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South African Journal of Chemistry

On-line version ISSN 1996-840X
Print version ISSN 0379-4350

S.Afr.j.chem. (Online) vol.63  Durban  2010

 

RESEARCH ARTICLE

 

Polyaniline/SiO2 catalyzed one-pot synthesis of tetrahydrobenzo[b]pyran derivatives

 

 

Ajeet A. Yelwande; Balasaheb R. Arbad; Machhindra K. Lande*

Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, (MS) - 431 004, India

 

 


ABSTRACT

Polyaniline/SiO2 is an efficient catalyst for the synthesis of tetrahydrobenzo[b]pyran derivatives from a one-pot, three component, condensation of aldehydes, malononitrile and dimedone at room temperature. This protocol has several advantages such as high yield, a simple work up procedure, low toxicity and easy recovery and reusability of the catalytic material. The catalyst has been readily prepared and characterized by means of thermal analysis (TG-DTA), X-ray diffraction (XRD), scanning electron microscopy (SEM) and Fourier transform infrared spectroscopy (FT-IR).

Keywords: Chemical oxidative method, Polyaniline/SiO2, tetrahydrobenzo[b]pyran


 

 

Full text available only in PDF format.

 

Acknowledgements

The authors are grateful to the Head ot the Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, India, for providing the laboratory facility.

 

References

1 A.G. MacDiarmid, Synth. Met., 1997, 84, 27.         [ Links ]

2 Y. Cao, S. Li, Z, Xue and D. Guo, Synth. Met., 1986, 16, 305.         [ Links ]

3 R. Noufi, A.J. Nozik, J. White and L.F. Warren, J. Electrochem. Soc., 1982, 129, 2261.         [ Links ]

4 W. Westerweele, P. Smith and A.J. Heeger, Adv. Mater., 1995, 7, 788.         [ Links ]

5 A.F. Diaz and J.A. Logan, J. Electroanal. Chem., 1980, 111, 111.         [ Links ]

6 A.Watanabe, K. Mori, A. Iwabuchi, Y. Iwasaki, Y. Nakamuraand and O. Ito, Macromolecules, 1989, 22, 3521.         [ Links ]

7 W.W. Focke, G.E. Wnek and Y. Wei, J. Phys. Chem., 1987, 91, 5813.         [ Links ]

8 J. Prokes and J. Stejskal, Polym. Degrad. Stab, 2004, 86, 187.         [ Links ]

9 S. Velusamy, M. Ahmed and T. Punniyamurthy, Org. Lett., 2004, 6, 4821        [ Links ]

10 C.L. Devi, O.S. Olusegun, C.N.S.S. Pavankumar, V.J. Rao and S. Palaniappan, Catal. Lett., 2009, 132, 480.         [ Links ]

11 C. Srinivas, C.N.S.S. Pavankumar, V.J. Rao and S. Palaniappan,. J. Mol. Catal. A. Chem, 2007, 265, 227.         [ Links ]

12 A.Q. Zhang, N. Zhang, S. HongandM. Zhang, Synth. Commun, 2009, 39, 3024.         [ Links ]

13 S. Palaniappan, C. Saravanan, C.A. Amarnatha and VJ. Rao, Catal. Lett., 2004, 97, 1.         [ Links ]

14 A.L. Patel, H.R. Talele, H.S. Rama and A.V. Bedekar, Synth. Commun., 2009, 39, 3016.         [ Links ]

15 M.L. Kantam, M. Roy, S. Roy, B. Sreedhar, M.S. Sakunthala, B.M. Choudaryb and R. Lal, Tetrahedron, 2007, 63, 8002.         [ Links ]

16 P. Srinivasan and S.R. Malladi, Green. Chem, 2002, 4, 53.         [ Links ]

17 S. Hatakeyama, N. Ochi, H. Numata and S. Takano, J. Chem. Soc. Chem. Commun., 1988, 17, 1202.         [ Links ]

18 R. Gonzalez, N. Martin, C. Seoane, J.L. Marco, A. Albert and F.H. Cano, Tetrahedron Lett., 1992, 33, 3809.         [ Links ]

19 W.O. Foye, Principal di Chemico Farmaceutica, Piccin, Padova, Italy, 1991, 416.         [ Links ]

20 D. Armesto, W.M. Horspool, N. Martin, A. Ramos and C. Seaone, J. Org. Chem., 1989, 54, 3069.         [ Links ]

21 K. Singh, J. Singh and H. Singh, Tetrahedron, 1996, 52, 14273.         [ Links ]

22 A. Shaabani, S. Samadi, Z. Baderi and A. Rahmati, Catal. Lett., 2005, 104, 39.         [ Links ]

23 S. Abdolmohammadi and S. Balalaie, TetrahedronLett, 2007, 48, 3299.         [ Links ]

24 Pawar, Synth. Commun., 2007, 37, 4353.         [ Links ]

25 X.Z. Lian, Y.Huang, YQ. Liand WJ. Zheng Monatsh. Chem.,2008, 139, 129.         [ Links ]

26 R. Hekmatshoar, S. Majedi and K. Bakhtiari, Catal. Commun., 2008, 9, 307.         [ Links ]

27 T.S. Jin, A.Q. Wang, F. Shi, L.S. Han, L.B. Liu and TS. Li, ARKIVOC, 2006,14, 78.         [ Links ]

28 L. Fotouhi, M.M. Heravi, A. Fatehi and K. Bakhtiari, Tetrahedron Lett., 2007, 48, 5379.         [ Links ]

29 I. Devi, B.S.D. Kumar and P.J. Bhuyan, Tetrahedron Lett., 2003, 44, 8307.         [ Links ]

30 G. Sabitha, K. Arundhathi, K. Sudhakar, B.S. Sastry, J.S. Yadav, Synth. Commun., 2009, 39, 433.         [ Links ]

31 S.S. Katkar, P.H. Mohite, L.S. Gadekar, B.R. Arbad and M.K. Lande, Centr. Euro. J. Chem., 2010, 8, 320.         [ Links ]

32 S.S. Katkar, P.H. Mohite, L.S. Gadekar, B.R. Arbad, K.N. Vidhate and M.K. Lande, Chin. Chem. Lett., 2010, 21, 421.         [ Links ]

33 S.B. Rathod, B.R. Arbad and M.K. Lande, Chin. J. Catal., 2010, 31, 631-636.         [ Links ]

34 S.B. Rathod, B.R. Arbad, A.B. Gambhire and M.K. Lande, Bull. Korean. Chem. Soc., 2010, 31, 339.         [ Links ]

35 Y.Q. Li, S.Y. Fu, Y. Yang and Y.W. Mai, Chem. Mater., 2008, 20, 2637.         [ Links ]

36 S.C. Raghavendra, S. Khasim, M. Revanasiddappa, M.VN. Ambika Prasad and A.B. Kulkarrni, Bull. Mater. Sci., 2003, 26, 733.         [ Links ]

37 M.A. Ali, E. Saion, N. Yahya, A. Kassim, K.M. Dahlan and S. Hashim, J. Eng. Sci. Technol, 2007, 2, 111.         [ Links ]

 

 

Received 20 August 2010
Revised 27 October
Accepted 19 November 2010

 

 

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

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