Polyethylene Glycol (PEG-400): As Efficient Reaction Medium for the Synthesis of 1,5-Dihydropyrano[2,3-c]chromene Derivatives

Document Type : Original Article

Authors

1 Pharmaceutics Research Center, Institute of Neuropharmacology, Kerman University of Medical Sciences

2 Pharmaceutics Research Center, Institute of Neuropharmacology, Kerman University of Medical Sciences, Kerman, Iran

Abstract

In this research, a simple and effective method for the synthesis of 1,5-dihydropyrano[2,3-c]chromene multi-substituted derivatives has been introduced, using the three-component reaction of aromatic aldehydes, malononitrile and 3-hydroxycoumarin at room temperature and in the presence of polyethylene glycol (PEG-400) as solvent and reaction catalyst. Easy method, short reaction time, high atom economy, high yields, environmental acceptability and the easy of separating of polyethylene glycol are included as the most important advantages of this method. Moreover, the produced products were obtained through simple filtering and no need to column and technique chromatography with high purity. Moreover, the produced products were obtained through simple filtering and no need to column and technique chromatography with high purity.

Keywords

Main Subjects


[1] J. Zhu, Multicomponent Reactions. Germany, Wiley-VCH: Weinheim (2005).
[2] L.F. Tietze, Chem. Rev. 96 (1996) 115.
[3] L.F. Tietze, U. Beifuss, Angew. Chem. 105 (1993) 137.
[4] D.A. Horton, G.T. Bourne and M.L. Smythe, Chem. Rev. 103 (2003) 893.
[5] S. Damavandi, R. Sandaroos, Heterocycl. Commun. 17 (2011) 187.
[6] R. Sharma, G. Veera, D. Bandaru, R.K. Someswara, R.M. Veeraghava, K.A. Kumar and B. Cherukuvada, Heterocycl. Commun. 21 (2015) 187.
[7] A. Rezvanian, M.M. Heravi, Z. Shaabani and M. Tajbakhsh, Tetrahedron. 73 (2017) 2009.

[8] A. Kumar, R.A. Maurya, S.A. Sharma, P. Ahmad, A.B. Singh, G. Bhatia, and A.K. Srivastava, Bioorg. Med. Chem. Lett. 19 (2009) 6447.

[9] T. Raj, R.K. Bhatia, A. Kapur, M. Sharma, A.K. Saxena and M.P.S. Ishar, Eur. J. Med. Chem. 45 (2010) 790.

[10] T. Symeonidis, K.C. Fylaktakidou, D.J. Hadjipavlou-Litina and K.E. Litinas, Eur. J. Med. Chem. 44 (2009) 5012.
[11] T. Raj, R.K. Bhatia, M. Sharma, V. Gupta, D. Sharma, M.P.S. Ishara, Eur. J. Med. Chem. 44 (2009) 3209.
[12] M. Ough, A. Lewis, E.A. Bey, J. Gao, J.M. Ritchie, W. Bornmann, D.A. Boothman, L.W. Oberley, and J. Cullen, Cancer Biol. Ther. 4 (2005) 95.

[13] V.F. De Andrade-Neto, M.O.F. Goulart, J.F. Da Silva Filho, M.J. Da Silva, M.D.F.R. Pinto,  A.V. Pinto, M.J. Zalis, L.H. Carvalho, and A.U. Krettli, Bioorg. Med. Chem. Lett. 14 (2004) 1145.

[14] G.P. Ellis, In The Chemistry of Heterocyclic Compounds Chromenes, Chromanes and Chromones, New York, J. Wiley and Sons (1977).
[15] E.A. Hafez, M.H. Elnagdi, A.G.A. Elagemey and F.M.A.A. El-Taweel, Heterocycles 26 (1987) 903.
[16] T.J. Dickerson, N.N. Reed and K.D. Janda, Chem. Rev. 102 (2002) 3325.
[17] B. Das, V.S. Reddy and M. Krishnaiah, Tetrahedron Lett. 47 (2006) 8471.

[18] L. Nagarapu, R. Mallepalli, L. Yeramanchi and R. Bantu, Tetrahedron Lett. 52 (2011) 3401.

[19] B. Das, P. Balasubramanyam, G.C. Reddy and N. Salvanna, Helv. Chim. Acta 94 (2011) 1347.

[20] H. Paidepala, S. Nagendra, V. Saddanappu, A. Addlagatta and B. Das, Med. Chem. Res. 23 (2014) 1031.

[21] R. Mallepalli, D.K.R. Vennam and R.S. Perali, Tetrahedron Lett. 57 (2016) 4541.

[22] S.Y. Ebrahimipour, M. Abaszadeh, J. Castro and M. Seifi,  Polyhedron, 79 (2014) 138.

[23] M. Abaszadeh and M. Seifi, Res. Chem. Intermed. 41 (2015) 7715.
[24] M. Abaszadeh, M. Seifi and S.Y. Ebrahimipour, Bull. Chem. Soc. Ethiop. 30 (2016) 253.
[25] S. M. Vahdat, M. Khavarpour and F. Mohanazadeh, Journal of Applied Chemistry. 9 (2015) 41.

[26] S. Paul, P. Bhattacharyya and A.R. Das, Tetrahedron Lett. 52 (2011) 4636.

[27] S. Paul, S. Ghosh, P. Bhattacharyya and A.R. Das, RSC Adv. 3 (2013) 14254.

[28] A. Kale, C. Bingi, S. Sripada, C.G. Kumar and K. Atmakur, Bioorganic & Medicinal Chemistry Letters. 26 (2016) 4899.

[29] D. Azarifar, O. Badalkhani, Y. Abbasi and M. Hasanabadi, J Iran Chem Soc. 14 (2017) 403.

[30] M.N. Elinson, F.V. Ryzhkov, R.F. Nasybullin, A.N. Vereshchagin, and M.P. Egorov, Helv. Chim. Acta. 99 (2016) 724.

[31] M.N. Khan, S. Karamthulla, L. H. Choudhury and M.S.H. Faizib, RSC Adv. 5 (2015) 22168.