Facile One-Pot Synthesis of Diversely Substituted Tetrahydroquinolines
Keywords:
Tetrahydroquinolines, Quinolyl, Antimicrobial ActivityAbstract
A facile one-pot synthesis of novel 4-quinolinyl substituted 2-alkoxy-5,6,7,8--tetrahydroquinoline-3-carbonitriles by microwave-assisted reactions of cyclohexanone and arylidene malononitriles in presence of sodium in the corresponding alcohols is described. All the newly synthesized compounds were characterized by various spectroscopic techniques and by elemental analyses. The newly synthesized compounds were evaluated for their antimicrobial activities.
References
- R. D. Larsen, E.G. Corley, A. O. King, J. D. Carrol, P. Davis, T. R. Verhoeven, P. J. Reider, M. Labelle, J. Y. Gauthier, Y. B. Xiang, R. Zamboni, J. Org. Chem. 61 (1996) 3398; (b) Y. L. Chen, K. C. Fang, J. Y. Sheu, S. L. Hsu, C. C. Tzeng, J. Med. Chem. 44 (2001) 2374;
- M. Z. Hoemann, G. Kumaravel, R. L. Xie, A. Sidhu, G. D. Cuny, J. R. Hauske, Bioorg. Med. Chem. Lett. 10 (2000) 2675.
- W. Brandt, L. Mologni, L. Preu, T. Lemcke, C. Gambacorti-Passerini, C. Kunick, Eur. J. Med. Chem. 45 (2010) 2919.
- K. S. Gudmundsson, S. D. Boggs, J. G. Catalano, A. Svolto, A. Spaltenstein, M. Thomson, P. Wheelan, S. Jenkinson, Bioorg. Med. Chem. Lett. 19 (2009) 6399.
- J. B. Crawford, G. Chen, D. Gauthier, T. Wilson, B. Carpenter, I. R. Baird, E. McEachern, A. Kaller, C. Harwig, B. Atsma, R. T. Skerlj, G. J. Bridger, Org. Process Res. Dev. 12 (2008) 823.
- A. R. Gholap, K. S. Toti, F. Shirazi, R. Kumari, M. Bhat, M. V. Deshpande, K. V. Srinivasana, Bioorg. Med. Chem. 15 (2007) 6705.
- M. M. Ghorab, F. A. Ragab, M. M. Hamed, Eur. J. Med. Chem. 44 (2009) 4211.
- J. K. Barbay, Y. Gong, M. Buntinx, J. Li, C. Claes, P. J. Hornby, G. V. Lommen, J. V. Wauweb, W. Hea, Bioorg. Med. Chem. Lett. 18 (2008) 2544.
- V. Shridharan, C. Avendano, J. C. Menendez, Synthesis (2008) 1039; (b) A. Patti, S. Pedotti, Tetrahedron 66 (2010) 5607; (c) H.-G. Cheng, C.-B. Chen, F. Tan, N.-J. Chang, J.-R. Chen, W.-J. Xiao, Eur. J. Org. Chem. 26 (2010) 4976.
- For leading references see: (a) T. Nishio, M. Tabata, H. Koyama, M. Sakamoto, Helv. Chim. Acta. 88 (2005) 78; (b) A. R. Katritzky, S. Rachwal, B. Rachwal, Tetrahedron 52 (1996) 15031; (c) G.-D. Isabelle, P. Gastaud, T. V. RajanBabu, Org. Lett. 3 (2001) 2053.
- V. Sriramurthy, O. Kwon, Org. Lett. 12 (2010) 1084; (b) T. H. Babu, G. Shanthi, P. T. Perumal, Tetrahedron Lett. 50 (2009) 2881.
- K. A. Skupinska, E. J. McEachern, R. T. Skerlj, G. J. Bridger, J Org Chem. 67 (2002) 7890.
- K.H. Chikhalia, M. J. Patel, J. Enzym Inhib. Med. Chem. 24 (2009) 960.; (b) A. B. Patel, K. H. Chikhalia, P. Kumari, Eur. J. Med. Chem. 79 (2014) 57.
Downloads
Published
Issue
Section
License
Copyright (c) IJSRSET

This work is licensed under a Creative Commons Attribution 4.0 International License.