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Original Articles

Green Synthesis of Fused Polycyclic Pyrazolo[3,4-b][1,6]naphthyridine Derivatives in Ionic Liquids via Three-Component Reaction

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Pages 478-489 | Received 24 Nov 2014, Accepted 30 Jan 2015, Published online: 14 Sep 2015

REFERENCES

  • Emmerson, A.M., and A.M. Jones. “The Quinolones: Decades of Development and Use.” Journal of Antimicrobial Chemotherapy 51 (2003): 13–20.
  • Backhouse, C.I., and J.A. Matthews. “Single-Dose Enoxacin Compared with 3-Day Treatment for Urinary Tract Infection.” Antimicrobial Agents Chemotherapy 33 (1989): 877–80.
  • Di Pietro, O., F. J. Perez-Areales, J. Juarez-Jimenez, A. Espargaro, M. V. Clos, B. Perez, R. Lavilla, R. Sabate, F. J. Luque, and D. Munoz-Torrero. “Tetrahydrobenzo[h][1,6]naphthyridine-6-chlorotacrine Hybrids as A New Family of Anti-Alzheimer Agents Targeting β-Amyloid, Tau, and Cholinesterase Pathologies.” European Journal of Medicinal Chemistry 84 (2014): 107–17.
  • Hameed, P. S., A. Raichurkar, P. Madhavapeddi, S. Menasinakai, S. Sharma, P. Kaur, R. Nandishaiah, V. Panduga, J. Reddy, V. K. Sambandamurthy, and D. Sriram. “Benzimidazoles: Novel Mycobacterial Gyrase Inhibitors from Scaffold Morphing.” Medicinal Chemistry Letters 5 (2014): 820–5.
  • Jansen, K., L. Heirbaut, R. Verkerk, J. D. Cheng, J. Joossens, P. Cos, L. Maes, A.-M. Lambeir, I. D. Meester, K. Augustyns, and P. V. der Veken. “Extended Structure-Activity Relationship and Pharmacokinetic Investigation of (4-Quinolinoyl)glycyl-2-cyanopyrrolidine Inhibitors of Fibroblast Activation Protein (FAP).” Journal of Medicinal Chemistry 57 (2014): 3053–74.
  • Zhao, X.Z., S.J. Smith, M. Metifiot, B.C. Johnson, C. Marchand, Y. Pommier, S.H. Hughes, and T.R. Burke. “Bicyclic 1-Hydroxy-2-oxo-1,2-dihydropyridine-3-carboxamide-Co-ntaining HIV-1 Integrase Inhibitors Having High Antiviral Potency against Cells Harboring Raltegravir-Resistant Integrase Mutants.” Journal of Medicinal Chemistry 57 (2014): 1573–82.
  • Dore, A., B. Asproni, A. Scampuddu, G.A. Pinna, C.T. Christoffersen, M. Langgard, and J. Kehler. “Synthesis and SAR Study of Novel Tricyclic Pyrazoles as Potent Phosphodiesterase 10A Inhibitors.” European Journal of Medicinal Chemistry 84 (2014): 181–93.
  • Ho, P.S.O. D.O. Yoon, S.Y. Han, W.I. Lee, J.S. Kim, W.S. Park, S.O. Ahn, and H.J. Kim. “Preparation of Tricyclic Fused Nitrogen-Containing Heterocyclic Compounds as Selective Histamine 4 Receptor (H4 R)Antagonists.” PCT International Applications (2013), WO 2013048214 A2 20130404.
  • Guo, C., P.R. Guzzo, M. Hadden, B.J. Sargent, L. Yet, Y.Q. Kan, O. Palyha, T.M. Kelly, X.M. Guan, and K. Rosko. “Synthesis of 7-Benzyl-5-(piperidin-1-yl)-6,7,8,9-tetrahydro-3H-pyrazolo [3,4-c][2,7]naphthyridin-1-ylamine and Its Analogs as Bombesin Receptor Subtype-3 Agonists.” Bioorganic & Medicinal Chemistry Letters 20 (2010): 2785–9.
  • Ren, P.D., B.G. Wu, G.B. Zhang, Y.P. Xie, B. Okram, V. Nikulin, X. Wang, and H.S. Choi, Preparation of Substituted Fused Naphthyridines as Protein Kinase Inhibitors, PCT International Applications WO 2007134259 A2 20071122.
  • Jayakumar, J., K.H.H.C. Parthasarathy, Y.H.H.C. Chen, T.H.C. Lee, S.C. Chuang, and C.H. Cheng, One-Pot Synthesis of Highly Substituted Polyheteroaromatic Compounds by Rhodium(III)-Catalyzed Multiple C-H Activation and Annulation, Angewandte Chemie International Edition 53 (2014): 9889–92.
  • Jha, R.R., A.K. , Danodia, and A.K. Verma “Synthesis of Fused Heterocycles via Preferential Hydroamination of o-Haloarylalkynes over N-Arylation and Successive Intramolecular C-C Bond Formation”. Tetrahedron Letters 55 (2014): 4724–30.
  • Asahrara, H., K. Muto, and N. Nishiwaki. “Safe Cyano(nitro)methylating Reagent-Michael Addition of Cyano-aci-nitroacetate Leading to δ-Functionalized α-Nitronitriles.” Tetrahedron 70 (2014): 6522–28.
  • Chen, J.H., Z.J. Xu, T. Wang, J.P. Lyssikatos, and C.O. Ndubaku. “A Versatile Annulation Route to Primary-amino-substituted Naphthyridine Esters.” Synletters (2014): 89–92.
  • Jachak, M.N., S.M. Bagul, M.A. Kazi, and B. Toche. “Novel Synthetic Protocol Toward Pyrazolo[3,4-h][1,6]naphthyridines via Friedlander Condensation of New 4-Aminopyrazolo[3,4-b]pyridine-5-carbaldehyde with Reactive α-Methylene Ketones.” Journal of Heterocyclic Chemistry 48 (2011): 295–300.
  • Beshore, D.C., R.M. Di Pardo, and S.D. Kuduk. “Preparation of 2,4,5-Trisubstituted Pyrazolo[4,3-c]quinolin-3-ones.” Tetrahedron Letters; 51 (2010): 970–3.
  • Kendre, D.B., R.B. Toche, and M.N. Jachak. “Synthesis of Novel Dipyrazolo[3,4-b:3,4-d]pyridines and Study of Their Fluorescence Behavior.” Tetrahedron 63 (2007): 11000–4.
  • Jachak, M.N., A.B. Avhale, V.J. Medhane, and R.B. Toche. “A Convenient Route for the Synthesis of Pyrazolo[3,4-d]pyrimidine, Pyrazolo[3,4-b] [1,6]naphthyridine, and Pyrazolo[3,4-b]quinoline.” Journal of Heterocyclic Chemistry 43 (2006): 1169–75.
  • Wang, X.S., Q. Li, J.R Wu, Y.L. Li, C.S. Yao, and S.J. Tu. “An Efficient and Highly Selective Method for the Synthesis of 3-Arylbenzoquinoline Derivatives Catalyzed by Iodine via Three-Component Reactions.” Synthesis (2008): 1902–10.
  • Wang, X.S., Q. Li, J.R. Wu, and S.J. Tu. “Efficient Method for the Synthesis of Pyranoquinoline, Thiopyranoquinoline, Thienoquinoline, and Naphtho[2,7]naphthyridine Derivatives Catalyzed by Iodine.” Journal of Combinatorial Chemistry; 11 (2009): 433–7.

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