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Microwave Assisted Gould-Jacobs Reaction for Synthesis of 3-Acetyl-4-hydroxyquinoline Derivatives
Corresponding Author(s) : Muhammad Pervaiz
Asian Journal of Chemistry,
Vol. 27 No. 8 (2015): Vol 27 Issue 8
Abstract
Different types of quinoline derivatives have been synthesized by microwave irradiation and reaction yields were compared with reported classical methodology. The emphasis on this research project was to reduce reaction times and enhance the yields of the title compounds especially by using readily available materials including aryl amines. The key intermediate formed by condensation of microwave assisted multicomponent reaction under solvent free conditions was further cyclized through a heat mediated Gould-Jacobs cyclization reaction to get substituted quinolines. A study was also made to establish one pot synthesis of quinoline derivatives in order to eliminate the purification/drying step to get key intermediate but the product yields were found to be very poor than those in the classical methodology. The synthesized compounds were characterized and identified, using different spectroscopic tools i.e., FT-IR, mass spectrometry, elemental analysis and 1H NMR.
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- P. Ball, J. Antimicrob. Chemother., 46(suppl 3), 17 (2000); doi:10.1093/oxfordjournals.jac.a020889.
- E.K. Efthimiadou, A. Karaliota and G. Psomas, Polyhedron, 27, 1729 (2008); doi:10.1016/j.poly.2008.02.006.
- M. Couturier, E.I.M. Bahassi and L. Van Melderen, Trends Microbiol., 6, 269 (1998); doi:10.1016/S0966-842X(98)01311-0.
- H. Koga, A. Itoh, S. Murayama, S. Suzue and T. Irikura, J. Med. Chem., 23, 1358 (1980); doi:10.1021/jm00186a014.
- R.B. Smith, H. Faki and R. Leslie, Synth. Commun., 41, 1492 (2011); doi:10.1080/00397911.2010.486515.
- G. Gould and W.A. Jacobs, J. Am. Chem. Soc., 61, 2890 (1939); doi:10.1021/ja01265a088.
- C.G. Dave and H.M. Joshipura, Indian J. Chem., 41B, 650 (2002).
- R.J. Kelly, Chem. Health Saf., 3, 28 (1996).
- H.L. Jackson, W.B. McCormack, C.S. Rondestvedt, K.C. Smeltz and I.E.J. Viele, Chem. Educ., 47, A175 (1970); doi:10.1021/ed047pA175.
- D.E. Clark, Chem. Health Saf., 8, 12 (2001); doi:10.1016/S1074-9098(01)00247-7.
- National Safety Council, Recognition and Handling of Peroxidizable Compounds, 1987, Data Sheet I-655-Rev. 87.
- National Research Council, Prudent Practices in the Laboratory: Handling and Disposal of Chemicals; National Academy Press: Washington, D.C., pp. 162-163 (1995).
- R.J. Kelley, Peroxidizable Organic Chemicals, Handbook of Chemical Health and Safety, American Chemical Soceity, Chap. 52, ACS (2001).
- R. Singh and Geetanjali, Synthesis, 2315 (2005); doi:10.1055/s-2005-870019.
- M. Pervaiz, M. Yousaf, A. Jabbar, A.F. Zahoor, T.H. Bokhari, A. Anjum, M. Sagir, M.A. Khan, K.G. Ali, S. Ahmad, M. Zia-ur-Rehman, S. Ashraf and K.S. Qeureshi, Asian J. Chem., 25, 2161 (2013); doi:10.14233/ajchem.2013.13374.
- M. Yousaf, M. Pervaiz, A.F. Zahoor, A.I. Hussain, M.K.H. Khosa, S. Ashraf, M. Sagir, A. Zaman and K. Shehzad, Asian J. Chem., 25, 521 (2013); doi:10.14233/ajchem.2013.13412.
References
P. Ball, J. Antimicrob. Chemother., 46(suppl 3), 17 (2000); doi:10.1093/oxfordjournals.jac.a020889.
E.K. Efthimiadou, A. Karaliota and G. Psomas, Polyhedron, 27, 1729 (2008); doi:10.1016/j.poly.2008.02.006.
M. Couturier, E.I.M. Bahassi and L. Van Melderen, Trends Microbiol., 6, 269 (1998); doi:10.1016/S0966-842X(98)01311-0.
H. Koga, A. Itoh, S. Murayama, S. Suzue and T. Irikura, J. Med. Chem., 23, 1358 (1980); doi:10.1021/jm00186a014.
R.B. Smith, H. Faki and R. Leslie, Synth. Commun., 41, 1492 (2011); doi:10.1080/00397911.2010.486515.
G. Gould and W.A. Jacobs, J. Am. Chem. Soc., 61, 2890 (1939); doi:10.1021/ja01265a088.
C.G. Dave and H.M. Joshipura, Indian J. Chem., 41B, 650 (2002).
R.J. Kelly, Chem. Health Saf., 3, 28 (1996).
H.L. Jackson, W.B. McCormack, C.S. Rondestvedt, K.C. Smeltz and I.E.J. Viele, Chem. Educ., 47, A175 (1970); doi:10.1021/ed047pA175.
D.E. Clark, Chem. Health Saf., 8, 12 (2001); doi:10.1016/S1074-9098(01)00247-7.
National Safety Council, Recognition and Handling of Peroxidizable Compounds, 1987, Data Sheet I-655-Rev. 87.
National Research Council, Prudent Practices in the Laboratory: Handling and Disposal of Chemicals; National Academy Press: Washington, D.C., pp. 162-163 (1995).
R.J. Kelley, Peroxidizable Organic Chemicals, Handbook of Chemical Health and Safety, American Chemical Soceity, Chap. 52, ACS (2001).
R. Singh and Geetanjali, Synthesis, 2315 (2005); doi:10.1055/s-2005-870019.
M. Pervaiz, M. Yousaf, A. Jabbar, A.F. Zahoor, T.H. Bokhari, A. Anjum, M. Sagir, M.A. Khan, K.G. Ali, S. Ahmad, M. Zia-ur-Rehman, S. Ashraf and K.S. Qeureshi, Asian J. Chem., 25, 2161 (2013); doi:10.14233/ajchem.2013.13374.
M. Yousaf, M. Pervaiz, A.F. Zahoor, A.I. Hussain, M.K.H. Khosa, S. Ashraf, M. Sagir, A. Zaman and K. Shehzad, Asian J. Chem., 25, 521 (2013); doi:10.14233/ajchem.2013.13412.