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.
el-Khamry
A M
AM
Chemistry Department, Faculty of Science, Ain Shams University, Abbasia, Cairo.
el-Nagdy
S
S
Habashy
M M
MM
el-Bassiouny
F A
FA
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