Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2018; 50(11): 2191-2199
DOI: 10.1055/s-0036-1591557
DOI: 10.1055/s-0036-1591557
paper
CuI/Et2NH-Catalyzed One-Pot Highly Efficient Synthesis of 1,4-Disubstituted 1,2,3-Triazoles in Green Solvent Glycerol
This research was supported by College of Chemistry and Chemical Engineering, Henan University, and Institute of Chemistry Co. Ltd., Henan Academy of Sciences.Further Information
Publication History
Received: 04 January 2018
Accepted after revision: 27 February 2018
Publication Date:
28 March 2018 (online)
![](https://www.thieme-connect.de/media/synthesis/201811/lookinside/thumbnails/ss-2018-h0700-op_10-1055_s-0036-1591557-1.jpg)
Abstract
A concise one-pot three-component reaction of organic halides, terminal acetylenes, and sodium azide provided an efficient route for the synthesis of 1,2,3-triazoles. A variety of 1,2,3-triazoles were prepared in good to excellent yields with green solvent glycerol. This procedure used CuI and diethylamine, which are two easily available reagents as the new catalytic system at room temperature.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591557.
- Supporting Information
-
References
- 1a Horne WS. Yadav MK. Stout CD. Ghadiri MR. J. Am. Chem. Soc. 2004; 126: 15366
- 1b Pagliai F. Pirali T. Grosso ED. Brisco RD. Tron GC. Sorba G. Genaz-zani AA. J. Med. Chem. 2006; 49: 467
- 1c Angell YL. Burgess K. Chem. Soc. Rev. 2007; 36: 1674
- 1d Meldal M. Tornoe CW. Chem. Rev. 2008; 108: 2952
- 2a Bock VD. Speijer D. Hiemstra H. van Maarseveen JH. Org. Biomol. Chem. 2007; 5: 971
- 2b Dedola S. Nepogodiev SA. Field RA. Org. Biomol. Chem. 2007; 5: 1006
- 3a Wu P. Feldman AK. Nugent AK. Hawker CJ. Scheel A. Voit B. Pyun J. Fréchet JM. J. Sharpless KB. Fokin VV. Angew. Chem. Int. Ed. 2004; 43: 3928
- 3b Nandivada H. Jiang XW. Lahann J. Adv. Mater. 2007; 19: 2197
- 3c Johnson TC. Totty WG. Wills M. Org. Lett. 2012; 14: 5230
- 4a Kolb HC. Sharpless KB. Drug. Discov. Today 2003; 8: 1128
- 4b Sugawara A. Sunazuka T. Hirose T. Nagai K. Yamaguchi Y. Hanaki H. Sharpless KB. Omura S. Bioorg. Med. Chem. Lett. 2007; 17: 6340
- 4c Tron GC. Pirali T. Billington RA. Canonico PL. Sorba G. Genazzani AA. Med. Res. Rev. 2008; 28: 278
- 5a Dai Q. Gao W. Liu D. Kapzes LM. Zhang X. J. Org. Chem. 2006; 71: 3928
- 5b Liu YX. Yan WM. Chen YF. Petersen JL. Shi XD. Org. Lett. 2008; 10: 5389
- 6a Meldal M. Christensen CC. Tornøe W. J. Org. Chem. 2002; 67: 3057
- 6b Li Z. Seo TS. Ju J. Tetrahedron Lett. 2004; 45: 3143
- 6c Zhang L. Chen X. Xue P. Sun HH. Y. Williams ID. Sharpless KB. Fokin VV. Jia G. J. Am. Chem. Soc. 2005; 127: 15998
- 6d Golas PL. Tsarevsky NV. Sumerlin BS. Matyjaszewski K. Macromolecules. 2006; 39: 6451
- 6e Kwok SW. Fotsing JR. Fraser RJ. Rodionov VO. Fokin VV. Org. Lett. 2010; 12: 4217
- 7a Kolb HC. Finn MG. Sharpless KB. Angew. Chem. Int. Ed. 2001; 40: 2004
- 7b Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
- 7c Rodionov VO. Fokin VV. Finn MG. Angew. Chem. Int. Ed. 2005; 44: 2210
- 7d Debets MF. van Berkel SS. Dommerholt J. Dirks AJ. Rutjes FP. J. T. van Delft FL. Acc. Chem. Res. 2011; 44: 805
- 8 Scriven EF. V. Turnbull K. Chem. Rev. 1988; 88: 297
- 9a Feldman AK. Colasson B. Fokin VV. Org. Lett. 2004; 6: 3897
- 9b Baig RB. N. Varma RS. Chem. Commun. 2012; 48: 5853
- 9c Mukherjee N. Ahammed S. Bhadra S. Ranu BC. Green Chem. 2013; 15: 389
- 9d Wei F. Li H. Song C. Ma Y. Zhou L. Tung C. Xu Z. Org. Lett. 2015; 17: 2860
- 10a Liu PN. Siyang HX. Zhang L. San Tse SK. Jia G. J. Org. Chem. 2012; 77: 5844
- 10b Ali A. Correa AG. Alves D. Zukerman-Schpector J. Westermann B. Ferreira MA. B. Paixao MW. Chem. Commun. 2014; 50: 11926
- 10c Shil AK. Kumar S. Sharma S. Chaudhary A. Das P. RSC Adv. 2015; 5: 11506
- 11 Capello C. Fisher U. Kungerbühler K. Green Chem. 2007; 9: 927
- 12 Radatz CS. Soares LA. Vieira ER. Alves D. Russowsky D. Schneider PH. New J. Chem. 2014; 38: 1410
- 13 Tasca E. Sorella G. Sperni L. Strukul G. Scarso A. Green Chem. 2015; 17: 1414
- 14 Alonso F. Moglie Y. Radivoy G. Yus M. J. Org. Chem. 2011; 76: 8394
- 15a DeSimone JM. Science 2002; 297: 799
- 15b Nelson WM. Green Solvents for Chemistry: Perspectives and Practice . Oxford University Press; New York: 2003
- 15c Clark JH. Taverner SJ. Org. Process Res. Dev. 2007; 11: 149
- 16a Gu Y. Barrault J. Jérôme F. Adv. Synth. Catal. 2008; 350: 2007
- 16b Gu Y. De Sousa R. Frapper G. Bachmann C. Barrault J. Jéřome F. Green Chem. 2009; 11: 1968
For selected examples:
For selected examples:
For selected examples:
For selected examples, see ref. 1d and:
For selected examples:
For selected examples, see ref. 1d and:
For selected examples:
For selected examples:
For selected examples: