The reaction of 2-(trifluoromethyl)-3,1-benzoxazone with amines was studied. At first, when one mole equivalent of 2-(trifluoromethyl)-3,1-benzoxazone was treated with one mole equivalent of phenylenediamine afforded bis-benzamide derivatives rather than 3-(aminophenyl)quinazolinone derivatives. Many trials to obtain the 3-(aminophenyl)quinazolinones were carried out, and the final result is that it is difficult to obtain the 3-(aminophenyl)quinazolinones in acceptable yield and purity from the reaction of phenylenediamine with 2-(trifluoromethyl)-benzoxazinone. The synthesis of new 6-iodo-3-substituted-2-(trifluoromethyl)quinazolin-4(3H)-one derivatives was studied as follows: when the 6-iodo-2-(trifluoromethyl)-3,1-benzoxazin-4-one was fused with some amines at 140 °C for 10 min, it afforded 5-iodo-N-(methyl and aryl)-2-(trifluoroacetamido)benzamide derivatives. While, when 6-iodo-2-(trifluoromethyl)-3,1-benzoxazinone was condensed with the same amines in acetic acid under reflux conditions, it afforded 6-iodo-3-(methyl and aryl)-2-(trifluoromethyl)quinazolin-4(3H)-one derivatives. Condensation of the 6-iodo-2-(trifluoromethyl)-3,1-benzoxazinone with hydrazine hydrate gave 3-amino-6-iodo-2-(trifluoromethyl)quinazolinone. Condensation of the latter 3-aminoquinazolinone with some aldehydes and isatin afforded the corresponding Schiff's bases. The expected antimicrobial properties of the synthesized compounds were investigated. Most of the compounds showed moderate effects on some bacteria. Most compounds had no effects on fungi. Schiff's base of isatin showed the best results among all the tested compounds. The latter Schiff's base showed potent activity, like ketoconazole toward fungi.

Graphical abstract

中文翻译：

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6-碘-2-(三氟甲基)-4(3H)-喹唑啉酮衍生物的合成及其抗菌活性

研究了2-(三氟甲基)-3,1-苯并恶腙与胺的反应。首先，当用一摩尔当量的苯二胺处理一摩尔当量的2-(三氟甲基)-3,1-苯并恶腙时，得到双苯甲酰胺衍生物而不是3-(氨基苯基)喹唑啉酮衍生物。为了获得3-(氨基苯基)喹唑啉酮进行了多次尝试，最终的结果是，由苯二胺与2-(三氟甲基)-反应以可接受的产率和纯度获得3-(氨基苯基)喹唑啉酮是困难的。苯并恶嗪酮。新型6-碘-3-取代-2-(三氟甲基)喹唑啉-4(3 H )-酮衍生物的合成研究如下：当6-碘-2-(三氟甲基)-3,1-苯并恶嗪- 4-酮与一些胺在140℃下稠合10分钟，得到5-碘-N- (甲基和芳基)-2-(三氟乙酰氨基)苯甲酰胺衍生物。而当6-碘-2-(三氟甲基)-3,1-苯并恶嗪酮与相同的胺在乙酸中在回流条件下缩合时，得到6-碘-3-(甲基和芳基)-2-(三氟甲基)喹唑啉-4(3 H )-酮衍生物。 6-碘-2-(三氟甲基)-3,1-苯并恶嗪酮与水合肼缩合得到3-氨基-6-碘-2-(三氟甲基)喹唑啉酮。后者的3-氨基喹唑啉酮与一些醛和靛红的缩合得到相应的席夫碱。研究了合成化合物的预期抗菌特性。大多数化合物对某些细菌表现出中等影响。大多数化合物对真菌没有影响。在所有测试的化合物中，靛红希夫碱显示出最好的结果。后者希夫碱显示出强大的活性，就像酮康唑对真菌的作用一样。

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