Triazole: Difference between revisions
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== Chemistry of substituted 1,2,3-triazoles == | == Chemistry of substituted 1,2,3-triazoles == | ||
Most substituted triazoles are synthesized by using one of several click chemistry methods. One method uses paladium catalysts to couple alkenyl halides and sodium azide to product 4-substituted-1,2,3-triazoles<ref>{{cite journal|title=Developments in Pd catalysis: synthesis of 1H-1,2,3-triazoles from sodium azide and alkenyl bromides| | Most substituted triazoles are synthesized by using one of several click chemistry methods. One method uses paladium catalysts to couple alkenyl halides and sodium azide to product 4-substituted-1,2,3-triazoles<ref>{{cite journal|title=Developments in Pd catalysis: synthesis of 1H-1,2,3-triazoles from sodium azide and alkenyl bromides| | ||
author=J. Barluenga, C. Valdes, G. Beltran, M. Esribano, and F. Aznar|journal=Angew. Chem. Int. Ed.|year=2006|volume=45|pages=6893-6896}}</ref>. This reaction also works with aromatic alkenyl halides. Click chemistry between azides and terminal aklynes, catalyzed by various copper reagents, can be used to synthesize 3,5-disubstituted-1,2,3-triazoles<ref>{{cite journal|title=Huisgen 1,3-Dipolar Cycloaddition |author=V.V. Rostovtsev, LG Green, VV Fokin and KB Sharpless|journal=Angew. Chem.|volume=114|year=2002|pages=2708-2711}}</ref>,<ref>{{cite journal|title=Heterogeneous Copper-in-Charcoal-Catalyzed Click Chemistry|author=B.H. Lipshutz, B. R. Taft|journal=Angew. Chem. Int. Ed.|year=2006|volume=45|pages=8235-8238}}</ref>. | author=J. Barluenga, C. Valdes, G. Beltran, M. Esribano, and F. Aznar|journal=Angew. Chem. Int. Ed.|year=2006|volume=45|pages=6893-6896}}</ref>. This reaction also works with aromatic alkenyl halides. Click chemistry between azides and terminal aklynes, catalyzed by various copper reagents, can be used to synthesize 3,5-disubstituted-1,2,3-triazoles<ref>{{cite journal|title=Huisgen 1,3-Dipolar Cycloaddition |author=V.V. Rostovtsev, LG Green, VV Fokin and KB Sharpless|journal=Angew. Chem.|volume=114|year=2002|pages=2708-2711}}</ref>,<ref>{{cite journal|title=Heterogeneous Copper-in-Charcoal-Catalyzed Click Chemistry|author=B.H. Lipshutz, B. R. Taft|journal=Angew. Chem. Int. Ed.|year=2006|volume=45|pages=8235-8238|doi=10.1002/anie.200603726}}</ref>. | ||
[[Image:1,2,3-triazole synthesis substituted.jpg|right|thumb|450px|Triazole synthesis.]] | [[Image:1,2,3-triazole synthesis substituted.jpg|right|thumb|450px|Triazole synthesis.]] | ||
A variety of 1,4-disubstituted-1,2,3-triazoles can be made economically and in an environmentally friendly manner, by reacting a secondary amine, propargyl halides and an azide together in water, under atmospheric oxygen with a copper catalystic.<ref>{{cite journal|title=Efficient synthesis of 1,4-disubstituted 1,2,3-triazoles in ionic liquid/water system|author=Yan, Zhao, Fan, Liu and Liang|journal=Tetrahedron|year=2005|volume=61|pages=9331-9337|doi= | A variety of 1,4-disubstituted-1,2,3-triazoles can be made economically and in an environmentally friendly manner, by reacting a secondary amine, propargyl halides and an azide together in water, under atmospheric oxygen with a copper catalystic.<ref>{{cite journal|title=Efficient synthesis of 1,4-disubstituted 1,2,3-triazoles in ionic liquid/water system|author=Yan, Zhao, Fan, Liu and Liang|journal=Tetrahedron|year=2005|volume=61|pages=9331-9337|doi=10.1016/j.tetlet.2006.01.004}}</ref>. Another method of 1,4-disubstituted-1,2,3-triazoles (not shown) uses no solvent. In this method, the cycloaddition of alkyl azides with enol ethers provides triazoles that are not amendable to synthesis using the coupling of azides with alkynes.<ref>{{cite journal|title=Synthesis of 1,2,3-Triazoles by Cycloadditions of Azides with Enol Ethers|author=D.R. Rogue, J. L. Neill, J. W. Antoon, E. P. Stevens|journal=Synthesis|year=2005|volume=2005|pages=2497-2502|doi=10.1055/s-2005-872116}}</ref> A variety of other synthetic methods are available<ref>{{cite web|url=http://www.organic-chemistry.org/heterocycles/1,2,3-triazoles.shtm|title=1,2,3-triazole synthesis|accessdate=2008-05-17}}</ref>. | ||
Revision as of 11:49, 17 May 2008
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| Uses: | antifungal | ||||||
| Properties: | basic | ||||||
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The triazoles are two isomers, namely 1,2,3-triazole or 1,2,4-triazole, with the formula C2H3N3. They are aromatic ring compounds that are similar to the azoles pyrazole and imidazole, but they would have an additional nitrogen atom in the ring structure. Like the azoles, triazoles are used in many antifungal drugs and fungicides, and the triazole-based drugs are more selective for fungi than mammalian cells compared to the azole-based antifungal compounds. Today, most substituted triazoles are produced by so-called click chemistry pioneered by K. Barry Sharpless and others (see below).
Chemistry of substituted 1,2,3-triazoles
Most substituted triazoles are synthesized by using one of several click chemistry methods. One method uses paladium catalysts to couple alkenyl halides and sodium azide to product 4-substituted-1,2,3-triazoles[1]. This reaction also works with aromatic alkenyl halides. Click chemistry between azides and terminal aklynes, catalyzed by various copper reagents, can be used to synthesize 3,5-disubstituted-1,2,3-triazoles[2],[3].
A variety of 1,4-disubstituted-1,2,3-triazoles can be made economically and in an environmentally friendly manner, by reacting a secondary amine, propargyl halides and an azide together in water, under atmospheric oxygen with a copper catalystic.[4]. Another method of 1,4-disubstituted-1,2,3-triazoles (not shown) uses no solvent. In this method, the cycloaddition of alkyl azides with enol ethers provides triazoles that are not amendable to synthesis using the coupling of azides with alkynes.[5] A variety of other synthetic methods are available[6].
References
- ↑ J. Barluenga, C. Valdes, G. Beltran, M. Esribano, and F. Aznar (2006). "Developments in Pd catalysis: synthesis of 1H-1,2,3-triazoles from sodium azide and alkenyl bromides". Angew. Chem. Int. Ed. 45: 6893-6896.
- ↑ V.V. Rostovtsev, LG Green, VV Fokin and KB Sharpless (2002). "Huisgen 1,3-Dipolar Cycloaddition". Angew. Chem. 114: 2708-2711.
- ↑ B.H. Lipshutz, B. R. Taft (2006). "Heterogeneous Copper-in-Charcoal-Catalyzed Click Chemistry". Angew. Chem. Int. Ed. 45: 8235-8238. DOI:10.1002/anie.200603726. Research Blogging.
- ↑ Yan, Zhao, Fan, Liu and Liang (2005). "Efficient synthesis of 1,4-disubstituted 1,2,3-triazoles in ionic liquid/water system". Tetrahedron 61: 9331-9337. DOI:10.1016/j.tetlet.2006.01.004. Research Blogging.
- ↑ D.R. Rogue, J. L. Neill, J. W. Antoon, E. P. Stevens (2005). "Synthesis of 1,2,3-Triazoles by Cycloadditions of Azides with Enol Ethers". Synthesis 2005: 2497-2502. DOI:10.1055/s-2005-872116. Research Blogging.
- ↑ 1,2,3-triazole synthesis. Retrieved on 2008-05-17.