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Synthesis and Antibacterial Assay of 9-Substituted Aryl-1,8-dioxo-octahydroxanthenes
Corresponding Author(s) : Yellajyosula Lakshmi Narasimha Murthy
Asian Journal of Chemistry,
Vol. 26 No. 15 (2014): Vol 26 Issue 15
Abstract
The present report highlights the heterogeneous catalytic activity of nano copper ferrite for the one pot synthesis of 9-substituted aryl-1,8-dioxo-octahydroxanthenes when dimedone reacts with various aromatic aldehydes under solvent free conditions, catalyzed by nano catalyst. The main advantageous of this protocol includes excellent yields, mild reaction conditions and short reaction times.
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- T. Hideo, Jpn. Tokkyo Koho JP 56,005,480 (1981); Chem. Abstr., 95, 80922b (1981).
- R.W. Lambert, J.A. Martin, J.H. Merrett, K.E.B. Parkes and G.J. Thomas, Chem. Abstr., 126, 212377y (1997).
- G. Saint-Ruf, Huynh-Trong-Hieu and J.-P. Poupelin, Naturwissenschaften, 62, 584 (1975); doi:10.1007/BF01166986.
- R.M. Ion, Prog. Catal., 2, 55 (1997).
- R.M. Ion, D. Frackowiak, A. Planner and K. Wiktorowicz, Acta Biochim. Pol., 45, 833 (1998).
- C.G. Knight and T. Stephens, Biochemistry, 258, 683 (1989).
- S. Hatakeyama, N. Ochi, H. Numata and S. Takano, J. Chem. Soc. Chem. Commun., 1202 (1988); doi:10.1039/c39880001202.
- G.M. Cingolani, F. Gualtieri and M. Pigini, J. Med. Chem., 12, 531 (1969); doi:10.1021/jm00303a616.
- S. Ahadi, H.R. Khavasi and A. Bazgir, Chem. Pharm. Bull. (Tokyo), 56, 1328 (2008); doi:10.1248/cpb.56.1328.
- C.N. O'Callaghan and T.B.H. McMurry, J. Chem. Res. (S), 78 (1997); doi:10.1039/A607362J.
- E.C. Horning and M.G. Horning, J. Org. Chem., 11, 95 (1946); doi:10.1021/jo01171a014.
- X.S. Wang, D.Q. Shi, Y.L. Li, H. Chen, X.Y. Wei and Z.M. Zong, Arkivoc, 117 (2005).
- T.S. Jin, J.S. Zhang, J.C. Xiao, A.Q. Wang and T.S. Li, Synlett, 866 (2004); doi:10.1055/s-2004-820022.
- F. Darviche, S. Balalaei, F. Chadegani and P. Salehi, Synth. Commun., 37, 1059 (2007); doi:10.1080/00397910701196520.
- T.-S. Jin, J.-S. Zhang, A.-Q. Wang and T.-S. Li, Ultrason. Sonochem., 220 (2006); doi:10.1016/j.ultsonch.2005.04.002.
- M. Dabiri, M. Baghbanzadeh and E. Arzroomchilar, Catal. Commun., 9, 939 (2008); doi:10.1016/j.catcom.2007.09.023.
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- B. Das, P. Thirupathi, K.R. Reddy, B. Ravikanth and L. Nagarapu, Catal. Commun., 8, 535 (2007); doi:10.1016/j.catcom.2006.02.023.
- P. Srihari, S.S. Mandal, J.S.S. Reddy, R.S. Rao and J.S. Yadav, Chin. Chem. Lett., 19, 771 (2008); doi:10.1016/j.cclet.2008.05.005.
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- G.H. Mahdavinia, M.A. Bigdeli and Y.S. Hayeniaz, Chin. Chem. Lett., 20, 539 (2009); doi:10.1016/j.cclet.2008.12.026.
- G.I. Shakibaei, P. Mirzaei and A. Bazgir, Appl. Catal. A, 325, 188 (2007); doi:10.1016/j.apcata.2007.03.008.
- S. Kantevari, R. Bantu and L. Nagarapu, J. Mol. Catal. Chem., 269, 53 (2007); doi:10.1016/j.molcata.2006.12.039.
- M.T. Maghsoodlou, S.M. Habibi-Khorassani, Z. Shahkarami, N. Maleki and M. Rostamizadeh, Chin. Chem. Lett., 21, 686 (2010); doi:10.1016/j.cclet.2010.02.005.
- G. Karthikeyan and A. Pandurangan, J. Mol. Catal. Chem., 311, 36 (2009); doi:10.1016/j.molcata.2009.06.020.
- Y.L.N. Murthy, B.S. Diwakar, B. Govindh, K. Nagalakshmi, I.V. Kasi Viswanath and R. Singh, J. Chem. Sci., 124, 639 (2012); doi:10.1007/s12039-012-0258-9.
- C. Perez, M. Pauli and P. Bazevque, Acta Biologiae et Medicine Experimentalis, 15, 113 (1990).
- M.A. Pfaller, M. Castanheira, D.J. Diekema, S.A. Messer, G.J. Moet and R.N. Jones, J. Clin. Microbiol., 48, 1592 (2010); doi:10.1128/JCM.02445-09.
- Clinical Laboratory Standards Institute Methods for Dilution Antimicrobial Susceptibility Test for Bacteria That Grow Aerobically; Approved Standard M 07-A9, edn 9, vol. 32, No. 2, p. 12 (2012).
- J.-M. Yang, J. Comput. Chem., 25, 843 (2004); doi:10.1002/jcc.20013.
- J.M. Yang and C.C. Chen, Proteins, 55, 288 (2004); doi:10.1002/prot.20035.
- A. Bekaert, J. Andrieux and M. Plat, Tetrahedron Lett., 33, 2805 (1992); doi:10.1016/S0040-4039(00)78863-0.
- K. Venkatesan, S.S. Pujari, R.J. Lahoti and K.V.C. Srinivasan, Ultrason. Sonochem., 15, 548 (2008); doi:10.1016/j.ultsonch.2007.06.001.
References
T. Hideo, Jpn. Tokkyo Koho JP 56,005,480 (1981); Chem. Abstr., 95, 80922b (1981).
R.W. Lambert, J.A. Martin, J.H. Merrett, K.E.B. Parkes and G.J. Thomas, Chem. Abstr., 126, 212377y (1997).
G. Saint-Ruf, Huynh-Trong-Hieu and J.-P. Poupelin, Naturwissenschaften, 62, 584 (1975); doi:10.1007/BF01166986.
R.M. Ion, Prog. Catal., 2, 55 (1997).
R.M. Ion, D. Frackowiak, A. Planner and K. Wiktorowicz, Acta Biochim. Pol., 45, 833 (1998).
C.G. Knight and T. Stephens, Biochemistry, 258, 683 (1989).
S. Hatakeyama, N. Ochi, H. Numata and S. Takano, J. Chem. Soc. Chem. Commun., 1202 (1988); doi:10.1039/c39880001202.
G.M. Cingolani, F. Gualtieri and M. Pigini, J. Med. Chem., 12, 531 (1969); doi:10.1021/jm00303a616.
S. Ahadi, H.R. Khavasi and A. Bazgir, Chem. Pharm. Bull. (Tokyo), 56, 1328 (2008); doi:10.1248/cpb.56.1328.
C.N. O'Callaghan and T.B.H. McMurry, J. Chem. Res. (S), 78 (1997); doi:10.1039/A607362J.
E.C. Horning and M.G. Horning, J. Org. Chem., 11, 95 (1946); doi:10.1021/jo01171a014.
X.S. Wang, D.Q. Shi, Y.L. Li, H. Chen, X.Y. Wei and Z.M. Zong, Arkivoc, 117 (2005).
T.S. Jin, J.S. Zhang, J.C. Xiao, A.Q. Wang and T.S. Li, Synlett, 866 (2004); doi:10.1055/s-2004-820022.
F. Darviche, S. Balalaei, F. Chadegani and P. Salehi, Synth. Commun., 37, 1059 (2007); doi:10.1080/00397910701196520.
T.-S. Jin, J.-S. Zhang, A.-Q. Wang and T.-S. Li, Ultrason. Sonochem., 220 (2006); doi:10.1016/j.ultsonch.2005.04.002.
M. Dabiri, M. Baghbanzadeh and E. Arzroomchilar, Catal. Commun., 9, 939 (2008); doi:10.1016/j.catcom.2007.09.023.
B. Das, P. Thirupathi, I. Mahender, V.S. Reddy and Y.K. Rao, J. Mol. Catal. Chem., 247, 233 (2006); doi:10.1016/j.molcata.2005.11.048.
B. Das, P. Thirupathi, K.R. Reddy, B. Ravikanth and L. Nagarapu, Catal. Commun., 8, 535 (2007); doi:10.1016/j.catcom.2006.02.023.
P. Srihari, S.S. Mandal, J.S.S. Reddy, R.S. Rao and J.S. Yadav, Chin. Chem. Lett., 19, 771 (2008); doi:10.1016/j.cclet.2008.05.005.
S. Rostamizadeh, A.M. Amani, G.H. Mahdavinia, G. Amiri and H. Sepehrian, Ultrason. Sonochem., 17, 306 (2010); doi:10.1016/j.ultsonch.2009.10.004.
G.H. Mahdavinia, M.A. Bigdeli and Y.S. Hayeniaz, Chin. Chem. Lett., 20, 539 (2009); doi:10.1016/j.cclet.2008.12.026.
G.I. Shakibaei, P. Mirzaei and A. Bazgir, Appl. Catal. A, 325, 188 (2007); doi:10.1016/j.apcata.2007.03.008.
S. Kantevari, R. Bantu and L. Nagarapu, J. Mol. Catal. Chem., 269, 53 (2007); doi:10.1016/j.molcata.2006.12.039.
M.T. Maghsoodlou, S.M. Habibi-Khorassani, Z. Shahkarami, N. Maleki and M. Rostamizadeh, Chin. Chem. Lett., 21, 686 (2010); doi:10.1016/j.cclet.2010.02.005.
G. Karthikeyan and A. Pandurangan, J. Mol. Catal. Chem., 311, 36 (2009); doi:10.1016/j.molcata.2009.06.020.
Y.L.N. Murthy, B.S. Diwakar, B. Govindh, K. Nagalakshmi, I.V. Kasi Viswanath and R. Singh, J. Chem. Sci., 124, 639 (2012); doi:10.1007/s12039-012-0258-9.
C. Perez, M. Pauli and P. Bazevque, Acta Biologiae et Medicine Experimentalis, 15, 113 (1990).
M.A. Pfaller, M. Castanheira, D.J. Diekema, S.A. Messer, G.J. Moet and R.N. Jones, J. Clin. Microbiol., 48, 1592 (2010); doi:10.1128/JCM.02445-09.
Clinical Laboratory Standards Institute Methods for Dilution Antimicrobial Susceptibility Test for Bacteria That Grow Aerobically; Approved Standard M 07-A9, edn 9, vol. 32, No. 2, p. 12 (2012).
J.-M. Yang, J. Comput. Chem., 25, 843 (2004); doi:10.1002/jcc.20013.
J.M. Yang and C.C. Chen, Proteins, 55, 288 (2004); doi:10.1002/prot.20035.
A. Bekaert, J. Andrieux and M. Plat, Tetrahedron Lett., 33, 2805 (1992); doi:10.1016/S0040-4039(00)78863-0.
K. Venkatesan, S.S. Pujari, R.J. Lahoti and K.V.C. Srinivasan, Ultrason. Sonochem., 15, 548 (2008); doi:10.1016/j.ultsonch.2007.06.001.