Synthesis and biological activity of nitrogen heterocycles from anthranilic acid derivative

S. S. El-Sakka¹, M.A.E. Hashash¹, I.I. Abd El-Gawad¹ and G. E. Ahmed²

¹Department of Chemistry, Faculty of Science, Ain Shams University, Cairo (Egypt). ²Department of Chemistry, Faculty of Science, Suez Canal University, Suez (Egypt).

ABSTRACT:

Reaction of 2-phenyl-6,8-dibromo-3,1-benzoxazine-4-one (1) with benzoylhydrazine, hydroxylamine, ammonia and sodium azide gave the corresponding 6,8-dibromo-3-substituted- 4(3H)quinazolinones (2, 3 and 8), tetrazole derivative (6) and 1-benzoylbenzimidazole-2-one. Acetylation and alkylation of 3 with acetyl chloride and ethyl chloroactate yielded the corresponding 3-substituted- 4(3H)-quinazolinones (4 and 5). Chlorination of 8 with POCl3/ PCl5 afforded the corresponding 4- chloro-6, 8-dibromoquinazoline (9). Treatment of 9 with mercapto compounds, aromatic amines, piperidine and active methylene compounds gave the corresponding 4-substituted quinazolines (10, 11, 12 and 14). Reaction of 9 with thiourea, sodium azide and hydrazine hydrate yielded the corresponding 4(3H)-quinazoline-4-thione (13), tetrazolo quinazoline (15) and 4-hydrazino-quinazoline (16). Triazoloquinazoline (18) was prepared via cyclocondensation of compound 16 with carbon disulphide in presence of alcoholic potassium hydroxide. Some synthesized compounds also exhibited antimicrobial activities.

KEYWORDS:

Synthesis; biological activity; nitrogen heterocycles

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Copy the following to cite this article: El-Sakka S. S, Hashash M. A. E, El-Gawad I. I. A, Ahmed G. E. Synthesis and biological activity of nitrogen heterocycles from anthranilic acid derivative. Orient J Chem 2009;25(2).

Copy the following to cite this URL: El-Sakka S. S, Hashash M. A. E, El-Gawad I. I. A, Ahmed G. E. Synthesis and biological activity of nitrogen heterocycles from anthranilic acid derivative. Available from: http://www.orientjchem.org/?p=11383