SciELO - Scientific Electronic Library Online

 
vol.65Synthesis, characterization and antimicrobial studies of some novel 1,3,4-thiadiazolium-2-thiolate derivativesAn investigation of the interaction between resazurin and Cd2+ and Zn2+ ions in aqueous medium índice de autoresíndice de assuntospesquisa de artigos
Home Pagelista alfabética de periódicos  

Serviços Personalizados

Journal

Artigo

Indicadores

    Links relacionados

    • Em processo de indexaçãoCitado por Google
    • Em processo de indexaçãoSimilares em Google

    Compartilhar


    South African Journal of Chemistry

    versão On-line ISSN 1996-840Xversão impressa ISSN 0379-4350

    S.Afr.j.chem. (Online) vol.65  Durban  2012

     

    RESEARCH ARTICLE

     

    SnO2/SiO2 nanocomposite catalyzed one-pot, four-component synthesis of 2-amino-3-cyanopyridines

     

     

    Ajeet A. Yelwande; Madhukar E. Navgire; Deepak T. Tayde; Balasaheb R. Arbad; Machhindra K. Lande*

    Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad (M.S.), 431004, India

     

     


    ABSTRACT

    An efficient and rapid protocol for the synthesis of 2-amino-3-cyanopyridines by the cyclocondensation reaction of aromatic aldehydes, methyl ketones, malononitrile and ammonium acetate catalyzed by SnO2/SiO2 nanocomposite material at refluxed condition in ethanol was investigated. Nanocomposite (SnO2/SiO2) catalytic material has been synthesized by using the sol-gel method. The prepared catalytic materials were characterized by using X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive spectroscopy (EDS), Fourier transform infrared spectroscopy (FT-IR), Brunauer-Emmer-Teller (BET) surface area, and temperature-programmed desorption of ammonia (NH3-TPD). Advantages of the present method include a simple work-up procedure, high yields of the products, low toxicity and easy recovery and reusability of the catalytic materials.

    Keywords: : SnO2/SiO2, sol-gel, nanocomposite, 2-amino-3-cyanopyridines, heterogeneous catalyst


     

     

    Full text available only in PDF format.

     

    Acknowledgements

    The authors thank the Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, India, for providing laboratory facilities, and the DST for providing financial help under the DST-FIST scheme.

     

    References

    1 R. Summitt, J.A. Marley and N.F. Borrelli, J. Phys. Chem. Solids., 1964, 25, 1465-1469.         [ Links ]

    2 T.W. Kim, D.U. Lee, D.C. Choo, J.H. Kim, H.J. Kim, J.H. Jeong,M. Jung, J.H. Bahang H.L. Park, Y.S. Yoon and J.Y. Kim, J. Phys. Chem. Solids., 2002, 63, 881-885.         [ Links ]

    3 T.E. Moustafid, H. Cachet, B. Tribollet and D. Festy, Electrochim. Acta., 2002, 47, 1209-1215.         [ Links ]

    4 M. Okuya, S. Kaneko, K. Hiroshima, I. Yagi and K. Murakami, J. Eur. Ceram. Soc., 2001, 21, 2099-2102.         [ Links ]

    5 F.L. Chen and M.L. Liu, Chem. Commun., 1999, 47, 1829-1830.         [ Links ]

    6 C. Kim, M. Noh, M. Choi, J. Cho and B. Park, Chem. Mater., 2005, 17, 3297-3301.         [ Links ]

    7 A.J. Moulson and J.M. Herbert, Electroceramics, Chapman & Hall New York 1990.         [ Links ]

    8 Y. Shimizu and M. Egashira, MRS. Bull., 1999, 24, 18-24.         [ Links ]

    9 H.C. Wang, Y. Li and M. J. Yang, Sens. Actuators. B. Chem., 2006, 119, 380-383.         [ Links ]

    10 G.J. Li, X.H. Zhang and S. Kawi, Sens. Actuators. B. Chem., 1999, 60, 64-70.         [ Links ]

    11 Z.W. Chen, J.K.L. Lai and C.H. Shek, Phys. Rev. B., 2004, 70, 165314-1-165314-7.         [ Links ]

    12 A. Dieguez, A. Rodriguez, R.A. Vila and J.R. Morante, J. Appl. Phys., 2001, 90, 1550-1557.         [ Links ]

    13 T. Arai, J. Phys. Soc. Jpn, 1960, 15, 916-927.         [ Links ]

    14 J. Jeong, S.P. Choi, C.I. Chang, D.C. Shin, J.S. Park, B.T. Lee, Y.J. Park and H.J. Song, Solid. State. Commun, 2003, 127, 595-597.         [ Links ]

    15 L.R.B. Santos, T. Chartier, C. Pagnoux, J.F. Baumard, C.V Santilli, S.H. Pulcinelli and A. Larbot, J. Eur. Ceram. Soc., 2004, 24, 3713-3721.         [ Links ]

    16 B. Grzeta, E. Tkalcec, C. Goebbert, M. Takeda, M. Takahashi, K. Nomura and M. Jaksic, J. Phys. Chem. Solids., 2002, 63, 765-772.         [ Links ]

    17 J.A.T. Antonio, R.G. Baez, P.J. Sebastian and A. Vazquez, J. Solid. State. Chem., 2003, 174, 241-248.         [ Links ]

    18 J. Zhang and L. Gao, J. Solid. State. Chem, 2004, 177, 1425-1430.         [ Links ]

    19 V.A. Sadykov, S.N. Pavlova, S.N. Saputina, I.A. Zolotarskii, N.A. Pakhomov, E.M. Moroz, V.A. Kuzmin and A.V. Kalinkin, Catal. Today 2000, 61, 93-99.         [ Links ]

    20 A. Hagemeyer, Z. Hogan, M. Schlichter, B. Smaka, G. Streukens, H. Turner, J.A. Volpe, H. Weinberg and K. Yaccato, Appl. Catal. A. Gen., 2007, 317, 139-148.         [ Links ]

    21 A.E.R.S. Khder, Appl. Catal. A. Gen., 2008, 343, 109-116.         [ Links ]

    22 J. Li, J. Hao, L. Fu, Z. Liu and X. Cui, Catal. Today 2004, 90, 215-221.         [ Links ]

    23 R. Gavagnin, L. Biasetto, F. Pinna and G. Strukul, Appl. Catal. B. Env., 2002, 38, 91-99.         [ Links ]

    24 D.Y. Zhao, P.D. Yang, Q.S. Huo, B.F. Chmelka and G.D. Stucky, Solid State Mater. Sci., 1998, 3, 111-121.         [ Links ]

    25 Y. Ren, L.P. Qian, B. Yue, and H.Y. He, Chin. J. Catal., 2003, 24, 947-950.         [ Links ]

    26 S.X. Liu, B. Yue, J. Rao, Y. Zhou and H.Y. He, Mater. Lett., 2006, 60, 154-158.         [ Links ]

    27 K.F. Lam, K.L. Yeung, and G. McKay, Environ. Sci. Technol., 2007, 41, 3329-3334.         [ Links ]

    28 M.S. Park, G.X. Wang, Y.M. Kang, S.Y. Kim, H.K. Liu and S.X. Dou, Electrochem. Commun., 2007, 9, 71-75.         [ Links ]

    29 C. Temple, G.A. Rener, W.R. Waud and P.E. Noker, J. Med. Chem., 1992, 35, 3686-3690.         [ Links ]

    30 H.M. Kanjariya, T.V Radhakrishnan, K.R. Ramchandran and P Hansa, Indian. J. Chem. Sect. B., 2004, 43, 1569-1573.         [ Links ]

    31 K.H. Popat, V.V. Kachhadia, K.S. Nimavat and H.S.J. Joshi, Indian. Chem. Soc., 2004, 81, 157-159.         [ Links ]

    32 S. Jurgen, G. Siegfried, S. Alexander, B. Horst, B. Martin, G. Rainer, H. Siegbert and H. Joachim, Howard-Paul R US Patent, 1995, 5432282.         [ Links ]

    33 T. Murata, M. Shimada, H. Kadono, S. Sakakibara, T. Yoshino, T. Masuda, M. Shimazaki, T. Shintani, K. Fuchikami, K.B. Bacon, K.B. Ziegelbauer and T.B. Lowinger, Bioorg. Med. Chem. Lett., 2004, 14, 4013-4017.         [ Links ]

    34 J.K. Landguist, Comprehensive Heterocyclic Chemistry, Pergamon, Oxford, UK, 984, 155.         [ Links ]

    35 A.S. Girgis, A. Kalmouch, H.M. Hosni, Amino Acids 2004, 26, 139-146.         [ Links ]

    36 S. Kambe, K. Saito, Synthesis 1980, 366-368.         [ Links ]

    37 F. Shi, S. Tu, F. Fang and T. Li, Arkivoc 2005, 1, 137-142.         [ Links ]

    38 E.V Tret'yakova, O.B. Flekhter, F.Z. Galin, L.V. Spirikhin and G.A. Tolstikov, Russ. J. Org. Chem., 2003, 39, 1738-1740.         [ Links ]

    39 A.M. Shestopalov and O.A. Naumov, Russ. Chem. Bull., 2003, 52, 1380-1385.         [ Links ]

    40 A.N. Vasiliev, Y.S. Kayukov, O.E. Nasakin, A.N. Lyshchikov, V.N. Nesterov, O.V. Kayukova and O.V. Poulkherovskaya, Chem. Heterocycl. Compd., 2001, 37, 309-314.         [ Links ]

    41 S.R. Sarda, J.D. Kale, S.K. Wasmatkar, V.S. Kadam, P.G. Ingole, W.N. Jadhav, R.P. Pawar, Mol. Divers., 2009, 13, 545 549.         [ Links ]

    42 J. Tang, L. Wang, Y. Yao, L. Zhang, W Wang, Tetrahedron Lett, 2011, 52, 509 511.         [ Links ]

    43 A.A. Yelwande, B.R. Arbad and M.K. Lande, S. Afr. J. Chem., 2010, 63, 199-203.         [ Links ]

    44 S.B. Rathod, M.K. Lande and B.R. Arbad, Bull. Korean Chem. Soc, 2010, 31, 2835-2840.         [ Links ]

    45 A.A. Yelwande B.R. Arbad and M.K. Lande, J. Korean Chem. Soc., 2011, 55, 644-649.         [ Links ]

    46 G.J. McCarthy and J.M. Welton, Powder. Diffr., 1989, 4, 156-159.         [ Links ]

    47 S. Gnanam and V. Rajendran, Digest. J. Nanomaterials. Biostructures., 2010, 5, 699-704.         [ Links ]

    48 Y. Wang, C. Ma, X. Sun and H. Li, Nanotechnol, 2002, 13, 565-569.         [ Links ]

    49 N.G. Deshpande, Y.G. Gudage, J.C. Ramphal Sharma Vyas, J.B. Kim and Y.P. Lee, Sens. Actuators. B. Chem., 2009, 138, 76-84.         [ Links ]

     

     

    Received 6 December 2012
    Revised 14 February 2012
    Accepted 4 June 2012

     

     

    * To whom correspondence should be addressed. E-mail: mkl_chem@yahoo.com