , vol.35 , pp. 75-83
    • Malhotra, S.V.1
  • 31
    • 79955884563 scopus 로고    scopus 로고
    • Room-temperature ionic liquids. Solvents for synthesis and catalysis 2
    • Hallett, J. P.; Welton, T. Room-temperature ionic liquids. Solvents for synthesis and catalysis 2 Chem. Rev. 2011, 5, 3508-3576
    • (2011) Chem. Rev. , vol.5 , pp. 3508-3576
    • Hallett, J.P.1    Welton, T.2


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