7th International Science Congress (ISC-2017).  International E-publication: Publish Projects, Dissertation, Theses, Books, Souvenir, Conference Proceeding with ISBN.  International E-Bulletin: Information/News regarding: Academics and Research

Synthesis of carboxamide and sulfonamide bearing novel pyrazolopyridones

Author Affiliations

  • 1Department of Industrial Chemistry, Shree M. & N. Virani Science College, Kalawad Road, Rajkot, India
  • 2Department of Chemistry, Municipal Arts & Urban Science College, Mahesana, Gujarat, India
  • 3Department of Industrial Chemistry, Shree M. & N. Virani Science College, Kalawad Road, Rajkot, India

Res.J.chem.sci., Volume 7, Issue (3), Pages 19-22, March,18 (2017)

Abstract

The reaction of pyridones with hydrazine hydrate to furnished pyrazolopyridones 1a-l followed by reaction with p-Toluenesulfonyl chloride in basic condition affords 2a-l in high yields with short reaction time. The pyridone derivatives were prepared by the reaction of ketene dithioacetals (KDTA) with cyanoacetamide usingsodium isopropoxide as an effective base. The reactions were carried out with range of solvent and found i-Propyl alcohol as suitable solvent. We have demonstrated the process of highly functionalized pyrazolopyridones in high yields.

References

  1. Schmidt A. and Dreger A. (2011)., Recent Advances in the Chemistry of Pyrazoles. Properties, Biological Activities, and Syntheses., Curr. Org. Chem., 15(9), 1423-1463.
  2. Knorr L.J. and Oettinger B. (1894)., V. Notizüber die Condensation von Hydrazinmit Dimethylacetylaceton., European Journal of Organic Chemistry, 279 (1-2), 247-248.
  3. Pechmann H.V. (1898)., PyrazolausAcetylen und Diazomethan., Berichte der deutschenchemischen Gesellschaft, 31(3), 2950-2951.
  4. Jian J.C. (2007)., Nitrogen- containing bicyclic hetroaryl compounds for the treatment of raf protein kinase-mediated diseases PCT., Int. Appl, WO 2007076092 A2 20070705
  5. Terrett N.K., Bell A.S., Brown D. and Ellis P. (1996)., 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(15), 1819-1824.
  6. Yu K., Toral B.L., Shi C., Zhang W.G., Lucas J., Shor B., Kim J., Verheijen J., Curran K., Malwitz D.J., Cole D.C., Ellingboe J., Ayral K.S., Mansour T.S., Gibbons J.J., Abraham R.T., Nowak P. and Zask A. (2009)., Biochemical, cellular, and in vivo activity of novel ATP-competitive and selective inhibitors of the mammalian target of rapamycin., Cancer Res., 69(15), 6232-6240.
  7. Stasch J.P., Becker E.M., Alonso A.C., Apeler H., Dembowsky K., Feurer A., Gerzer R., Minuth T., Perzborn E., Pleiss U., Schroder H., Schroeder W., Stahl E., Steinke W., Straub A. and Schramm M. (2001)., NO-independent regulatory site on soluble guanylatecyclase., Nature, 410(6825), 212-215.
  8. Witherington J., Bordas V., Gaiba A., Garton N.S., Naylor A., Rawlings A.D., Slingsby B.P., Smith D.G., Takle A.K. and Ward R.W. (2003)., 6-aryl-pyrazolo [3,4-b] pyridines: potent inhibitors of glycogen synthase kinase-3 (GSK-3)., Bioorg. Med. Chem. Lett., 13(18), 3055-3057.
  9. Kumar A., Ila H. and Junjappa H. (1978)., Keten dithioacetals. Part 11. Reaction of 3-cyano-4-methylthio-2(1H)-pyridones with hydrazine and guanidine: synthesis of novel substituted and fused pyrazolo [4,3-c] pyridone and pyrido[4,3-d]pyrimidine derivatives., J Chem Soc Perkin- I, 8, 857-862.
  10. Savant M.M., Gowda N.S., Pansuriya A.M., Bhuva C.V., Kapuriya N., Anandalwar S.M., Prasad S.J., Shah A. and Naliapara Y.T. (2011)., A concise synthetic strategy to functionalized chromenones via [5+1] heteroannulation and facile C–N/C–S/C–O bond formation with various nucleophiles., Tetrahedron Letters, 52(2), 254-257.
  11. Savant M.M., Pansuriya A.M., Bhuva C.V., Kapuriya N., Patel A.S., Audichya V.B., Pipaliya P.V. and Naliapara Y.T. (2009)., Water Mediated Construction of Trisubstituted Pyrazoles/Isoxazoles Library Using Ketene Dithioacetals., Journal of Combinatorial Chemistry, 12(1), 176-180.
  12. Davies N.G.M., Browne H., Davis B., Drysdale M.J., Foloppe N., Geoffrey S., Gibbons B., Hart T., Hubbard R., Jensen M.R., Mansell H., Massey A., Matassova N., Moore J.D., Murray J., Pratt R., Ray S., Robertson A., Roughley S.D., Schoepfer J., Scriven K., Simmonite H., Stokes S., Surgenor A., Webb P., Wood M., Wright L. and Brough P. (2012)., Targeting conserved water molecules: Design of 4-aryl-5-cyanopyrrolo [2,3-d] pyrimidine Hsp90 inhibitors using fragment-based screening and structure-based optimization., Bioorganic & Medicinal Chemistry, 20(22), 6770-6789.
  13. Moffett K., Konteatis Z., Nguyen D., Shetty R., Ludington J., Fujimoto T., Lee K.L., Chai X., Namboodiri H., Karpusas M., Dorsey B., Guarnieri F., Bukhtiyarova M., Springman E. and Michelotti E. (2011)., Discovery of a novel class of non-ATP site DFG-out state p38 inhibitorsutilizing computationally assisted virtual fragment-based drug design (vFBDD)., Bioorganic & Medicinal Chemistry Letters, 21(23), 7155-7165.