Download PDF
Synthesis 2012; 44(10): 1577-1583
DOI: 10.1055/s-0031-1290772
paper
© Georg Thieme Verlag Stuttgart · New York

An Efficient One-Pot Synthesis of 3,5-Disubstituted 1H-Pyrazoles

Lei-Lei Wu
a   Key Lab of Green Chemistry and Technology, Ministry of Education, The Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. of China, Fax: +86(28)85412904   Email: scuhchen@scu.edu.cn
,
Yi-Cen Ge
a   Key Lab of Green Chemistry and Technology, Ministry of Education, The Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. of China, Fax: +86(28)85412904   Email: scuhchen@scu.edu.cn
,
Ting He
b   Institute of Chemical Materials, China Academy of Engineering Physics (CAEP), Chengdu, Sichuan 610065, P. R. of China
,
Lei Zhang
a   Key Lab of Green Chemistry and Technology, Ministry of Education, The Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. of China, Fax: +86(28)85412904   Email: scuhchen@scu.edu.cn
,
Xing-Li Fu
c   Guangxi Vocational and Technical Institute of Industry, Nanning, Guangxi 530001, P. R. of China
,
Hai-Yan Fu
a   Key Lab of Green Chemistry and Technology, Ministry of Education, The Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. of China, Fax: +86(28)85412904   Email: scuhchen@scu.edu.cn
,
Hua Chen*
a   Key Lab of Green Chemistry and Technology, Ministry of Education, The Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. of China, Fax: +86(28)85412904   Email: scuhchen@scu.edu.cn
,
Rui-Xiang Li
a   Key Lab of Green Chemistry and Technology, Ministry of Education, The Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. of China, Fax: +86(28)85412904   Email: scuhchen@scu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 01 December 2011

Accepted after revision: 29 February 2012

Publication Date:
19 April 2012 (online)

    Permissions and Reprints All articles of this category


Abstract

An efficient, general, one-pot, three-component procedure for the preparation of 3,5-disubstituted 1H-pyrazoles via condensation of substituted aromatic aldehydes, tosylhydrazine and terminal alkynes in toluene is reported. The reaction tolerates a variety of functional groups and sterically hindered substrates to afford the desired pyrazoles in yields of 67–91%.

Key words

pyrazoles - heterocycles - condensation - cycloaddition - aldehydes

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
  • Supporting Information
 

  • References

    • 1a Qiao JX, Cheng XH, Smallheer JM, Galemmo RA, Drummond S, Pinto D, Cheney DL, He K, Wong PC, Luettgen JM, Knabb RM, Wexler RR, Lam P. Bioorg. Med. Chem. Lett. 2007; 17: 1432
      Crossref
    • 1b Lamberth C. Heterocycles 2007; 71: 1467
      Crossref
    • 1c Singh P, Paul K, Holzer W. Bioorg. Med. Chem. 2006; 14: 5061
      CrossrefPubMed
    • 1d Elguero J. Pyrazoles . In Comprehensive Heterocyclic Chemistry II. Vol. 3. Katritzky AR, Rees CW, Scriven EF. V. Pergamon; Oxford: 1996: 1
      Google Scholar
    • 1e Ache HJ. Angew. Chem. Int. Ed. 1989; 28: 1
    • 1f Elguero J. Pyrazoles and their Benzo Derivatives. In Comprehensive Heterocyclic Chemistry. Vol. 5. Katritzky AR, Rees CW. Pergamon; Oxford: 1984: 167
      Google Scholar
    • 2a Zhu LB, Cheng L, Zhang YX, Xie RG, You JS. J. Org. Chem. 2007; 72: 2737
      CrossrefPubMed
    • 2b Kufelnicki A, Wozniczka M, Checinska L, Miernicka M, Budzisz E. Polyhedron 2007; 26: 2589
      Crossref
    • 2c Ovejero P, Mayoral MJ, Cano M, Lagunas MC. J. Organomet. Chem. 2007; 692: 1690
      Crossref
    • 2d Burling S, Field LD, Messerle BA, Rumble SL. Organometallics 2007; 26: 4335
      Crossref
    • 2e Kealey S, Long NJ, Miller PW, White A, Hitchcock PB, Gee A. Dalton Trans. 2007; 2823
    • 2f Kawatsura M, Aburatani S, Uenishi J. Tetrahedron 2007; 63: 4172
      Crossref
    • 2g Attanasi OA, Berretta S, Crescentini LD, Favi G, Filippone P, Giorgi G, Lillini S, Mantellini F. Tetrahedron Lett. 2007; 48: 2449
      Crossref
    • 2h Cottineau B, Chenault J. Synlett 2002; 769
  • 3 Fustero S, Sánchez-Roselló M, Barrio P, Simón-Fuentes A. Chem. Rev. 2011; 111: 6984
    CrossrefPubMed
    • 4a Heller ST, Natarajan SR. Org. Lett. 2006; 8: 2675
      CrossrefPubMed
    • 4b Xie FC, Cheng G, Hu YH. J. Comb. Chem. 2006; 8: 286
      Crossref
    • 4c Armstrong A, Jones LH, Knight JD, Kelsey RD. Org. Lett. 2005; 7: 713
      CrossrefPubMed
    • 4d Wang ZX, Qin HL. Green Chem. 2004; 6: 90
      Crossref
    • 4e Kost AN, Grandberg II. Advances in Heterocyclic Chemistry . Progress in Pyrazole Chemistry . In Vol. 6. Katritzky AR, Boulton AJ. Academic Press; London: 1966: 347
      Google Scholar
    • 5a Katritzky AR, Wang MY, Zhang SM, Vonkov A, Steel PJ. J. Org. Chem. 2001; 66: 6787
      Crossref
    • 5b Luo Y, Potvin PG. J. Org. Chem. 1994; 59: 1761
      Crossref
    • 5c Murray W, Wachter M, Barton D, Forerokelly Y. Synthesis 1991; 18
      Article in Thieme Connect
  • 6 Outirite M, Lebrini M, Lagrenee M, Bentiss F. J. Heterocycl. Chem. 2008; 45: 503
    Crossref
  • 7 Tufariello JJ In 1,3-Dipolar Cycloaddition Chemistry. Vol. 2. Padwa A. John Wiley & Sons; New York: 1984: 83
    Google Scholar
    • 8a Jiang N, Li C. Chem. Commun. 2004; 394
    • 8b Qi X, Ready JM. Angew. Chem. Int. Ed. 2007; 3242
    • 8c Vuluga D, Legros J, Crousse B, Bonnet-Delpon D. Green Chem. 2009; 11: 156
      Crossref
    • 9a Chandanshive JZ, Bonini F, Gentili D, Fochi M, Bernardi L, Franchini MC. Eur. J. Org. Chem. 2010; 6440
    • 9b Fuchi N, Doi T, Takahasi T. Chem. Lett. 2005; 438
    • 9c Abunada NM, Hassaneen HM, Kandile NG, Miqdad OA. Molecules 2008; 1501
    • 9d Bonini BF, Franchini MC, Gentili D, Locatelli E, Ricci A. Synlett 2009; 2328
      Article in Thieme Connect
  • 10 Aggarwal VK, de Vicente J, Bonnert RV. J. Org. Chem. 2003; 68: 5381
    Crossref
  • 11 Creary X. Org. Synth. 1986; 64: 207
    • 12a Aggarwal VK, Alonso E, Hynd G, Lydon KM, Palmer MJ, Porcelloni M, Studley JR. Angew. Chem. Int. Ed. 2001; 40: 1430
      Crossref
    • 12b Aggarwal VK, Alonso E, Fang GY, Ferrara M, Hynd G, Porcelloni M. Angew. Chem. Int. Ed. 2001; 40: 1433
      Crossref
    • 12c Aggarwal VK, Fulton JR, Sheldon CG, de Vicente J. J. Am. Chem. Soc. 2003; 125: 6034
      CrossrefPubMed
    • 12d Aggarwal VK, de Vicente J, Bonnert RV. Org. Lett. 2001; 3: 2785
      CrossrefPubMed
    • 12e Velikorodov AV, Kovalev VB, Krivosheev OO. Russ. J. Org. Chem. 2009; 45: 1208
      Crossref
    • 12f Aggarwal VK, de Vicente J, Pelotier B, Holmes IP, Bonnert RV. Tetrahedron Lett. 2000; 41: 10327
      Crossref
  • 13 Li P, Zhao J, Wu C, Larock RC, Shi F. Org. Lett. 2011; 13: 3340
    CrossrefPubMed
  • 14 Barluenga J, Tomas-Gamasa M, Aznar F, Valdes C. Nat. Chem. 2009; 1: 494
    Crossref
    • 15a Wang D, Fan L, Zheng C, Fang Z. J. Fluorine Chem. 2010; 131: 584
      Crossref
    • 15b Shaw AY, Liau H, Lu P, Yang C, Lee C, Chen J, Xu Z, Flynn G. Bioorg. Med. Chem. 2010; 18: 3270
      Crossref
  • 16 Huang XQ, Dou JM, Li DC, Wang DQ. J. Chil. Chem. Soc. 2009; 54: 20
  • 17 Rohit D. J. Pharm. Res. 2011; 10: 6
  • 18 Ren ZJ, Cao WG, Chen J, Wang Y, Ding WY. J. Heterocycl. Chem. 2006; 43: 495
    Crossref
  • 19 Sharma JP. Pestic. Res. J. 2006; 18: 7
  • 20 Soliman EA. Egypt. J. Chem. 1981; 23: 75
  • 21 Liu HL, Jiang HF, Zhang M, Yao WJ, Zhu QH, Tang Z. Tetrahedron Lett. 2008; 49: 3805
    Crossref
  • 22 Volkov AN. Zh. Org. Khim. 1978; 14: 938