126
Views
11
CrossRef citations to date
0
Altmetric
Original Articles

An Efficient Synthesis of Polycyclic Heterocycles Containing Pyrazolo[3,4-f]quinoline or Benzo[h]indazolo[6,7-b][1,6]naphthyridine Under Catalyst-Free Conditions

, , &
Pages 606-619 | Received 19 Mar 2014, Accepted 20 May 2014, Published online: 26 Aug 2014

REFERENCES

  • Shestopalov, A.M., Y.M. Litvinov, L.A . Rodinovskaya, O.R. Malyshev, M.N. Semenova, and V.V. Semenov. “Polyalkoxy Substituted 4H-Chromenes: Synthesis by Domino Reaction and Anticancer Activity.” ACS Combinatorial Science 14 (2012): 484–90.
  • Shestopalov, A.M., N.A. Larionova, A.E. Fedorov, L.A. Rodinovskaya, V.Y. Mortikov, A.A. Zubarev, and I.S. Bushmarinov. “Synthesis of Isomeric Isothiazolo[4′,3′:4,5]- and Isothiazolo[4′,5′:4,5]thieno[3,2-b]pyrano[2,3-d] pyridines by Combination of Domino Reactions.” ACS Combinatorial Science 15 (2013): 541–5.
  • Sun, J., Y. Sun, E.Y. Xia, and C.G. Yan. “Synthesis of Functionalized 2-Aminohydropyridines and 2-Pyridinones via Domino Reactions of Arylamines, Methyl Propiolate, Aromatic Aldehydes, and Substituted Acetonitriles.” ACS Combinatorial Science 13 (2011): 436–41.
  • Zhu, X., W. Ge, and Y. Wei. “Cerium(III)-Catalyzed One-Pot Synthesis of Quinazolinones from 2-Aminobenzamide and Aldehydes in Dimethyl Carbonate.” Polycyclic Aromatic Compounds 33 (2013): 467–72.
  • Ohemeng, K.A., B.L. Podlogar, V.N. Nguyen, J.I. Bernstein, H.M. Krause, J.J. Hilliard, and J.F. Barrett. “DNA Gyrase Inhibitory and Antimicrobial Activities of Some Diphenic Acid Monohydroxamides.” Journal of Medicinal Chemistry 40 (1997): 3292–6.
  • Sriram, D., P. Senthilkumar, M. Dinakaran, P. Yogeeswari, A. China, and V. Nagaraja. “Antimycobacterial Activities of Novel 1-(Cyclopropyl/tert-butyl/4-fluorophenyl)-1,4-dihydro- 6-nitro-4-oxo-7-(substituted secondary amino)-1,8-naphthyridine-3-carboxylic Acid.” Journal of Medicinal Chemistry 50 (2007): 6232–9.
  • Parhi, A.K., Y. Zhang, W. Saionz, K.P. Pradhan, M. Kaul, K. Trivedi, D.S. Pilch, and E.J. LaVoie. “Antibacterial Activity of Quinoxalines, Quinazolines, and 1,5-naphthyridines.” Bioorganic & Medicinal Chemistry Letters 23 (2013): 4968–74.
  • Feng, L., K. Lv, M. Liu, S. Wang, J. Zhao, X. You, S. Li, J. Cao, and H. Guo. “Synthesis and in vitro Antibacterial Activity of Gemifloxacin Derivatives Containing a Substituted Benzyloxime Moiety.” European Journal of Medicinal Chemistry 47 (2012): 55125–36.
  • Lv, K., M.L. Liu, L.S. Feng, L.Y. Sun, Y.X. Sun, Z.Q. Wei, and H.Q. Guo. “Synthesis and Antibacterial Activity of Naphthyridone Derivatives Containing Mono/Difluoro-Methyloxime Pyrrolidine Scaffolds.” European Journal of Medicinal Chemistry 47 (2012): 619–25.
  • Rudd, M.T., J. McCauley, N. Liverton, C. Grise-Bard, M.-C. Brouchu, S. Charron, V. Aulakh, B. Bachand, P. Beaulieu, H. Zaghdane, Y. Han, M. Ferrara, S. Harper, V. Summa, S. Chackalamannil, S. Venkatraman, U. Shan, and F. Velazquez. “Preparation of Macrocyclic Quinoline and Naphthyridine Peptides as HCV NS3 Protease Inhibitors Useful in the Treatment of Hepatitis C Infection.” PCT Internatinal Applications 2013, WO 2013074386 A2 20130523.
  • Zeng, L.-F., Y. Wang, R. Kazemi, S. Xu, Z.-L. Xu, T.W. Sanchez, L.-M. Yang, B. Debnath, S. Odde, H. Xie, Y.-T. Zheng, J. Ding, N. Neamati, and Y.-Q. Long. “Repositioning HIV-1 Integrase Inhibitors for Cancer Therapeutics: 1,6-Naphthyridine-7-carboxamide as a Promising Scaffold with Drug-like Properties.” Journal of Medicinal Chemistry 55 (2012): 9492–509.
  • Kobayashi, M., S. Kubo, K. Shiraki, M. Iwata, Y. Hirano, Y. Ohtsu, K. Takahashi, and Y. Shimizu. “Therapeutic Potential of ASP3258, a Selective Phosphodiesterase 4 Inhibitor, on Chronic Eosinophilic Airway Inflammation.” Pharmaceutics 90 (2012): 223–32.
  • Hoeglund, A.B., H.E. Bostic, A.L. Howard, I.W. Wanjala, M.D. Best, D.L. Baker, and A.L. Parrill. “Optimization of a Pipemidic Acid Autotaxin Inhibitor.” Journal of Medicinal Chemistry 53 (2010): 1056–66.
  • Ibrahim, S.S., A.M. Abdel-Halim, Y. Gabr, S. El-Edfawy, and R.M. Abdel-Rahman., “Synthesis and Biological Activities of Some New Fully Fused Quinazoline Derivatives.” Indian Journal of Chemistry Section B 37B (1998): 62–7.
  • Deshmukh, M.B., S. Patil, S.S. Patil, and S.D. Jadhav. “Synthesis and Antimicrobial Screening of Pyrazolo-3-Aryl Quinazolin-4(3H)ones.” Indian Journal of Pharmaceutical Sciences 72 (2010): 500–4.
  • Free, C.A. and L.E. Hall. “Antiallergic properties of SQ 13,847, an orally effective agent. II. Activity in vitro,.”Journal of Pharmacolgy and Experimental Therapuetics 213 (1980): 437–40.
  • Varano, F., D. Catarzi, V. Colotta, F.R. Calabri, O. Lenzi, G. Filacchioni, A. Galli, C. Costagli, and F. Deflorian. “Moro Stefano1-Substituted pyrazolo[1,5-c]quinazolines as Novel Gly/NMDA Receptor Antagonists: Synthesis, Biological Evaluation and Molecular Modeling Study.” Bioorganic & Medicinal Chemistry 13 (2005): 5536–49.
  • Shi, F., S. Zhang, S.-S. Wu, Y. Gao, and S.-J. Tu. “A Diversity-Oriented Synthesis of pyrazolo[4,3-f]quinoline Derivatives with Potential Bioactivities via Microwave assisted Multi-Component Reactions.” Molecular Diversity 15 (2011): 497–505.
  • Malleshwar, D., K. Gautami, and A. Jayashree. “An Efficient, High-Speed Synthesis of pyrazolo[4,3-c]quinolines. Organic Chemistry: An Indian Journal 5 (2009): 344–347.
  • Mali, J.R., U.R. Pratap, D.V. Jawale, and R.A. Mane. “Water-Mediated One-Pot Synthetic Route for pyrazolo[3,4-b]quinolines.” Tetrahedron Letters 51 (2010): 3980–2.
  • Tu, S.-J., S.-S. Wu, X.-H. Zhang, Z.-G. Han, X.-D. Cao, and W.-J. Hao. “One-Step Efficient Synthesis of pyrazolo[3,4-f]quinoline Derivatives under Microwave Irradiation.” Synthetic Communications 40 (2010): 1057–64.
  • Duggineni, S., D. Sawant, B. Saha, and B. Kundu. “Application of Modified Pictet-Spengler Reaction for the Synthesis of Thiazolo- and Pyrazolo-Quinolines.” Tetrahedron 62 (2006): 3228–41.
  • 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.
  • Chen, Z., J. Bi, and W. Su. “Synthesis and Antitumor Activity of Novel Coumarin Derivatives via a Three-component Reaction in Water.” Chinese Journal of Chemistry 31 (2013): 507–14.
  • Li, C., X.Y. Mu, Y.L. Li, Y. Liu, and X.S. Wang. “Combinatorial Synthesis of Fused Tetracyclic Heterocycles Containing [1,6]Naphthyridine Derivatives under Catalyst Free Conditions.” ACS Combinatorial Science 15 (2013): 267–72.
  • Chen, D.S., Y.J. Zhou, Y.L. Li, C.S. Yao, and X.S. Wang. “Combinatorial Synthesis of Pyrazoloquinoline and Pyrazoloacridine Derivatives with High Regioselectivity.” Combinatorial Chemistry & High Throughput Screening 16 (2013): 550–61.
  • Wang, X.S., J. Zhou, K. Yang, and Y.L. Li. “Efficient Method for the Synthesis of 2-(3-arylbenzo[f]quinolin-2-yl)ethanol Derivatives through an Unusual Ring-Opening of THF-Involved Reaction.” Tetrahedron Letters 52 (2011): 612–14.
  • Wang, X.S., M.Y. Yin, W. Wang, and S.J. Tu. “A Stereoselective Povarov Reaction Leading to exo-Tetrahydroindolo-[3,2-c]quinoline Derivatives Catalyzed by Iodine.” European Journal of Organic Chemistry (2013): 4811–8.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.