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Synthesis 2015; 47(15): 2281-2284
DOI: 10.1055/s-0034-1380658
DOI: 10.1055/s-0034-1380658
paper
Facile Synthesis of 1-Arylpyrazoles
Further Information
Publication History
Received: 07 February 2015
Accepted after revision: 26 March 2015
Publication Date:
06 May 2015 (online)
Abstract
A convenient and transition-metal-free synthesis of 1-arylpyrazoles that involves the cycloaddition of 3-arylsydnones and acrylic acid is presented. The process proceeds smoothly to obtain the target products with moderate to high yields.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-34-1380658.
- Supporting Information
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References
- 1 Lien JC, Huang LJ, Wang JP, Teng CM, Lee KH, Kuo SC. Bioorg. Med. Chem. 1997; 5: 2111
- 2 Bekhit AA, Abdel-Aziem T. Bioorg. Med. Chem. 2004; 12: 1935
- 3 Ryu CK, Song EH, Shim JY, You HJ, Choi KU, Choi IH, Lee EY, Chae MJ. Bioorg. Med. Chem. Lett. 2003; 13: 17
- 4 Vishnu KT, Dharmendra BY, Ashok KC, Praveen KS. Bioorg. Med. Chem. Lett. 2005; 15: 3288
- 5 Monnier F, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 6954
- 6a Penning TD, Talley JJ, Bertenshaw SR, Carter JS, Collins PW, Docter S, Graneto MJ, Lee LF, Malecha JW, Miyashiro JM, Rogers RS, Rogier DJ, Yu SS, Anderson GD, Burton EG, Cogburn JN, Gregory SA, Koboldt CM, Perkins WE, Seibert K, Veenhuizen AW, Zhang YY, Isakson PC. J. Med. Chem. 1997; 40: 1347
- 6b Kujubu DA, Fletcher BS, Varnum BC, Lim RW, Herschman HR. J. Biol. Chem. 1991; 266: 12866
- 7 Sun X, Tian J, Zhu M, Chai B, Liu C. Agrochemicals 2011; 50: 781
- 8a Taillefer M, Xia N, Ouali A. Angew. Chem. Int. Ed. 2007; 46: 934
- 8b Correa A, Bolma C. Adv. Synth. Catal. 2007; 349: 2673
- 8c Chen W, Zhang Y, Zhu L, Lan J, Xie R, You J. J. Am. Chem. Soc. 2007; 129: 13879
- 8d Suresh P, Pitchumani K. J. Org. Chem. 2008; 73: 9121
- 8e Guo D, Huang H, Xu J, Jiang H, Liu H. Org. Lett. 2008; 10: 4513
- 8f Kaddouri H, Vicente V, Ouali A, Ouazzani F, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 333
- 8g Larsson P, Correa A, Carril M, Norrby P, Bolm C. Angew. Chem. Int. Ed. 2009; 48: 5691
- 8h Swapna K, Kumar AV, Reddy VP, Rao KR. J. Org. Chem. 2009; 74: 7514
- 8i Murthy SN, Madhav B, Reddy VP, Nageswar YV. D. Adv. Synth. Catal. 2010; 352: 3241
- 8j Cano R, Ramon DJ, Yus M. J. Org. Chem. 2011; 76: 654
- 8k Yang K, Qiu Y, Li Z, Wang Z, Jiang S. J. Org. Chem. 2011; 76: 3151
- 8l Huang Z, Li F, Chen B, Xue F, Chen G, Yuan G. Appl. Catal., A 2011; 403: 104
- 8m Cristau H, Cellier PP, Spindler J, Taillefer M. Chem. Eur. J. 2004; 10: 5607
- 9a Finar IL, Godfrey KE. J. Chem. Soc. 1954; 2293
- 9b Guo C, Ren T, Wang J, Li C, Song J. J. Porphyrins Phthalocyanines 2005; 9: 430
- 9c Ju Y, Varma RS. J. Org. Chem. 2006; 71: 135
- 10 Patel HV, Vyas KA, Pandey SP, Tavares F, Fernandes PS. Synlett 1991; 483
- 11a Huisgen R, Gotthardt H, Grashey R. Chem. Ber. 1968; 101: 536
- 11b Huisgen R, Grashey R, Gotthardt H. Chem. Ber. 1968; 101: 829
- 12a Gonzalez-Nogal AM, Calle M, Cuadrado P, Valero R. Tetrahedron 2007; 63: 224
- 12b Browne DL, Vivat JF, Plant A, Gomez-Bengoa E, Harrity JP. A. J. Am. Chem. Soc. 2009; 131: 7762
- 13a Rai NS, Kalluraya B, Lingappa B, Shenoy S, Puranic VG. Eur. J. Med. Chem. 2008; 43: 1715
- 13b Asundaria ST, Patel NS, Patel KC. Org. Commun. 2010; 3: 30
- 13c Fang Y, Wu C, Larock RC, Shi F. J. Org. Chem. 2011; 76: 8840
- 14 Teo Y, Yong F, Lim GS. Tetrahedron Lett. 2011; 52: 7171
- 15 Cristau H, Cellier PP, Spindler J, Taillefer M. Eur. J. Org. Chem. 2004; 695