Synthesis 2016; 48(04): 541-546
DOI: 10.1055/s-0035-1560553
paper
© Georg Thieme Verlag Stuttgart · New York

Iodine-Mediated Synthesis of Novel Pyrazole Derivatives

Mohammad Mahdavi
a  Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran   Email: ashafiee@ams.ac.ir
,
Mahsa Khoshbakht
b  Department of Chemistry, Imam Khomeini International University, Qazvin, Iran
,
Mina Saeedi
c  Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
d  Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran
,
Mehdi Asadi
a  Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran   Email: ashafiee@ams.ac.ir
,
Mohammad Bayat
b  Department of Chemistry, Imam Khomeini International University, Qazvin, Iran
,
Alireza Foroumadi
a  Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran   Email: ashafiee@ams.ac.ir
,
Abbas Shafiee*
a  Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran   Email: ashafiee@ams.ac.ir
› Author Affiliations
Further Information

Publication History

Received: 30 September 2015

Accepted after revision: 09 November 2015

Publication Date:
07 January 2016 (online)


Abstract

The reaction between N,2-diarylhydrazinecarbothioamide (generated from arylhydrazines and aryl isothiocyanates) and malononitrile in the presence of iodine/triethylamine in N,N-dimethylform­amide at 80 °C afforded novel pyrazoles, 5-amino-1-aryl-3-(arylamino)-1H-pyrazole-4-carbonitriles, in good yields. In this strategy, iodine served as a versatile desulfurizing agent, efficiently promoting the cyclization reaction.

Supporting Information

 
  • References

  • 1 Tekale SU, Kauthale SS, Dake SA, Sarda SR, Pawar RP. Curr. Org. Chem. 2012; 16: 1485
  • 2 Moulay S. Des. Monomers Polym. 2014; 17: 501
  • 3 Rahimizadeh M, Bakavoli M, Shiri A, Eshghi H. Bull. Korean Chem. Soc. 2009; 30: 1699
  • 4 Das B, Krishnaiah M, Venkateswarlu K, Reddy VS. Tetrahedron Lett. 2007; 48: 81
  • 5 Sun J, Dong Y, Cao L, Wang X, Wang S, Hu Y. J. Org. Chem. 2004; 69: 8932
  • 6 Gao S, Tzeng T, Sastry MN. V, Chu CM, Liu JT, Lin C, Yao C.-F. Tetrahedron Lett. 2006; 47: 1889
  • 7 Yadav JS, Reddy BV. S, Chaya DN, Kumar GG. K. S. N, Aravind S, Kunwar AC, Madavi C. Tetrahedron Lett. 2008; 49: 3330
  • 8 Mori N, Togo H. Tetrahedron 2005; 61: 5915
    • 9a Shibahara F, Kitagawa A, Yamaguchi E, Murai T. Org. Lett. 2006; 8: 5621
    • 9b Yella R, Khatun N, Rout SK, Patel BK. Org. Biomol. Chem. 2011; 9: 3235
    • 9c Nath J, Patel BK, Jamir L, Sinha UB, Satyanarayana KV. V. V. Green Chem. 2009; 11: 1503
  • 10 Küçükgüzel ŞG, Şenkardeş S. Eur. J. Med. Chem. 2015; 97: 786
  • 11 Maggio B, Daidone G, Raffa D, Plescia S, Mantione L, Cutuli VM. C, Mangano NG, Caruso A. Eur. J. Med. Chem. 2001; 36: 737
  • 12 Tanitame A, Oyamada Y, Ofuji K, Fujimoto M, Suzuki K, Ueda T, Terauchi H, Kawasaki M, Nagai K, Wachi M, Yamagishi J. Bioorg. Med. Chem. 2004; 12: 5515
  • 13 Aragade P, Kolhe S, Kamble H, Baheti D, Maddi V. Int. J. Drug Discovery 2012; 3: 688
  • 14 Dominquez JN, Charris JE, Caparelli M, Riggione F. Arzneimittelforschung 2002; 52: 482
  • 15 Li Y, Zhang H, Lıu J, Yang X, Liu Z. J. Agric. Food Chem. 2006; 54: 3636
  • 16 Castagnolo D, De Logu A, Radi M, Bechi B, Manetti F, Magnani M, Supino S, Meleddu R, Chisu L, Botta M. Bioorg. Med. Chem. 2008; 16: 8587
  • 17 Bandgar BP, Gawande SS, Bodade RG, Gawande NM, Khobragade CN. Bioorg. Med. Chem. 2009; 17: 8168
  • 18 Anzaldia M, Macciò C, Mazzeia M, Bertolottob M, Ottonellob L, Dallegrib F, Balbi A. Chemistry & Biodiversity 2009; 6: 1674
  • 19 Dong W, Xu J, Xıong L, Liu X, Li Z. Chin. J. Chem. 2009; 27: 579
  • 20 Faria JV, dos Santos MS, Bernardino AM. R, Becker KM, Machado GM. C, Rodrigues RF, Canto-Cavalheiro MM, Leon LL. Bioorg. Med. Chem. Lett. 2013; 23: 6310
  • 21 Kasımoğulları R, Bülbül M, Arslan BS, Gökçe B. Eur. J. Med. Chem. 2010; 45: 4769
  • 22 Cottineau B, Toto P, Marot C, Pipaud A, Chenault J. Bioorg. Med. Chem. Lett. 2002; 12: 2105
    • 23a Fustero S, Simón-Fuentes A, Sanz-Cervera JF. Org. Prep. Proced. Int. 2009; 41: 253
    • 23b Makino K, Kim HS, Kurasawa Y. J. Heterocycl. Chem. 1999; 36: 321
  • 24 Kumar SV, Yadav SK, Raghava B, Saraiah B, Ila H, Rangappa KS, Hazra A. J. Org. Chem. 2013; 78: 4960
  • 25 Ahmed MS. M, Kobayashi K, Mori A. Org. Lett. 2005; 7: 4487
  • 26 Panda N, Jena AK. J. Org. Chem. 2012; 77: 9401
  • 27 Zhang G, Ni H, Chen W, Shao J, Liu H, Chen B, Yu Y. Org. Lett. 2013; 15: 5967
  • 28 Reddy CR, Vijaykumar J, Grée R. Synthesis 2013; 45: 830
    • 29a Mahdavi M, Bialam M, Saeedi M, Jafarpour F, Foroumadi A, Shafiee A. Synlett 2015; 26: 173
    • 29b Goli-Garmroodi F, Omidi M, Saeedi M, Sarrafzadeh F, Rafinejad A, Mahdavi M, Bardajee GR, Akbarzadeh T, Firoozpour L, Shafiee A, Foroumadi A. Tetrahedron Lett. 2015; 56: 743
    • 29c Saeedi M, Mahdavi M, Foroumadi A, Shafiee A. Tetrahedron 2013; 69: 3506
    • 29d Rasouli MA, Mahdavi M, Saeedi M, Ranjbar PR, Shafiee A, Foroumadi A. J. Heterocycl. Chem. 2015; 52: 386
    • 29e Esmaeili-Marandi F, Saeedi M, Mahdavi M, Yavari I, Foroumadi A, Shafiee A. Synlett 2014; 25: 2605
    • 29f Saeedi M, Ansari S, Mahdavi M, Sabourian R, Akbarzadeh T, Foroumadi A, Shafiee A. Synth. Commun. 2015; 45: 2311
      • 2930
      • 30a Britto MM, Almeida TM. G, Leitão A, Donnici CL, Lopes MT. P, Montanari CA. Synth. Commun. 2006; 36: 3359
      • 30b Ram VJ. Indian J. Appl. Chem. 1970; 33: 394