Document Type: Original Research Article

Authors

1 Department of Chemistry, Payame Noor University, Abhar, Iran

2 Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, IRAN

Abstract

An efficient and convenient synthesis of novel tetrahydrobenzo[c]acridin-8(7H)-one derivatives is described using the electrogenerated anion of acetonitriles as the base in the presence of tetrabutylammonium fluoride as an effective supporting electrolyte in a one-pot, three-component condensation of aromatic aldehyde, dimedone and 1-naphthyl amine. The reaction is carried out in an undivided cell containing an iron cathode and a graphite anode under a constant current density of 5 mA/cm2 (I=20 mA, electrode surface=5 cm2) in CH3CN at room temperature was found to be optimum for the electrochemically induced chain process and resulted in the highest yield.
An efficient and convenient synthesis of novel tetrahydrobenzo[c]acridin-8(7H)-one derivatives is described using the electrogenerated anion of acetonitriles as the base in the presence of tetrabutylammonium fluoride as an effective supporting electrolyte in a one-pot, three-component condensation of aromatic aldehyde, dimedone and 1-naphthyl amine. The reaction is carried out in an undivided cell containing an iron cathode and a graphite anode under a constant current density of 5 mA/cm2 (I=20 mA, electrode surface=5 cm2) in CH3CN at room temperature was found to be optimum for the electrochemically induced chain process and resulted in the highest yield.

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[1] B.B. Tour, D.G. Hall, Chem. Rev., 2009, 109, 4439-4486.

[2] G.J. Finaly, G.J. Atwell, B.C. Baguley, Oncol. Res., 1999, 11, 249-254.

[3] H.H. Lee, W.R. Wilson, D.M. Ferry, P. van Zijl, S.M. Pullen, W.A. Denny, J. Med. Chem., 1996, 39, 2508-2517.

[4] D.G. Carole, D.M. Michel, C. Julien, D. Florence, N. Anna, J. Séverine, D. Gérard, T.D. Pierre, G. Jean-Pierre, Bioorg. Med. Chem., 2005, 13, 5560–5568.

[5] P.F. Bousquet, M.F. Braňa, D. Conlon, K. Fitzgerald, M.D. Perron, C. Cocchiaro, R. Miller, M. Moran, J. George, X.D. Qian, G. Keilhauer, C.A. Romerdahl, Cancer Res., 1995, 55, 1176–1189.

[6] M.F. Branňa, M. Cacho, A. Gradillas, B. Pascual-Teresa, A. Ramos, Curr. Pharm. Des., 2001, 7, 1745–1780.

[7] P. Yang, Q. Yang, X. Qian, L. Tong, X. Li, J. Photochem. and Photobio. B: Biology, 2006, 84, 221–226.

[8] N. Martin, M. Quinteiro, C. Saoane, L. Mora, M. Saure, E. Ockoa, A. Morales, J. Hetrocycl. Chem., 1995, 51, 235-238.

[9] X.S. Wang, M.M. Zhang, Z.S. Zeng, D.Q. Shi, S.J. Tu, Z.Y. Wei, Z.M. Zong, Arkivoc., 2006, 117-123.

[10] T.S. Jin, J.S. Zhang, T.T. Guo, A.Q. Wang, T.S. Li, Synthesis, 2004, 12, 2001-2005.

[11] M.R. Poor Heravi, P. Aghamohammadi, C. r. Chimie, 2012, 15, 448-453.

[12] H. Zang, Y. Zhang, Y. Zang, B.-W. Cheng, Ultrason. Sonochem., 2010, 17 (3), 495–499.

[13] H. Zang, Y. Zhang, Y. Mo, B. Cheng, Synth. Commun., 2011, 41 (21), 3207–3214.

[14] E. Cortes, R. Martinez, J.G. Avila, R.A. Toscano, J. Hetrocycl. Chem., 1988, 25, 895-899.

[15] V. Nadaraj, S.T. Selvi, S. Mohan, Eur. J. Med. Chem., 2009, 44, 976-980.