TRANSFORMATION OF BENZOXAZINONE DERIVATIVES TO SOME INTERESTING HETEROCYCLIC COMPOUNDS WITH EXPECTED BIOLOGICAL ACTIVITY

• Published in: Heterocycles Vol. 91; no. 7; pp. 1399 - 1416
• Main Authors: Marzouk, Magda I., Farghaly, Thoraya A., E-Hashash, Maher A., Shaker, Soheir A., Hussein, Shadia M.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier 2015
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology
• ISSN: 0385-5414; 1881-0942
• DOI: 10.3987/COM-15-13218

The newly synthesized iodobenzoxazinone derivative was reacted with benzoyl hydrazide, sodium azide, hydrazine hydrate, p-toluidine, hydroxylamine hydrochloride and formamide to give (quinazolinyl)benzamide, (oxazinyl)benzohydrazide, imidazolecarboxamide, (tetrazolyl)benzoic acid, 3-aminoquinazolinone, p-toylquinazolinone, hydroxyquinazolinone and quinazolinone derivatives respectively. Reaction of hydroxyquinazolinone with acetic anhydride and ethyl chloroacetate afforded (quinazolinyl)acetate and ethyl (quinazolinyloxy) acetate derivatives. The quinazolinone reacted with benzoyl chloride, acetyl chloride and ethyl chloroacetate to afford N-(3-benzoyl-dihydroquinazolinyl)-N-phenylbenzamide, 3-acetylquinazolinone and ethyl quinazolinylacetate respectively. The acetohydrazide which was synthesized from the reaction of the ethyl quinazolinyl acetate with hydrazine hydrate was used as a starting material for preparation of some other quinazolinone derivatives. The newly synthesized compounds were characterized by spectroscopic tools and some of them were screened for antibacterial and antifungal activity.