A New Protocol using Potassium Hydrogen Sulfate as the Promoter for An Efficient Synthesis of Functionalized Quinoxalines
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
- 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.
- Seitz, L.; Suling, W. J.;Reynolds, R. C."Synthesis and antimycobacterial activity of pyrazine and quinoxaline derivatives", J. Med. Chem. 2002, 45, 5604-5606.
- 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.
- 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.
- 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.
- 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.
- Jonathan, L. S.; Hiromitsu, M.; Toshihisa, M.; Vincent, M. L.; Hiroyuki, F. "Quinoxaline-bridged porphyrinoids", J. Am. Chem. Soc., 2002, 124, 13474-13479.?
- 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.
- 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.
- 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.
- 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.
- Brock,E. D.; Lewis, D. M.;Yousaf, T. I.; Harper, H. H.; WO9951688, The Procter and Gamble Company, USA, (1999).
- J.DSuderhause, S.F Martin, "Applications of Multicomponent Reactions to the Synthesis of Diverse Heterocyclic Scaffolds" Chemistry: A Eur.Journal, 2009, 15,1300-1308.
- 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.
- 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.
- Wu, Z.; Ede, N. J. "Solid-phase synthesis of quinoxalines on SynPhase? Lanterns" Tetrahedron Lett. 2001, 42, 8115-8118.
- Singh,S. K.; Gupta,P.; Duggineni, S.; Kundu B."Solid phase synthesis of quinoxalines" Synlett. 2003, 14, 2147-2150.
- 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.?
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- Paul, S.; Basu, B.? "Synthesis of libraries of quinoxalines through eco-friendly tandem oxidation?condensation or condensation reactions" Tetrahedron Lett. 2011, 52, 6597-6602.?
- 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.
- 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.
- 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.
- 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.
- 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.
- Nagarajan, R.; Perumal, P. T. "Potassium hydrogen sulfate-catalyzed reactions of indoles: a mild, expedient synthesis of bis-indolylmethanes" ChemistryLetters. 2004,33, 288-89.
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