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
Download PDF
Synthesis 2012; 44(21): 3353-3360
DOI: 10.1055/s-0032-1316783
DOI: 10.1055/s-0032-1316783
paper
Microwave-Assisted Click Chemistry Synthesis of 1,2,3-Triazoles from Aryldiazonium Silica Sulfates in Water
Authors
Further Information
Publication History
Received: 26 June 2012
Accepted after revision: 31 August 2012
Publication Date:
12 September 2012 (online)
Abstract
A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles is studied by in situ generation of aryl azides via the reaction of aryldiazonium silica sulfates and sodium azide, followed by coupling with a terminal alkyne in the presence of copper catalyst. These reactions are carried out in water under mild and heterogeneous conditions without using any additional ligands.
-
References
- 1a Huisgen R, Padwa A. 1,3-Dipolar Cycloaddition Chemistry . Wiley; New York: 1984
- 1b Huisgen R. Pure Appl. Chem. 1989; 61: 613
- 1c Meldal M, Christensen C, Tornoe CW. J. Org. Chem. 2002; 67: 3057
- 1d Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
Reference Ris Wihthout Link
- 1e Meldal M, Tornoe CW. Chem. Rev. 2008; 108: 2952
Reference Ris Wihthout Link
- 2a Kolb HC, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2001; 40: 2004
- 2b Gil MV, Arevalo MJ, Lopez O. Synthesis 2007; 1589
- 3a Krasiski A, Radi Z, Manetsch R, Raushel J, Taylor P, Sharpless KB, Kolb HC. J. Am. Chem. Soc. 2005; 127: 6686
- 3b Suijkerbuijk BM. J. M, Aerts BN. H, Dijkstra HP, Lutz M, Spek AL, Koten GV, Gebbink RJ. M. K. Dalton Trans. 2007; 1273
- 3c Binder WH, Kluger C. Curr. Org. Chem. 2006; 10: 1791
- 3d Hawker CJ, Fokin VV, Finn MG, Sharpless KB. Aust. J. Chem. 2007; 60: 381
- 3e Lutz J.-F. Angew. Chem. Int. Ed. 2007; 46: 1018
- 3f Qvortrup K, Nielsen TE. Chem. Commun. 2011; 47: 3278
- 3g Rathwell K, Sperry J, Brimble MA. Tetrahedron 2010; 66: 4002
- 3h Click Chemistry for Biotechnology and Materials Science. Lahann J. Wiley; Hoboken: 2009
- 4a Alvarez R, Velazquez S, San-Felix A, Aquara S, De Clercq ES, Perno CF, Karlsson A, Balzarini J, Camarasa MJ. J. Med. Chem. 1994; 37: 4185
- 4b Whiting M, Muldoon J, Lin YC, Silverman SM, Lindstrom W, Olson AJ, Kolb HC, Finn MG, Sharpless KB, Elder JH, Fokin VV. Angew. Chem. Int. Ed. 2006; 45: 1435
- 5a Buckle DR, Rockell CJ. M, Smith H, Spicer BA. J. Med. Chem. 1986; 29: 2262
- 5b Buckle DR, Outred DJ, Rockell CJ. M, Smith H, Spicer BA. J. Med. Chem. 1983; 26: 251
- 5c Buckle DR, Rockell CJ. M. J. Chem. Soc., Perkin Trans. 1 1982; 627
- 6 Olesen PH, Sorensen AR, Urso B, Kurtzhals P, Bowler AN, Ehrbar U, Hansen BF. J. Med. Chem. 2003; 46: 3333
- 7 Vicentini CB, Brandolini V, Guarneri M, Giori P. Farmaco 1992; 47: 1021
- 8 Genin MJ, Allwine DA, Anderson DJ, Barbachyn MR, Emmert DE, Garmon SA, Graber DR, Grega KC, Hester JB, Hutchinson DK, Morris J, Reischer RJ, Ford CW, Zurenko GE, Hamel JC, Schaadt RD, Stapert D, Yagi BH. J. Med. Chem. 2000; 43: 953
- 9a Kolb HC, Sharpless KB. Drug Discovery Today 2003; 8: 1128
- 9b Moses JE, Moorhouse AD. Chem. Soc. Rev. 2007; 36: 1249
- 9c Tron GC, Pirali T, Billington RA, Canonico PL, Sorba G, Genazzani AA. Med. Res. Rev. 2008; 28: 278
- 9d Aragao-Leoneti V, Campo VL, Gomes AS, Field RA, Carvalho I. Tetrahedron 2010; 66: 9475
- 9e Norgren AS, Budke C, Majer Z, Heggemann C, Koop T, Sewald N. Synthesis 2009; 488
- 9f Kamal A, Shankaraiah N, Reddy CR, Prabhakar S, Markandeya N, Srivastava HK, Sastry GN. Tetrahedron 2010; 66: 5498
- 10a Petrini M, Shaikh RR. Synthesis 2009; 3143
- 10b Dururgkar AK, Gonnade RG, Ramana CV. Tetrahedron 2009; 65: 3974
- 10c Campbell-Verduyn LS, Mirfeizi L, Dierckx RA, Elsing PH, Feringa BL. Chem. Commun. 2009; 2139
- 10d Huang Y, Gard GL, Shreeve JM. Tetrahedron Lett. 2010; 51: 6951
- 11a Meldal M, Christensen C, Tornoe CW. J. Org. Chem. 2002; 67: 3057
- 11b Kumar B, Reddy VB. Synthesis 2010; 1687
- 11c Conte ML, Grotto D, Chambery A, Dondonia A, Marra A. Chem. Commun. 2011; 47: 1240
- 12a Diez-Gonzalez S, Nolan SP. Angew. Chem. Int. Ed. 2008; 47: 8881
- 12b Wang D, Li N, Zhao M, Shi W, Ma C, Chen B. Green Chem. 2010; 12: 2120
- 12c Straub BF. Chem. Commun. 2007; 3868
- 12d Moore E, McInnes SJ, Vogt A, Voelcker NH. Tetrahedron Lett. 2011; 52: 3227
- 12e Jiang Y, Kuang C, Yang Q. Synlett 2009; 3163
- 12f Chattopadhyay B, Rivera VeraC. I, Chuprakov S, Gevorgyan V. Org. Lett. 2010; 12: 2166
Reference Ris Wihthout Link
- 13a Alonso F, Moglie Y, Radivoy G, Yus M. Eur. J. Org. Chem. 2010; 1875
- 13b Alonso F, Moglie Y, Radivoy G, Yus M. Tetrahedron Lett. 2009; 50: 2358
- 13c Alonso F, Moglie Y, Radivoy G, Yus M. Org. Biomol. Chem. 2011; 9: 6385
- 13d Sarkar A, Mukherjee T, Kapoor S. J. Phys. Chem. C 2008; 112: 3334
- 14a Li P, Wang L, Zhang Y. Tetrahedron 2008; 64: 10825
- 14b Sirion U, Bae YJ, Lee BS, Chi DY. Synlett 2008; 2326
- 14c Chassaing S, Sido AS. S, Alix A, Kumarraja M, Pale P, Sommer J. Chem.–Eur. J. 2008; 14: 6713
- 14d Miao T, Wang L. Synthesis 2008; 363
- 14e Lipshutz BH, Taft BR. Angew. Chem. Int. Ed. 2006; 45: 8235
- 15a Fletcher JT, Reilly JE. Tetrahedron Lett. 2011; 52: 5512
- 15b Yan J, Wang L. Synthesis 2010; 447
- 15c Barral K, Moorhouse AD, Moses JE. Org. Lett. 2007; 9: 1809
- 15d Odlo K, Hoydahl EA, Hansen TV. Tetrahedron Lett. 2007; 48: 2097
- 15e Feldman AK, Colasson B, Fokin VV. Org. Lett. 2004; 6: 3897
- 15f Smith NM, Greaves MJ, Jewell R, Perry MV. D, Stocks MJ, Stonehouse JP. Synthesis 2009; 1391
- 16a Moorhouse AD, Moses JE. Synlett 2008; 2089
- 16b Beckmann HS. G, Wittmann V. Org. Lett. 2007; 9: 1
- 16c Appukkuttan P, Van der Eycken E. Eur. J. Org. Chem. 2008; 1133
- 16d Sreedhar B, Reddy PS. Synth. Commun. 2007; 37: 805
- 16e Appukkuttan P, Dehaen W, Fokin VV, Van der Eycken E. Org. Lett. 2004; 6: 4223
- 17a Zarei A, Hajipour AR, Khazdooz L, Mirjalili BF, Najafichermahini A. Dyes Pigm. 2009; 81: 240
- 17b Zarei A, Hajipour AR, Khazdooz L. Synthesis 2009; 941
- 17c Zarei A, Hajipour AR, Khazdooz L, Aghaei H. Tetrahedron Lett. 2009; 50: 4443
- 17d Zarei A, Hajipour AR, Khazdooz L, Aghaei H. Synlett 2010; 1201
- 17e Zarei A, Khazdooz L, Hajipour AR, Aghaei H. Dyes Pigm. 2011; 91: 44
- 17f Zarei A, Khazdooz L, Pirisedigh A, Hajipour AR, Seyedjamali H, Aghaei H. Tetrahedron Lett. 2011; 52: 4554
- 17g Zarei A, Khazdooz L, Hajipour AR, Rafiee F, Azizi G, Abrishami F. Tetrahedron Lett. 2012; 53: 406
- 17h Pirisedigh A, Zarei A, Seyedjamali H, Khazdooz L, Hajipour AR. Monatsh. Chem. 2012; 143: 791
- 18a Zollinger H In The Chemistry of Amino, Nitroso, Nitro and Related Groups. Patai S. Wiley; New York: 1996
- 18b Olah GA, Laali KK, Wang Q, Prakash GK. S. Onium Ions . Wiley; New York: 1998
- 18c Tour JM. J. Org. Chem. 2007; 72: 7477
- 18d Hubbard A, Okazaki T, Laali KK. J. Org. Chem. 2008; 73: 316
- 18e Fabrizi G, Goggiamani A, Sferrazza A, Cacchi S. Angew. Chem. Int. Ed. 2010; 49: 4067
Reference Ris Wihthout Link
- 18f Felpin FX, Nassar-Hardy L, Callonnec FL, Fouquet E. Tetrahedron 2011; 67: 2815
- 19 Filimonov VD, Trusova M, Postnikov P, Krasnokutskaya EA, Lee YM, Hwang HY, Kim H, Chi KW. Org. Lett. 2008; 10: 3961
- 20a Barbero M, Degani I, Dughera S, Fochi R. Synthesis 2004; 2386
- 20b Krasnokutskaya EA, Semenischeva NI, Filimonov VD, Knochel P. Synthesis 2007; 81
- 20c Gorlushko DA, Filimonov VD, Krasnokutskaya EA, Semenischeva NI, Go BS, Hwang HY, Cha EH, Chi KW. Tetrahedron Lett. 2008; 48: 1080
- 20d Lee YM, Moon MU, Vajpayee V, Filimonov VD, Chi KW. Tetrahedron 2010; 66: 7418
- 21 Taylor JG, Moro AV, Correia CR. D. Eur. J. Org. Chem. 2011; 1403
- 22 Sakamoto T, Uchiyama D, Kondo Y, Yamanaka H. Heterocycles 1993; 35: 1273
- 23a Alonso F, Moglie Y, Radivoy G, Yus M. Heterocycles 2012; 84: 1033
- 23b Alonso F, Moglie Y, Radivoy G, Yus M. J. Org. Chem. 2011; 76: 8394
- 23c Alonso F, Moglie Y, Radivoy G, Yus M. Adv. Synth. Catal. 2010; 76: 3208
- 23d Garcia-Alvarez J, Diez J, Gimeno J. Green Chem. 2010; 12: 2127
- 23e Diez-Gonzalez S, Correa A, Cavallo L, Nolan SP. Chem.–Eur. J. 2006; 12: 7558
- 23f Diez-Gonzalez S, Nolan SP. Angew. Chem. Int. Ed. 2008; 47: 8881
- 23g Diez-Gonzalez S, Stevens ED, Nolan SP. Chem. Commun. 2008; 4747
- 23h Ozcubuku S, Ozkal E, Jimeno C, Pericas MA. Org. Lett. 2009; 11: 4680
- 23i Candelon N, Lasteroueres D, Diallo AK, Ruiz Aranzaes J, Astruc D, Vincent J.-M. Chem. Commun. 2008; 741
- 24 Clark JH. Catalysis of Organic Reactions by Supported Inorganic Reagents. VCH; Weinheim: 1994