A Fast and Efficient Method for the Synthesis of 1,5-Benzodiazepine Derivatives Under Solvent-Free Conditions

Document Type: Research Article

Authors

Department of Chemistry, Shahid Beheshti University, P.O. Box 19396-4717 Tehran, I.R. IRAN

Abstract

Silica sulfuric acid is found to catalyze efficiently the condensation of o-phenylenediamines with various linear and cyclic ketones to afford the corresponding 1,5-benzodiazepines in quantitative yields under solvent-free conditions at room temperature

Keywords

Main Subjects


[1] Randall, L. O. and Kappel, B., In "Benzodiazepines", Garattini, S., Mussini, E. and Randall, L. O., Eds., Raven Press: New York, pp. 27-51 (1973).

[2] Schutz, H., "Benzodiazepines", Springer: Heidelberg (1982).

[3] Landquist, J. K., In "Comprehensive Heterocyclic Chemistry", Katritzky, A. R. and Rees, C. W., Eds., Pergamon: Oxford, Vol. 1, p. 166 (1984).

[4] DeBaun, J. R., Pallos, F. M. and Baker, D. R., US Patent, 3 978 227 (1976).

[5] Essaber, M., Baouid, A., Hasnaoui, A., Benharref, A. and Lavergne, J. P., Synth. Commun., 28, 4097 (1998).

[6] El-Sayed, A. M., Abdel-Ghany, H. and El-Saghier, A. M. M., Synth. Commun., 29, 3561 (1999).

[7] Reddy, K. V. V., Rao, P. S. and Ashok, D., Synth. Commun., 30, 1825 (2000).

[8] Ried, W. and Stahlofen, P., Chem. Ber., 90, 815 (1957).

[9] Ried, W. and Torinus, E., Chem. Ber., 92, 2902 (1959).

[10] Pozarentzi, M., Stephanidou-Stephanatou, J. and Tsoleridis, C. A., Tetrahedron Lett., 43, 1755 (2002).

[11] Thakuria, H., Pramanik, A., Borah, B. M. and Das, G., Tetrahedron Lett., 47, 3135 (2006).

[12] Jung, D. I., Choi, T. W., Kim, Y. Y., Kim, I. S., Park, Y. M., Lee, Y. G. and Jung, D. H., Synth. Commun., 29, 1941 (1999).

[13] Das, B., Reddy, M. R., Ramu, R., Reddy, K. R. and Geethangili, M., J. Chem. Res. (S), 598 (2005).

[14] Herbert, J. A. L. and Suschitzky, H., J. Chem. Soc., Perkin Trans., I, 2657 (1974).

[15] Curini, M., Epifano, F., Marcotullio, M. C. and Rosati, O., Tetrahedron Lett., 42, 3193 (2001).

[16] Yadav,  J. S.,  Reddy,  B. V. S.,  Praveen  Kumar, S. and Nagaiah, K., Synthesis, 480 (2005).

[17] Bangdar,  B. P., Bettigeri,  S. V. and Joshi, N. S., Synth. Commun., 34, 1447 (2004).

[18]  Chen, W. Y. and Lu, J., Synlett, 8, 1337 (2005).

[19] Chari, M. A. and Syamasundar, K., Cat. Commun., 6, 67 (2005).

[20] De, S. K. and Gibbs, R. A., Tetrahedron Lett., 46, 1811 (2005).

[21] Reddy, B. M. and Sreekanth, P. M., Tetrahedron Lett., 44, 4447 (2003).

[22] Yadav, J. S., Reddy, B. V. S., Eshwaraiah, B. and Anuradha, K., Green. Chem., 4, 592 (2002).

[23] Jarikote, D.V., Siddiqui, S. A., Rajagopal, R., Daniel, T., Lahoti, R. J. and Srinivasan, K. V., Tetrahedron Lett., 44, 1835 (2003).

[24] Morales, H. R., Bulbarela, A. and Contreras, R., Heterocycles, 24, 135 (1986).

[25] Das, B., Ramu, R., Ravikanth, B. and Reddy, V. S., J. Mol. Catal.  A-Chem., 246, 76 (2006).

[26] Balakrishna, M. S. and Kaboudin, B., Tetrahedron Lett., 42, 1127 (2001).

[27] Tajbakhsh, M., Heravi, M. M., Mohajerani, B. and Ahmadi, A. N., J. Mol. Catal. A-Chem., 247, 213 (2006).

[28] Yadav, J. S., Reddy, B. V. S., Praveenkumar, S., Nagaiah, K., Lingaiah, N. and Saiprasad, P. S., Synthesis, 6, 901 (2004).

[29] Varala, R., Enugala, R., Nuvula, S. and Adapa, S. R., Synlett., 7, 1009 (2006).

[30] Zolfigol, M. A., Tetrahedron, 57, 9509 (2001).

[31] Shaabani, A., Bazgir, A., Teimouri, F. and Lee, D. G., Tetrahedron Lett., 43, 5165 (2002).

[32] Shaabani, A., Teimouri, F. and Lee, D. G., Synth. Commun., 33, 1057 (2003).

[33] Shaabani, A. and Lee, D. G., Synth. Commun., 33, 1255 (2003).

[34] Shaabani, A., Soleimani, K. and Bazgir, A., Synth. Commun., 34, 3303 (2004).

[35] Shaabani, A., Soleimani, E. and Badri, Z., Monatsh. Chem., 137, 181 (2006).

[36] Shaabani, A. and Rahmati, A., J. Mol. Catal. A-Chem., 249, 246 (2006).