Multistep organic synthesis leading to the formation of triazinothiazoloquinoxalines involving cost effective rea-gents

  • Authors

    • Amar Yadav lucknow university, india
    • Vinod Pandey lucknow university,india
    2017-09-05
    https://doi.org/10.14419/ijsw.v5i2.6154
  • , B-Lactamase, Brevity, 2, 3-Dichloroquinoxaline.
  • Abstract

    A simple and efficient chemical method has been attempted for the synthesis of biologically and commercially important 2-aryl [-s-] triazino [1], [3], [5] thiazolo [6], [5-b] quinoxalin -4- thiones in moderate to excellent yields through cyclization reaction of o-phenylenediamino using readily available and fewer costly reagents viz. oxalic acid, PCl5thiourea, aromatic aldehydes and ammonium thiocyanate at an ambient temperature.

  • References

    1. [1] Buynak, J.D; Borate, H.B.; Lamb, G.W.;Khasnis, D.D.; Husting, C., Isom, H.; Siriwardane, U. J. Org Chem 1993, 58, 1325-1335.https://doi.org/10.1021/jo00058a008.

      [2] (a) Bush, K. Antimicrob. Agents Chemother 1989, 33, 264. (b) Bush, K. Antimicrob. Agents Chemother 1989, 33, 271.https://doi.org/10.1128/AAC.33.3.264.

      [3] (a) Knowles, J.R. AccChem Res 1985, 18, 97. (b) Knowles, J.R. AccChem Res 1983, 6, 90.https://doi.org/10.1021/ar00112a001.

      [4] Wagle, S; Adhikari, A.V.; Kumari, N.S. Ind J Chem2008, 47B, 439.

      [5] Khan, S.A.; Salim, K.; Khan, Z. European J Med Chem 2007, 42, 103.https://doi.org/10.1016/j.ejmech.2006.07.006.

      [6] Coulthord, C.E.; Hale, L.J.; Gurd, M.R. Brit J Pharmacol 1954, 10, 394.

      [7] Francis, J.; Landquist, J.K.; Levi, A.A.; Silk, J. A.; Thorp, J.M. Biochem J, 1956, 63, 455.https://doi.org/10.1042/bj0630455.

      [8] Hennessey, T.D.; Edwards, J.R. Vet Rec 1972, 90, 187.https://doi.org/10.1136/vr.90.7.187.

      [9] Kotharkar, S.A.; Shinde, D.B. Biorg Med ChemLett 2006, 16, 6181.https://doi.org/10.1016/j.bmcl.2006.09.040.

      [10] Waring, M.J.; Ben Hadda, T.; Kotchevar, A.T.; Ramdani, A.; Touzani, R.; Elkadiri, S.; Hakkou, A.; Bouakka, M.; Ellias, T. Molecules, 2002, 7, 641.https://doi.org/10.3390/70800641.

      [11] Grande, F.; Aiello, F.; Grazia, O.D.; Brizzi, A.; Garofaloa, A.; Neamati, N.Biorg.Medchem 2007, 15, 288.https://doi.org/10.1016/j.bmc.2006.09.073.

      [12] Lee, I.S.; Waring, M.J. Biochem J 1978, 173, 129.https://doi.org/10.1042/bj1730129.

      [13] Waring, M.J.; Wakelin, L.P.G. Nature 1974, 252, 653.https://doi.org/10.1038/252653a0.

      [14] Lee, J.S.; Waring, M.J. Biochem J 1978, 173, 115.https://doi.org/10.1042/bj1730115.

      [15] Klcim, J.; Bender, R.; Billhardt, U.; Meichsner, C.; Riess, G.; Rosner, M.; Winkler, I.; Paessens, A. Antimicrobial agents and chemotherapy, 1993, 1659.

      [16] Yolanda, S.; Elena, M.; Javier, F.; Angel, M.; Gerain, L.D. Arzneimittel-Forschung 1999, 49(1), 55.

      [17] Williamson, H.E.; Shiderman, F.E.; Lescher, D.A. J Pharmacol Exp. Ther 1959, 126, 82.

      [18] Glandyil, J.M.Z.; Hunt, Z.H.; Jack, D.; Haff, R,F.; Boyle, J.J.; Steward, R.C.; Ferlanto, R.J. Nature, 1968, 221, 286.

      [19] Boyle, J.J.; Ravpp, W.G.; Stanfield, F.J.; Haff, R.F.; Diek, E.C.; D' Allesio, D; Dick, C.R. Ann N Y AcadSci 1970, 173, 477.https://doi.org/10.1111/j.1749-6632.1970.tb53436.x.

      [20] Gwaltney, T.M. ProcSocExpBiol Med 1970, 133, 1148https://doi.org/10.3181/00379727-133-34642.

      [21] Haff, R.F.; Flagg, W.B.; Gallo, J.J.; Hoover, J.R.E.; Miller, J.A.; Pinto, C.A.; Pegano, J.F. OrocSocExpBiol 1972, 141, 475.

      [22] Sorm, F.; Vesely, J. Neoplasm, 1964, 11, 123.

      [23] Jurovcik, M.; Raska, K.; Sormova, J.; Sorm, P. Collect Czech chem common 1965, 20, 3370.

      [24] Mohan, J; Kumar, A. Ind J Het Chem 2003, 12, 283-284.

      [25] Mohan. J. IndJHetchem 1998, 32, 953.

      [26] Upadhyay, M. in "Synthesis of some fused ring heterocyclic Compounds for studying their biological activity" A Ph.D thesis, Chemistry Department, Lucknow University, Lucknow.P.159 (2005).

  • Downloads

  • How to Cite

    Yadav, A., & Pandey, V. (2017). Multistep organic synthesis leading to the formation of triazinothiazoloquinoxalines involving cost effective rea-gents. International Journal of Scientific World, 5(2), 131-134. https://doi.org/10.14419/ijsw.v5i2.6154

    Received date: 2016-04-23

    Accepted date: 2016-05-18

    Published date: 2017-09-05