Journal
MOLECULAR DIVERSITY
Volume 21, Issue 1, Pages 69-79Publisher
SPRINGER
DOI: 10.1007/s11030-016-9698-3
Keywords
gamma-spiroiminolactones; gamma-Dispiroiminolactones; Parabanic acid derivatives; Dialkyl acetylenedicarboxylates; Isocyanide; Zwitterionic intermediate
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Funding
- Research Council of Mazandaran University
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A direct entry and simple process for the synthesis of -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 -disubstituted urea and thiourea with oxalyl chloride, then a three-component reaction was carried out with isocyanides, acetylenic esters, and -disubstituted parabanic acid derivatives. The method allows the construction of a variety of -spiroiminolactone structures in good to high yields starting from readily available precursors. It was found that in the case of -diphenyl thioparabanic acid, additional products of -dispiroiminolactones have been formed due to the higher electrophilicity of -dicarbonyl groups. The structures were fully established using spectroscopic analysis NMR, IR, and Mass spectrometry. The crystal structure of -dispiroiminolactone was confirmed from single-crystal X-ray diffraction study.
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