A New Protocol using Potassium Hydrogen Sulfate as the Promoter for An Efficient Synthesis of Functionalized Quinoxalines

Authors

  • Iqbal N. Shaikh  Department of Chemistry, Post Graduate & Research Centre, AKI’s Poona College of Arts, Science & Commerce, Pune, Maharashtra, India
  • Faazil Shaikh  Department of Chemistry, Yashwant Mahavidyalaya, Nanded, Maharashtra,India
  • Baseer M. Abdul  Department of Chemistry, Yashwant Mahavidyalaya, Nanded, Maharashtra,India

Keywords:

Green chemistry, KHSO4, medicinally important.

Abstract

A simple, greener and highly efficient method for the synthesis of biologically important functionalized quinoxalines has been developed employing KHSO4as a promoter in water. To the best of our knowledge this transformation is achieved for the first time using an organic catalyst. A small library of quinoxaline conjugates have been synthesized using this green chemistry oriented effective protocol.

References

  1. Lindsley, C. W.;? Zhao, Z.; Leister, W. H.; Robinson,R. G.;Barnett, S. F., Defeo Jones D.;Jones, R. E.; Hartman,G. D.; Huff, J. R.; Huber,H. E.; Duggan, M. E."Allosteric Akt (PKB) inhibitors: discovery and SAR of isozyme selective inhibitors"Bioorg. Med. Chem. Lett., 2005, 15, 761-764.
  2. Seitz, L.; Suling, W. J.;Reynolds, R. C."Synthesis and antimycobacterial activity of pyrazine and quinoxaline derivatives", J. Med. Chem. 2002, 45, 5604-5606.
  3. Loriga, M.; Piras, S.; Sanna, P.; Paglietti, G. "Quinoxaline chemistry. Part 7. 2-[aminobenzoates]-and 2-[aminobenzoylglutamate]-quinoxalines as classical antifolate agents" Synthesis and evaluation of in vitro, Farmaco, 1997, 52, 157-166.
  4. Abdelfattah, M. S.; Kazufumi, T.; Ishibashi, M. "Izumiphenazines A? C: Isolation and Structure Elucidation of Phenazine Derivatives from Streptomyces sp. IFM 11204",J. Nat.Prod., 2010,? 73, 1999-2002.
  5. Rajule, R.;? Bryant, V. C.; Lopez, H.;Luo, X.; Natarajan, A."Perturbing pro-survival proteins using quinoxaline derivatives: A structure?activity relationship study", Bioorg. Med. Chem., 2012,20, 2227-2234.
  6. Watanabe, K.; Hotta, K.; Praseuth, A. P.; Koketsu, K.; Migita, A.; Boddy, C. N.; Wang, C. C.; Oguri, H.; Oikawa, H."Total biosynthesis of antitumor nonribosomal peptides in Escherichia coli", Nat. Chem.Biol., 2006,8, 423-428.
  7. Jonathan, L. S.; Hiromitsu, M.; Toshihisa, M.; Vincent, M. L.; Hiroyuki, F. "Quinoxaline-bridged porphyrinoids", J. Am. Chem. Soc., 2002, 124, 13474-13479.?
  8. Thomas, J. K. R.;Marappan, V.;Jiann, T. L.; Chang,? H. C.; Yu-ai, T. "Chromophore-labeled quinoxaline derivatives as efficient electroluminescent materials"Chem. Mater.2005, 17, 1860-1866.
  9. Obrien, D.; Weaver, M. S.; Lidzey, D. G.; Bradley,? D. C. "Use of poly (phenyl quinoxaline) as an electron transport material in polymer light?emitting diodes" Appl. Phys. Lett., 1996, 69, 881.
  10. Dailey, S.; Feast, J. W.; Peace, R. J.; Saga, R. C.; Till, S.;Wood, E. L. "Synthesis and device characterisation of side-chain polymer electron transport materials for organic semiconductor applications" J. Mater. Chem.2001,11, 2238-2243.
  11. Kadir, D.;? Mustafa, C.;? Cihan, O.;? Mesude, Z. Y.; Burak, G.;? Serafettin, d.;? Ceylan,? Z. "Synthesis and photovoltaic characterization of triarylamine-substituted quinoxaline push?pull dyes to improve the performance of dye-sensitized solar cells" Turk. J. Chem. 2017, 41, 309-322.
  12. Brock,E. D.; Lewis, D. M.;Yousaf, T. I.; Harper, H. H.; WO9951688, The Procter and Gamble Company, USA, (1999).
  13. J.DSuderhause, S.F Martin, "Applications of Multicomponent Reactions to the Synthesis of Diverse Heterocyclic Scaffolds" Chemistry: A Eur.Journal, 2009, 15,1300-1308.
  14. Attanasi, O. A.; DeCrescentiniL.;Filippone, P.;Mantellini, F.; Santeusanio, S. "A New Convenient Liquid?and Solid?Phase Synthesis of Quinoxalines from (E)?3?Diazenylbut?2?enes" Helv. Chim. Acta. 2001, 84, 2379-2386.
  15. Attanasi, O. A.; De Crescentini, L.;Filippone, P.;Mantellini, F.;Santeusanio, S. "Improved synthesis of substituted quinoxalines from new N=N-polymer-bound 1, 2-diaza-1, 3-butadienes" Synlett,2003, 8, 1183-1185.
  16. Wu, Z.; Ede, N. J. "Solid-phase synthesis of quinoxalines on SynPhase? Lanterns" Tetrahedron Lett. 2001, 42, 8115-8118.
  17. Singh,S. K.; Gupta,P.; Duggineni, S.; Kundu B."Solid phase synthesis of quinoxalines" Synlett. 2003, 14, 2147-2150.
  18. More, S. V.; Sastry, M. N. V.;Wang, C. C.; Yao, C. F. "Molecular iodine: a powerful catalyst for the easy and efficient synthesis of quinoxalines" Tetrahedron Lett. 2005, 46, 6345-6348.?
  19. More, S. V.; Sastry, M. N. V.;? Yao, C. F. "Cerium (IV) ammonium nitrate (CAN) as a catalyst in tap water: A simple, proficient and green approach for the synthesis of quinoxalines" Green Chem.2006, 8, 91-95.
  20. Bhosale, R. S.;? Sarda, S. R.; Andhapure, S. S.; Jadhav, W. N.; Bhusare, S. R.; Pawar, R. P. "An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using molecular iodine as the catalyst" Tetrahedron Lett. 2005, 46, 7183-7186.
  21. Bahman, T.; Alireza, S.;? Elaheh, A. "Synthesis and application of polyvinylimidazole-based Bronsted acidic ionic liquid grafted silica as an efficient heterogeneous catalyst in the preparation of " Turk. J. Chem. 2016, 40, 422-433.
  22. Raw, S. A.; Wilfred, C. D.; Taylor, R. J. K.T. "Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds" Org. Biomol. Chem.2004, 2, 788-796.
  23. Kim, S. Y.; Park, K. H.; Chung, Y. K. "Manganese (IV) dioxide-catalyzed synthesis of quinoxalines under microwave irradiation" Chem. Commun. 2005, 10, 1321-1323.
  24. Meshram, H. M.; Kumar, G. S.; Ramesh, P.; Reddy, B. C. "A mild and convenient synthesis of quinoxalines via cyclization?oxidation process using DABCO as catalyst"Tetrahedron Lett. 2010, 51, 2580-2585.
  25. Bhattacharya, T. "Self-assembled monolayer coated gold-nanoparticle catalyzed aerobic oxidation of ?-hydroxy ketones in water: an efficient one-pot synthesis of quinoxaline" Catal. Sci. Technol. 2012, 2, 2216-2220.
  26. Sithambaram, S.; Ding Y.; Li, W.;Shen, X.;Gaenzler, F.;Suib, S. L."Manganese octahedral molecular sieves catalyzed tandem process for synthesis of quinoxalines" Green Chem.2008, 10,1029-1032.
  27. Akkilagunta,V. K.; Reddy, V. P.; Kakulapati, R. R. "Aqueous-phase aerobic oxidation of alcohols by ru/c in the presence of cyclodextrin: one-pot biomimetic approach to quinoxaline synthesis" Synlett2010, 17, 2571-2574.
  28. Paul, S.; Basu, B.? "Synthesis of libraries of quinoxalines through eco-friendly tandem oxidation?condensation or condensation reactions" Tetrahedron Lett. 2011, 52, 6597-6602.?
  29. Wang, X. S, Zhaou, J, Yang K, Yao, C.S. "Yb(OTf)3: an efficient catalyst for the synthesis of 3-arylbenzo [f]quinoline-1,2-dicarboxylate derivatives via imino-Diels?Alder reaction" 2010, 51, 5721.
  30. Kotharkar, S. A.;Shinde, D. B."Mercuric iodide (HgI 2) as an oxidizing agent for the synthesis of quinoxaline" Bull. Korean Chem. Soc.2006, 27, 1466-1468.
  31. Raw, S. A.; Wilfred C. D.; Taylor, R. J. K. "Preparation of quinoxalines, dihydropyrazines, pyrazines and piperazines using tandem oxidation processes" Chem. Commun.2003, 2286-2287.
  32. Kamal, A.; Faazil, S.;Janaki, M. R.; Ashraf, Md.;Balakrishna, M.; Pushpavalli, S.N.C.V.L.; Nibedita, P.; Pal-Bhadra, M. "Synthesis and study of benzothiazole conjugates in the control of cell proliferation by modulating Ras/MEK/ERK-dependent pathway in MCF-7 cells" Bioorg. Med ChemLett.2013, 23, 5733?5739.
  33. Nazeruddin,G. M.; Suryawanshi,S. B.;? Iqbal,N. Shaikh. "Ultra Sound Assisted Oxidation of Alcohols by Fe (NO3)(3) as an oxidant in presence of Phase Transfer Catalyst"? Res. J. Chem. Env.2010, 14, 57-59.
  34. Nagarajan, R.; Perumal, P. T. "Potassium hydrogen sulfate-catalyzed reactions of indoles: a mild, expedient synthesis of bis-indolylmethanes" ChemistryLetters. 2004,33, 288-89.

Downloads

Published

2017-12-15

Issue

Section

Research Articles

How to Cite

[1]
Iqbal N. Shaikh, Faazil Shaikh, Baseer M. Abdul "A New Protocol using Potassium Hydrogen Sulfate as the Promoter for An Efficient Synthesis of Functionalized Quinoxalines" International Journal of Scientific Research in Science and Technology(IJSRST), Online ISSN : 2395-602X, Print ISSN : 2395-6011,Volume 3, Issue 9, pp.264-268, November-December-2017.