柯蒂斯重排
化学
苯甲酸酯
烷基
叠氮化物
邻苯二甲酸酐
水解
药物化学
苯甲酸
有机化学
催化作用
作者
Mostafà Khouili,M. Dolors Pujol,Hasna Yassine,Jamila Bouali,Asmaa Oumessaoud,El Mahdi Ourhzif,Salha Hamri,Abderrafia Hafid
出处
期刊:Synthesis
[Georg Thieme Verlag KG]
日期:2021-01-11
卷期号:53 (11): 1971-1979
被引量:2
标识
DOI:10.1055/s-0040-1706643
摘要
Abstract The 2-(alkylcarbonyl)benzoic acids obtained by esterification of phthalic anhydride are converted into azide derivatives: alkyl 2-[(azidocarbonyl)amino]benzoates and to ureas: dialkyl 2,2′-[carbonylbis(azanediyl)]dibenzoates. These transformations were carried out using classical Curtius rearrangement conditions in the presence of diphenylphosphoryl azide (DPPA) in a basic medium, followed by hydrolysis. Subsequently, a final condensation reaction of these urea derivatives enabled us to obtain, for the first time, the new alkyl derivatives, alkyl 2-[2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl]benzoates. All the new compounds obtained in satisfactory yields were characterized by 1H and 13C NMR, and by X-ray crystallographic analysis.
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