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• 作者：Sakineh Asghari ; Mohammad Qandalee ; Amir Ali Sarmadi
• 关键词：\(\upgamma \) ; spiroiminolactones ; \(\upgamma \) ; Dispiroiminolactones ; Parabanic acid derivatives ; Dialkyl acetylenedicarboxylates ; Isocyanide ; Zwitterionic intermediate
• 刊名：Molecular Diversity
• 出版年：2017
• 出版时间：February 2017
• 年：2017
• 卷：21
• 期：1
• 页码：69-79
• 全文大小：
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Biochemistry, general; Organic Chemistry; Polymer Sciences; Pharmacy;
• 出版者：Springer International Publishing
• ISSN：1573-501X
• 卷排序：21

文摘

A direct entry and simple process for the synthesis of \(\upgamma \)-spiroiminolactones present in a large number of natural products has been developed. In the first step, the synthesis of parabanic acid derivatives was commenced from the reaction of \(\textit{N}{,}{} \textit{N}^{\prime }\)-disubstituted urea and thiourea with oxalyl chloride, then a three-component reaction was carried out with isocyanides, acetylenic esters, and \(\textit{N}{,}{} \textit{N}^{\prime }\)-disubstituted parabanic acid derivatives. The method allows the construction of a variety of \(\upgamma \)-spiroiminolactone structures in good to high yields starting from readily available precursors. It was found that in the case of \(\textit{N}{,}{} \textit{N}^{\prime }\)-diphenyl thioparabanic acid, additional products of \(\upgamma \)-dispiroiminolactones have been formed due to the higher electrophilicity of \(\upalpha \)-dicarbonyl groups. The structures were fully established using spectroscopic analysis NMR, IR, and Mass spectrometry. The crystal structure of \(\upgamma \)-dispiroiminolactone was confirmed from single-crystal X-ray diffraction study.