Synthesis and reactions of some biologically active 2-(2'-thienyl)benzoxazinone and quinazolinone derivatives.
Different amines were found to attack the hitherto unknown 6,8-dibromo-2-(2'-thienyl)-3,1-benzoxazin-4(H)-one (2) entirely at position-4, producing the corresponding benzamide derivatives 3a-i. Compound 2 reacted with hydrazoic acid affording the tetrazole 5, beside the benzimidazole derivative 6. Similarly carbon nucleophiles, such as ethyl acetoacetate attack 2 to give 7. 6,8-Dibromo-2(2'-thienyl)-4(3H)-quinazoline and its 3-substituted derivatives 8 a-g were also synthesized. Theoretical calculations for the benzoxazinone 2 and others, based on the simple HMO-method were performed. Close accordance between the theoretically predicted reactivities and the experimental findings was obtained. Biological activities of some of the compounds obtained were also tested.
Chemistry Department, Faculty of Science, Ain Shams University, Abbasia, Cairo.
A M
AM
el-Khamry
S
S
el-Nagdy
M M
MM
Habashy
F A
FA
el-Bassiouny
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001419:Bacteria / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D008826:Microbial Sensitivity Tests; D010078:Oxazines / Q000138:chemical synthesis* / Q000494:pharmacology; D011799:Quinazolines / Q000138:chemical synthesis* / Q000494:pharmacology; D013876:Thiophenes / Q000138:chemical synthesis* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D010078:Oxazines; D011799:Quinazolines; D013876:Thiophenes