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MICROWAVE ENHANCED SYNTHESIS OF QUINAZOLINES |
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[a0023]
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MICROWAVE ENHANCED SYNTHESIS OF QUINAZOLINES |
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Julio A. Seijas*, M. Pillar Vázquez-Tato* and M. Montserrat Martínez
Received: 5 August 1999 / Uploaded: 22 August 1999
Microwave heating has been employed as a frequent resource for improvement of classical reactions, and sometimes it led to discover new reactions. Quinazolines are a kind of compounds well known, whose synthesis has been studied for more than a century.
In this paper we describe the use of microwaves to enhance the synthesis
of 4-aminoquinazolines. These compounds are of interest due to its pharmacological uses.
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When anthranilonitrile is heated in a domestic microwave oven in the presence of potassium tert-butoxide, 2-(2-aminophenyl)-4-aminoquinazoline2(3a) is isolated in good yield (60%). If the above reaction was carried out using a heating mantle, the transformation proceeded sluggishly.
Mixed couplings were also assayed, thus when we heated together anthranilonitrile and benzonitrile the reaction product was 3b in a 53% yield. Meanwhile, in mixed couplings of anthranilonitrile (1) with salicylonitrile (2c) and with o-methoxynitrile (2d) no quinazoline could be isolated. At the present we are studying the influence of different aromatic rings with several substitution patterns in compound 2.
We think our method constitutes an easy way to deal with the synthesis of variety of quinazolines, opening a via to check new applications of this compounds as bioactive agents.
Acknowledgments
We thank Dirección General de Enseñanza Superior (DGES) for its financial support (PB96-0936).
1.- "The Merck Index", Budavari, S., Editor. Merck & Co., Inc. 12th.ed. Whitehouse Station, N.J., 1996.
2.- Partridge, M. W., Stevens, M. F. G., J. Chem. Soc. 1964, 3663.
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