9th International Science Congress (ISC-2019).  International E-publication: Publish Projects, Dissertation, Theses, Books, Souvenir, Conference Proceeding with ISBN.  International E-Bulletin: Information/News regarding: Academics and Research

Simple Grinding, Catalyst-free, One-Pot, Three-Component Synthesis of Polysubstituted Amino Pyrazole

Author Affiliations

  • 1Department of Chemistry, Arts, Science and Commerce College, Naldurg, Tq-Tuljapur, Dist.- Osmanabad- 413602, MS, INDIA

Res.J.chem.sci., Volume 4, Issue (9), Pages 16-21, September,18 (2014)

Abstract

An efficient, one-pot, three-component catalyst free synthesis of various biologically important heterocyclic compounds is described by simple grinding of aromatic aldehydes, malononitrile, and phenyl hydrazine.

References

  1. Hasaninejad A., Zare A. and Shekouhy M., Sulfuric acid modified PEG-6000 (PEG-OSO3H): an efficient, bio-degradable and reusable polymeric catalyst for the solvent-free synthesis of poly-substituted quinolines under microwave irradiation, Green Chem, 13, 958–964 (2011)
  2. Hasaninejad A., Zare A. and Shekouhy M., Catalyst-free one-pot four component synthesis of polysubstituted imidazoles in neutral. Ionic liquid 1-butyl-3-methylimidazolium bromide, J Comb Chem,12, 844–849 (2010)
  3. Anzai K., Furuse M., Yoshid a A., Matsuyama A., Moritake T., Tsuboi K. and Ikota N., In vivo radioprotection of mice by 3-methyl-1- phenyl-2-pyrazolin-5-one (Edaravone; Radicut), a clinical drug, J Radiat Res.,45, 319–323 (2004)
  4. Daidone G., Maggio B., Plescia S., Raffa D., Musiu C., Milia C., Perra G. and Marongiu M.E., Antimicrobial and antineoplastic activities of new 4-diazopyrazole derivatives, EurJ Med Chem.,33, 375–382 (1998)
  5. Tanitame A., Oyamada Y. and Ofuji K. Design, synthesis and structure-activity relationship studies of novel indazole analogues as DNA gyrase inhibitors with Gram-positive antibacterial activity, Bioorg Med Chem Lett14, 2857–2862 (2004)
  6. Nauduri D. and Reddy G.B. Antibacterials and antimycotics: part 1: synthesis and activity of 2-pyrazoline derivatives, Chem Pharm Bull.,46, 1254–1260 (1998)
  7. Hiyama Y., Suzuki K.M. and Yamagishi J., Synthesis and antibacterial activity of a novel series of potent DNA gyrase inhibitors, Pyrazole derivatives, J Med Chem.,47, 3693–3696 (2004)
  8. Tewari A.K. and Mishra A., Synthesis and anti-inflammatory activities of N4N5-disubstituted-3-methyl-1H-pyrazolo[3,4- c]pyridazines, Bioorg Med Chem, 9, 715–718 (2001)
  9. Gursoy S.A., Demirayak G. and Capan K., Synthesis and preliminary evaluation of new 5-pyrazolinone derivatives as analgesic agents, Eur J Med Chem., 35, 359–364 (2000)
  10. Bailey D.M., Hansen P.E., Hlavac A.G., Baizman E.R., Pearl J., Defelice A.F., Feigenson M.E., 3,4-Diphenyl-1H-pyrazole-1- propanamine antidepressants, J Med Chem,28, 256–260 (1985)
  11. Katiyar S.B., Srivastava K., Purib S.K. and Chauhana PMS, Synthesis of 2-[3,5-substituted pyrazol-1-yl]-4,6-trisubstituted triazine derivatives as antimalarial agents, Bioorg Med Chem Lett.,15, 4957–4960 (2005)
  12. Farag A.M., Ali K.A., Mayhoub A.S., Abdalla T.M., Amr A.E., Abdel- Hafez N. and Abdalla M.M., Design, synthesis and structureactivity relationship study of novel pyrazole-based heterocycles as potential antitumor agents, Eur J Med Chem,45, 5887–5898 (2010)
  13. Allen S.H., Johns B.A., Gudmundsson K.S. and Freeman G.A., Synthesis of C-6 substituted pyrazolo[1,5-]pyridines with potent activity against herpesviruses, Bioorg Med Chem.,14, 944–954 (2006)
  14. He F.Q., Liu X.H., Wang B.L. and Li Z.M., Synthesis and biological activities of novel bis-heterocyclic pyrrodiazole derivatives, Heteroatom Chemistry,19, 21–27 (2008)
  15. Parlow J.J., Synthesis of pyrazolecarbonylaminopyridine carboxamides as herbicides, J. Heterocycl Chem 35, 1493–1499 (1998)
  16. Kumar V., Aggarwal R., Tyagi P. and Singh S.P., Synthesis and antibacterial activity of some new 1-heteroaryl-5-amino-4-phenyl- 3-trifluoromethylpyrazoles, Eur J Med Chem.,40, 922–927 (2005)
  17. Penning T.D., Talley J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Doctor S., Graneto M.J., Lee L.F., Malecha J.W., Miyashiro J.M., Rogers R.S., Rogier D.J., Yu S.S., Anderson G.D., Burton E.G., Cogburn J.N., Gregory S.A., Koboldt C.M., Perkins W.E., Seibert K., Veenhuizen A.W., Zhang Y.Y., Isakson P.C., Synthesis and biological evaluation of the 1, 5-diarylpyrazole class of cyclooxygenase-2 inhibitors:? identification of 4-[5-(4-methylphenyl)-3- (trifluoromethyl)-1pyrazol- 1-yl]benzenesulfonamide (SC-58635, celecoxib), J Med Chem, 40, 1347–1365 (1997)
  18. Terrett NK, Bell AS, Brown D, Ellis P Sildenafil (VIAGRATM), a potent and selective inhibitor of type 5 cGMP phosphodiesterase with utility for the treatment of male erectile dysfunction, Bioorg Med Chem Lett., 6, 1819–1824 (1996)
  19. Varvounis G, Fiamegos Y, Pilidis G Pyrazol-3-ones. Part II: reactions of the ring atoms, Adv Heterocycl Chem., 87, 141–272(2004)
  20. Salaheldin A.M., Oliveira-Campos A.M.F., Rodrigues L.M., N-Bromosuccinimide assisted oxidation of 5-aminopyrazoles: formation of bis diazenylderivatives, Tetrahedron Lett48, 8819–8822 (2007)
  21. Varvounis G., Fiamegos Y., PilidisGPyrazol-3-ones, Part III: reactivity of the ring substituents, Adv Heterocycl, Chem., 95, 27–141(2007)
  22. Martin R., Rivero M.R., Buchwald S.L., Domino Cu-catalyzed C–Ncoupling/hydroamidation: a highly efficient synthesis of nitrogen heterocycles, AngewChem Int Ed Engl,45, 7079–7082 (2006)
  23. Hasaninejad A., Shekouhy M., Golzar N., Zare A. and Doroodmand M.M., Silica bonded n -propyl-4-aza-1- azoniabicyclo[2.2.2]octane chloride (SB-DABCO): a highly efficient, reusable and new heterogeneous catalyst for the synthesis of 4 H -benzo[b] pyran derivatives, Appl Catal A: General,402, 11–22 (2011)