【摘 要】
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Evodiamine is one of the most important components of Evodia rutaecarpa,which has been used for a long time in traditional medicine.In this work,we developed an efficient gold-catalyzed strategy to co
【机 构】
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State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemi
【出 处】
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中国化学会第十三届全国有机合成化学学术研讨会
论文部分内容阅读
Evodiamine is one of the most important components of Evodia rutaecarpa,which has been used for a long time in traditional medicine.In this work,we developed an efficient gold-catalyzed strategy to construct the skeletons of evodiamine analogues from 2-(2-(N-methylindole))-3-propargylquinazolinone (1).It was found that substrate 1 underwent an AuCl3-catalyzed cyclization/isomerization to give the evodiamine scaffold 2 bearing a seven-member ring in moderate yields.While it would provide evodiamine scaffold 3 bearing a six-member ring in high yields if the substrate 1 went through an initial oxidation by DDQ in the same reaction conditions.The reaction was compatible with various functional groups including halides,methoxy or methyl substituents.The experiment results revealed that the sp2 or sp3 hybrid of the carbon atom in the quinazolinone moiety played an important role on constructing these two kinds of evodiamine analogue.
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