Ammonium monovanadate: a versatile and reusable catalyst for Friedel-Crafts alkylation and Michael addition of indoles

Iranian Journal of Catalysis

مقاله 7، دوره 4، شماره 2، شهریور 2014، صفحه 105-111   

نوع مقاله: Articles

نویسنده

Kobra Nikoofar^*

Department of Chemistry, Faculty of Science, Alzahra University, Vanak, 1993893973 Tehran, Iran

چکیده

Ammonium monovanadate (NH4VO3) has been devoted as an efficient, commercially available, eco-friendly and reusable catalyst for the synthesis of bis(indolyl)methanes (BIMs), oxindole derivatives and also Michael adducts of indoles at 50 °C under solvent-free conditions. The reusability of this solid acid catalyst in addition with its selectivity has also been examined.

کلیدواژه‌ها

Indole؛ Isatin؛ α؛ β-Unsaturated compounds؛ Alkylation؛ Ammonium monovanadate

مراجع

[1] A. Baeyer, A. Emmerling, Ber. Dtsch. Chem. Ges. 2 (1869) 679-682.

[2] R.J. Sundberg, The Chemistry of indoles, Academic press, New York, 1970.

[3] R.K. Brown, in Indoles, W.J. Houlihan (ed.), Wiley-Interscience, New York, 1972.

[4] G.W. Gribble, in Comprehensive heterocyclic chemistry II, Vol. 2, A.R. Katritzky, C.W. Ress, E.F.V. Scriven, C.W. Bird (eds.), Pergamon Press, Oxford 1996, p 207-221.

[5] R.J. Sundberg, in Comprehensive heterocyclic chemistry, Vol. 4, A.R. Katritzky, C.W. Ress (eds.), Pergamon Press, Oxford, 1984.

[6] J.A. Joule, in Science of synthesis, Houben-Weyl methods of molecular transformations, Vol. 10, E.J. Thomas (ed.), George Thieme Verlag, Stuttgart, Germany, 2000.

[7] F.R. Chen, J. Huang, Chem. Rev. 105 (2005) 4671-4706.

[8] X. Ge, S. Yanni, G. Rennert, N. Gruener, F.A. Fares, Biochem. Biophys. Res. Commun. 228 (1996) 153-158.

[9] S. Foldeak, J. Czumbas, B. Matkovics, Acta Univ. Szeged. Acta Phys. Chem. 11 (1965) 15-121.

[10] J. Porszasz, G.P. Katalin, S. Foldeak, B. Matkovics, Acta Physical. Acad. Sci. Hunt. 29 (1996) 299-305.

[11] G.W. Gribble, in Top. Heterocycl. Chem. Vol. 26, Springer-Verlag, Berlin, Heidelberg, 2010.

[12] M.A. Zeiligs, J. Med. Food 1 (1998) 67-82.

[13] F. D. Pope, J. Heterocyl. Chem. 21 (1984) 1641-1645.

[14] K.C. Joshi, V.N. Pathak, S.K. Jain, Pharmazie 35 (1980) 677-679.

[15] F. Garrido, J. Ibanez, E. Gonalons, A. Giraldez, Eur. J. Med. Chem. 12 (2004) 3923-3930.

[16] G.W. Gribble, J. Chem. Soc. Perkin Trans. 1 (2000) 1045-1075.

[17] M. Shiri, Chem. Rev. 112 (2012) 3508-3549.

[18] M. Shiri, M.A. Zolfigol, G.H. Kruger, Z. Tanbakouchian, Chem. Rev. 110 (2010) 2250-2293.

[19] M. Bandini, A. Eichholzer, Angew. Chem. Int. Ed.48 (2009) 9608-9644.

[20] A. Cacchi, G. Fabrizi, Chem. Rev. 111 (2011) PR215-PR283.

[21] M. Jeganathan, K. Kanagaraj, A. Dhakshinamoorthy, K. Pitchumani, Tetrahedron Lett. 55 (2014) 2061-2064.

[22] R.R. Jella, R. Nagarajan, Tetrahedron 69 (2013) 10249-10253.

[23] M. Shiri, J. Iran Chem. Soc. 10 (2013) 1019-1023.

[24] V. Synecek, F.Hanic, Czech. J. Phys. 4 (1954) 120-129.

[25] J.M. Stellman, in Encyclopedia of occupational health and safety, 4^th ed. Vol. III, Geneva, 1998, p 43.

[26] T. Garcia, B. Solsona, D.M. Murphy, K.L. Antcliff, S.H. Taylor, J. Catal. 229 (2005) 1-11.

[27] S.S. Sonar, A.A.H. Kategaonkar, A.M.N. Ware, C.H. Gill, B.B. Shingate, M.S. Shingare, Arkivoc ii (2009) 138-148.

[28] S.A. Sadaphal, A.H. Kategaonkar, S.B. Sapkal, B.B. Shingate, C.H. Gill, M.S. Shingare, Bull. Catal. Soc. India 8 (2009) 131-139.

[29] T. Moriuchi, K. Kikushima, T. Kajikawa, T. Hirao, Tetrahedron Lett. 50 (2009) 7385-7387.

[30] P.G. Mandhane, R.S. Joshi, A.R. Ghawalkar, G.R. Jadhav, C.H. Gill, Bull. Korean Chem. Soc. 30 (2009) 2969-2972.

[31] I. Mohammadpoor-Baltork, H.R. Memarian, A.R. Khosropour, K. Nikoofar, Lett. Org. Chem. 3 (2006) 768-772.

[32] I. Mohammadpoor-Baltork, H.R. Memarian, A.R. Khosropour, K. Nikoofar, Heterocycles 68 (2006) 1837-1843.

[33] H.R. Memarian, I. Mohammadpoor-Baltork, K. Nikoofar, Can. J. Chem. 85 (2007) 930-937.

[34] M.M. Khodaei, I. Mohammadpoor-Baltork, H.R. Memarian, A.R. Khosropour, K. Nikoofar, P. Ghanbary, J. Heterocyclic Chem. 45 (2008) 377-381.

[35] H.R. Memarian, I. Mohammadpoor-Baltork, K. Nikoofar, Ultrason. Sonochem. 15 (2008) 456-462.

[36] L. Fotouhi, K. Nikoofar Tetrahedron Lett. 54 (2013) 2903-2905.

[37] S.F. Hojati, K. Nikoofar, Z. Etemadifar, Iran. Chem. Commun. 1 (2013) 25-31.

[38] K. Nikoofar, Chem. Sci. Trans. 2 (2013) 691-700.

[39] J. Azizian, H. Fallah-Bagher-Shaidaei, H. Kefayati, Synth. Commun. 33 (2003) 789-793.

[40] R.R. Nagawade, D.B. Shinde, Acta Chim. Slov. 53 (2006) 210-213.

[41] S. Kamble, G. Rashinkar, A. Kumbhar, R. Salunkhe, Synth. Commun. 42 (2012) 756-766.

[42] N. Seyedi, M. Kalantari, J. Sci. I. R. Iran 24 (2013) 205-208.

[43] R. Ghorbani-Vaghei, H. Veisi, H. Keypour, A.A. Dehghani-Firouzabadi, Mol. Divers. 14 (2010) 87-96.

[44] A. Hasaninejad, A. Zare, H. Sharghi, Kh. Niknam, M. Shekouhy, Arkivoc xiv (2007) 39-50.

[45] P. Hazarika, S.D. Sharma, D. Konwar, Synth. Commun. 38 (2008) 2870-2880.

[46] R. Tayebee, F. Nehzat, E .Rezaei-Seresht, F.Z. Mohammadi, E. Rafiee, J. Mol. Catal. A: Chem. 351 (2011) 154-164.

[47] J.S. Yadav, B.V.S. Reddy, Ch.V.S.R. Murthy, G.M. Kumar, Ch. Madan, Synthesis (2001) 783-787.

[48] J.S. Yadav, S. Abraham, B.V.S. Reddy, G. Sabitha, Synthesis (2001) 2165-2169.

[49] S.J. Jin, S.Y. Wang, Synlett (2003) 2074-2076.