Abstract
The interest of microwaves in drug discovery and multi-step synthesis is exposed with the aim of describing our strategy. These studies are connected with our work on the synthesis of original heterocycliccompounds with potential pharmaceutical value. Reactions in the presence of solvent and solvent-free synthesis can be realised under a variety of conditions; for some of these selected results are given, and where available, results from comparison with the same solvent-free conditions but with classical heating are given.
Similar content being viewed by others
References
For recent books: (a) Loupy, A. (ed.),tiMicrowaves in Organic Synthesis, Wiley-VCH Verlag Gmbh & Co. KGaA, Weinhein, 2002.
Hayes, B. L.,tiMicrowave Synthesis: Chemistry at the Speed of Light, CEM Publishing, Matthews (U.S.A.), 2002.
Chabane, H., Lamazzi, C., Thiéry, V., Pierré, A., Léonce, S., Pfeiffer, B., Renard, P., Guillaumet, G. and Besson, T., Synthesis and cytotoxic evaluation of novel thiazolocarbazoles, Part II, J. Enz. Inh. Med. Chem., 18 (2003) 167–174.
Lamazzi, C., Chabane, H., Thiéry, V., Pierré, A., Léonce, S., Pfeiffer, B., Renard, P., Guillaumet, G. and Besson, T., Synthesis and cytotoxic evaluation of novel thiazolocarbazoles, J. Enz. Inh. Med. Chem., 17 (2002) 397–401.
Chabane, H., Lamazzi, C., Thiéry, V., Guillaumet, G. and Besson, T., Synthesis of novel 2-cyanothiazolocarbazoles analogues of ellipticine, Tetrahedron Lett., 43 (2002) 2483–2486.
Besson, T. and Guillard, J., Synthesis of novel dioxinobenzothiazole derivatives, Tetrahedron, 55 (1999) 5139–5144.
Bénéteau, V., Besson, T., Guillard, J., Leonce, S. and Pfeiffer, B., Synthesis and in vitro antitumour evaluation of benzothiazole-2-carbonitrile derivatives, Eur. J.Med. Chem., 34 (1999) 1053–1060.
Molinski T. F., Marine pyridoacridine alkaloids: structure and biological chemistry, Chem. Rev., 93 (1993) 1825–1838.
Gunawardana, G. P., Kohmoto, S., Gunasekara, S. P., McConnel O. J. and Koehn F. E., Dercitin, a new biologically active acridine alkaloid from a deep water sponge marine sponge, Dercitus sp., J. Am. Chem. Soc., 110 (1988) 4856–4858.
Gunawardana, G. P., Kohmoto S. and Burres, N. S., New cytotoxic acridine alkaloids from two deep water marine sponges of the family Pachastrellidae, Tetrahedron Lett., 30 (1989) 4359–4362.
Sengupta, S. K., ‘Topoisomerase II Inhibitors’, in W. O. Foye (ed.),tiCancer Chemotherapeutic Agents, ACS Professional Reference Books, Washington DC, 1995, pp. 246–260.
Bénéteau, V., Besson, T. and Rees, C. W., Rapid synthesis of 2-cyanobenzothiazoles from N-aryliminodithiazoles under microwave irradiation, Synth. Commun., 27 (1997) 2275–2280.
English, R. F., Rakitin, O. A., Rees, C. W. and Vlasova, O. G., Conversion of imino-1,2,3-dithiazoles into 2-cyanobenzothiazoles, cyanoimidoyl chlorides and diatomic sulphur, J. Chem. Soc., Perkin Trans. 1, (1997) 201–205.
Besson, T. and Rees, C. W., Some chemistry of 4,5-dichloro-1,2,3-dithiazolium chloride and its derivatives, J. Chem. Soc., Perkin Trans. 1, (1995) 1659–1662.
Appel, R., Janssen, H., Siray, M. and Knoch, F., Syntheses und reacktionen des 4,5-dichlor-1,2,3-dithiazolium chlorids, Chem. Ber., 118 (1985) 1632–1643.
Frère, S., Thiéry, V., Bailly, C. and Besson, T., Novel 6-substituted benzothiazol-2-yl indolo[1,2-c]quinazolines and benzimidazo[1,2-c]quinazolines, Tetrahedron, 59 (2003) 773–779.
Besson, T., Dozias, M. J., Guillard, J., Jacquault, P., Legoy, M. D. and Rees, C. W., Microwave irradiation in the presence of solvent: expeditious routes to 4-alkoxyquinazoline-2-carbonitriles and thiocarbamates via N-arylimino-1,2,3-dithiazoles, Tetrahedron, 54 (1998) 6475–6484.
Besson, T., Dozias, M. J., Guillard, J. and Rees, C. W., New route to 2-cyanobenzothiazoles via N-arylimino-1,2,3-dithiazoles, J. Chem. Soc., Perkin Trans. 1, (1998) 3925–3926.
Von Niementowski, S., Synthesen von chinazolinverbindungen, J. Prakt. Chem., 51 (1895) 564–572.
Alexandre, F. R., Berecibar, A. and Besson, T., Microwaveassisted Niementowski reaction – Back to the roots, Tetrahedron Lett., 43 (2002) 3911–3913.
Laporterie, A., Marquié, J. and Dubac, J., ‘Microwaveassisted Reactions on Graphite’, in A. Loupy (ed.),tiMicrowaves in Organic Synthesis, Whiley-VCH Verlag Gmbh & Co. KGaA, Weinhein, 2002, pp. 219–252.
Soukri, M., Guillaumet, G., Besson, T., Aziane, D., Aadil, M., Essassi, El. M. and Akssira, M., Synthesis of novel 5a,10,14b,15-tetraaza-benzo[a]indeno[1,2-c] anthracen-5-one and benzimidazo[1,2-c]quinazoline derivatives under microwave irradiation, Tetrahedron Lett., 41 (2000) 5857–5860.
Domon, L., Le Coeur, C., Grelard, A., Thiéry, V. and Besson, T., Efficient modified von Niementowski synthesis of novel derivatives of 5a,14b,15-triazabenzo[a]indeno[1,2-c]anthracen-5-one from indolo[1,2-c]quinazoline, Tetrahedron Lett., 42 (2001) 6671–6674.
Besson, T., Guillard, J. and Rees, C. W., Multi-step synthesis of thiazoloquinazolines under microwave irradiation in solution, Tetrahedron Lett., 41 (2000) 1027–1030.
Alexandre, F. R., Berecibar, A., Wrigglesworth, R. and Besson, T., Efficient synthesis of thiazoloquinazolinone derivatives, Tetrahedron Lett., 44 (2003) 4455–4458.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Alexandre, FR., Domon, L., Frère, S. et al. Microwaves in drug discovery and multi-step synthesis. Mol Divers 7, 273–280 (2003). https://doi.org/10.1023/B:MODI.0000006860.56083.2b
Issue Date:
DOI: https://doi.org/10.1023/B:MODI.0000006860.56083.2b