Document Type: Original Research Article

Authors

1 Department of Science, Payame Noor University (PNU), PO Box: 19395-4697, Tehran, Iran

2 Department of Chemistry, Payame Noor University, P. O. Box 19395-3697, Tehran, Iran.

Abstract

An efficient construction of 2-(N-arylamino)benzaldehydes and N-aryl-3,10-dihydroacridin-1(2H)-one derivatives starting from 2- hydroxybenzaldehydes has been developed. The synthesis of N-aryl-3,10-dihydroacridin-1(2H)-ones is based on the Knoevenagel condensation of dimedone to various 2-(N-arylamino)benzaldehydes, followed by an intramolecular enamination in the presence of 20 mol% of nanocrystalline ZnO. Moderate to high yields, operation simplicity, and cheap starting materials are the key features of the present method. The structures of the products were confirmed by 1H and 13C NMR spectroscopy and mass spectrometry (EI). Probable mechanisms for the present reactions to account for the formation of 2-(N-arylamino)benzaldehydes 3a-h and N-aryl-3,10-dihydroacridin-1(2H)-one derivatives 4a-h are also reported.

Graphical Abstract

Keywords

Main Subjects

[1]               X.Y. Hu, J.C. Zhang, W. Wei, J.X. Ji, Tetrahedron Lett.,2011, 52, 2903-2905.

[2]               H. Takahash, Y. Bekkali, A.J. Capolino, T. Gilmore, S.E. Goldrick, P.V. Kaplita, L. Liu, R.M. Nelson, D. Terenzio, Z.L. Wang, J. Proudfoot, G. Nabozny, D Thomson, Bioorg. Med. Chem. Lett., 2007, 17, 5091-5095.

[3]                N.A. Petasis, A.N. Butkevich, J. Organometal. Chem., 2004, 694, 1747-1753.

[4]               K. Makino, O. Hara, Y.Takiguchi, T. Katano, Y.Asakawa, K.Hatano, Y. Hamada, Tetrahedron Lett., 2003, 44, 8925-8929.

[5]                T. Aono, T.Doi, K.Fukatsu, JP Patent 042823701992 A2, 1992.

[6] F.I. Carroll, J.T. Blackwell,  A. Philip, C.E. Twine, J. Med. Chem.,1976, 19, 1111-1119.

[7] J.S.Yadav, B.V.S. Reddy, K.Premalatha, M.S.R.Murty, J. Mol. Catal. A, 2007, 271, 161-163.

[8] I.V. Ukrainets, P.A.Rezugly, S.G.Taran, O.V.Gorokbova, A.V.Turov, Tetrahedron Lett., 1995, 36, 7747-7750.

[9] T.K. Jones, D.T. Winn, L.Zhi, L.G.Hamann, C.M.Tegley, C.L.F. Pooley, US Patent, 5, 688, 808, 1997.

[10]           J.N. Kim, H.S. Kim, J.H. Gong, Y.M. Chung, Tetrahedron Lett., 2001, 42, 8341-8344.

[11]           G. Lu, H.C. Malinakova, J. Org. Chem., 2004, 69, 4701-4715.

[12]           A.R. Katrizky, S.Rachwal, B.Rachwal, Tetrahedron, 1996, 52, 15031-15070.

[13]           S.W. Elmore, M.J.Coghlan, D.D. Anderson, J.K. Pratt, B.E. Green, A.X. Wang, M.A. Stashko, C.W. Lin, C.M. Tyree, J.N. Miner, P.B. Jacobson, D.M. Wilcox, B.C. Lane, J. Med. Chem., 2001, 44, 4481-4491.

[14]           P. Bandyopadhyay, M. Sathe, P. Sharma, M.P. Kaushik, Tetrahedron Lett., 2012, 53, 4631-4635.

[15]           S. Pal, S. Durgadas, S.B. Nallapati, K. Mukkanti, R. Kapavarapu, C.L.T. Meda, K.V.L. Parsa, M. Pal, Bioorg. Med. Chem. Lett., 2011, 21, 6573-6576.

[16]           F.K.L. El-Hady, M.S.  Abdel-Aziz, K.H. Shaker, Z.A. El-Shahid, L.S. Ibrahim, Int. J. Pharm. Sci. Rev. Res.,2015, 30, 272-278.

[17]           B.M. Gutsulyak, M.V. Melnik, A.D.  Kachkovskii, Chem. Heterocycl. Compd., 1999, 35, 875-876.

[18]           R. Martinez, G. Espinosa-Perez, M. Brito-Arias, J. Chem. Crystallogr., 1995, 25, 201-203.

[19]           C. Beaudry, S. Allaoui,  Res. Policy, 2012, 41, 1589-1606.

[20]           A. Khataee, R. Darvishi, Ch. Soltani, A. Karimi, S.W. Joo, Ultrason. Sonochem., 2015, 23, 219-230.  

[21]           A. Kołodziejczak-Radzimska, T. Jesionowski,  Materials, 2014, 7, 2833-2881.

[22]           F.M. Moghaddam, Z. Mirjafary, M.J. Javan, S. Motamen, H. Saeidian, TetrahedronLett., 2014, 55, 2908-2911.  

[23]           M.Z. Kassaee, F. Movahedi, H. Masrouri, Synlett, 2009, 1326-1330.

[24]           S. Sadjadi, M. Eskandari, Monatsh. Chem.,2012, 143, 653-656.

[25]           M. Gupta, S. Paul, R. Gupta, A. Loupy, Tetrahedron Lett., 2005, 46, 4957-4960.

[26]           M. Hosseini-Sarvari, M. Tavakolian, Appl. Catal.A,2012, 441–442, 65-71.

[27]           M. Hosseini-Sarvari, H. Sharghi, J. Org. Chem., 2006, 71, 6652-6654.

[28]           F. Tamaddon, F. Aboee, A. Nasiri, Catal. Commun., 2011, 16, 194-197.

[29]           R. Tayebee, F. Javadi, E. Rezaei-Seresht, S.J. Ahmadi, M. Hosseinpour, B. Maleki., Indust. Engin. Chem. Res. 2012, 51, 13577-13582.

[30]           P. Bhattacharyya, K. Pradhan, S. Paul, A.R. Das, Tetrahedron Lett., 2012, 53, 4687-4691.

[31]           F.M. Moghaddam, H. Saeidian, Mater. Sci. Eng. B, 2007, 139, 265-269.

[32]           Z. Mirjafary, H. Saeidian, A. Sadeghi, F.M. Moghaddam, Catal. Commun., 2008, 9, 299-306.

[33]           H. Saeidian, Z. Mirjafary. E. Abdolmaleki, F. Moradnia, Synlett,2013, 2127-2131.

[34]           H. Saeidian, A. Sadeghi, Z. Mirjafary, F.M. Moghaddam, Synthetic Commun., 2008, 38, 2043-2053.

[35]           H. Yang, Z.B. Li, D.S. Shin, L.Y. Wang, J.Z. Zhou, H.B. Qiao, X. Tian, M.Y. Ma, H. Zuo, Synlett, 2010, 483-489.

[36]           H. Saeidian, F.M. Moghaddam, A. Pourjavadi, S. Barzegar, R. Soleyman, A. Sohrabi, J. Braz. Chem. Soc., 2009, 20, 466-471.

[37]           B. Karami, M. Kiani, Catal. Commun., 2011, 14, 62-67.

[38]           O.O. Fadeyi, S.T.  Adamson, E.L. Myles, C.O. Okoro, Bioorg. Med. Chem. Lett., 2008, 18, 4172-4176.

[39] U.U. Indulkar, S.R.  Kale, M.B. Gawande, R.V. Jayaram, Tetrahedron Lett.,2012, 53, 3857-3860.