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Volumn , Issue 16, 2008, Pages 2603-2609

Reactions of unsaturated azides; Part 22:1 The alkyne azide click chemistry as a synthetic tool for the generation of cage-like triazole compounds

Author keywords

Alkynes; Azides; Click chemistry; Cycloadditions; Triazoles

Indexed keywords

CHLORINE COMPOUNDS; COPPER;

EID: 50849100151     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078602     Document Type: Article
Times cited : (11)

References (68)
  • 7
    • 0037012920 scopus 로고    scopus 로고
    • Independently of Sharpless and co-workers, Tornøe, Christensen, and Meldal introduced the copper(I)-catalyzed regioselective 1,3-dipolar cycloaddition of terminal alkynes at azides in the solid-phase synthesis at nearly the same time: Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
    • Independently of Sharpless and co-workers, Tornøe, Christensen, and Meldal introduced the copper(I)-catalyzed regioselective 1,3-dipolar cycloaddition of terminal alkynes at azides in the solid-phase synthesis at nearly the same time: Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
  • 9
    • 0013064237 scopus 로고    scopus 로고
    • Angew. Chem. 2002, 114, 2708.
    • (2002) Angew. Chem , vol.114 , pp. 2708
  • 10
    • 17644414186 scopus 로고    scopus 로고
    • For kinetic investigations on the reaction mechanism, see
    • For kinetic investigations on the reaction mechanism, see: Rodionov, V. O.; Fokin, V. V.; Finn, M. G. Angew. Chem. Int. Ed. 2005, 44, 2210;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 2210
    • Rodionov, V.O.1    Fokin, V.V.2    Finn, M.G.3
  • 11
    • 17644394395 scopus 로고    scopus 로고
    • Angew. Chem. 2005, 117, 2250.
    • (2005) Angew. Chem , vol.117 , pp. 2250
  • 13
    • 50849131843 scopus 로고    scopus 로고
    • The copper(I) catalysis works well in a broad pH range, tolerates a large number of several functional groups, and is insensitive against water and oxygen. The reaction is regioselective and leads to products, which can be easily isolated: Durán Pachón, L.; van Maarseveen, J. H.; Rothenberg, G. Adv. Synth. Catal. 2005, 347, 811.
    • The copper(I) catalysis works well in a broad pH range, tolerates a large number of several functional groups, and is insensitive against water and oxygen. The reaction is regioselective and leads to products, which can be easily isolated: Durán Pachón, L.; van Maarseveen, J. H.; Rothenberg, G. Adv. Synth. Catal. 2005, 347, 811.
  • 15
    • 50849103902 scopus 로고    scopus 로고
    • Angew. Chem. 2001, 113, 2056.
    • (2001) Angew. Chem , vol.113 , pp. 2056
  • 19
    • 36749078020 scopus 로고    scopus 로고
    • Angew. Chem. 2007, 119, 2147.
    • (2007) Angew. Chem , vol.119 , pp. 2147
  • 29
    • 84943402961 scopus 로고
    • Katritzky, A. R, Rees, C. W, Eds, Pergamon: Oxford
    • (f) Wamhoff, H. In Comprehensive Heterocyclic Chemistry, Vol. 5; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984, 669.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.5 , pp. 669
    • Wamhoff, H.1
  • 36
    • 0000309936 scopus 로고    scopus 로고
    • Angew. Chem. 2002, 114, 1095.
    • (2002) Angew. Chem , vol.114 , pp. 1095
  • 38
    • 33645598262 scopus 로고    scopus 로고
    • Angew. Chem. 2005, 117, 118.
    • (2005) Angew. Chem , vol.117 , pp. 118
  • 41
    • 35348874833 scopus 로고    scopus 로고
    • Angew. Chem. 2007, 119, 1036.
    • (2007) Angew. Chem , vol.119 , pp. 1036
  • 44
    • 14744291643 scopus 로고    scopus 로고
    • Angew. Chem. 2004, 116, 4018.
    • (2004) Angew. Chem , vol.116 , pp. 4018
  • 57
    • 24044531286 scopus 로고    scopus 로고
    • Energy-rich organic azides with low molecular weight, especially those with more than one azido group are potentially explosive and must be handled with care! Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem. Int. Ed. 2005, 44, 5188;
    • Energy-rich organic azides with low molecular weight, especially those with more than one azido group are potentially explosive and must be handled with care! Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem. Int. Ed. 2005, 44, 5188;
  • 58
    • 27944494395 scopus 로고    scopus 로고
    • Angew. Chem. 2005, 117, 5320.
    • (2005) Angew. Chem , vol.117 , pp. 5320
  • 59
    • 0010325122 scopus 로고    scopus 로고
    • The azide 1 was not prepared analogously to the literature given below in order to avoid the isolation of the N-lost compound: (a) Witucki, E. F.; Wilson, E. R.; Flanagan, J. E.; Frankel, M. B. J. Chem. Eng. Data 1983, 28, 285.
    • The azide 1 was not prepared analogously to the literature given below in order to avoid the isolation of the N-lost compound: (a) Witucki, E. F.; Wilson, E. R.; Flanagan, J. E.; Frankel, M. B. J. Chem. Eng. Data 1983, 28, 285.
  • 63
    • 50849120354 scopus 로고
    • Chem. Abstr. 1990, 113, 23050g.
    • (1990) Chem. Abstr , vol.113
  • 65
    • 50849114464 scopus 로고    scopus 로고
    • -1, F(000) = 488. Crystallographic data for the structure reported in this paper have been deposited at the Cambridge Crystallographic Data Centre under the number CCDC 673760. Copies of the data may be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44 1223 33603 or e-mail: deposit@ccdc.cam.ac.uk).
    • -1, F(000) = 488. Crystallographic data for the structure reported in this paper have been deposited at the Cambridge Crystallographic Data Centre under the number CCDC 673760. Copies of the data may be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44 1223 33603 or e-mail: deposit@ccdc.cam.ac.uk).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.