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3-羟基氧化吲哚与异亚丙基丙二腈的DBU催化迈克尔-平纳异构化串联反应:合成含完全取代二氢呋喃基序的高官能化双螺氧化吲哚

A DBU-catalyzed Michael-Pinner-isomerization cascade reaction of 3-hydroxyoxindoles with isatylidene malononitriles: access to highly functionalized bispirooxindoles containing a fully substituted dihydrofuran motif.

作者信息

Zhu Yan-Shuo, Wang Wen-Bo, Yuan Bei-Bei, Li Ya-Ning, Wang Qi-Lin, Bu Zhan-Wei

机构信息

College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, China.

出版信息

Org Biomol Chem. 2017 Jan 25;15(4):984-990. doi: 10.1039/c6ob02254e.

Abstract

The first DBU-catalyzed Michael/Pinner/isomerization cascade reaction of 3-hydrooxindoles with isatylidene malononitriles was developed, and the corresponding highly functionalized bispirooxindoles containing a fully substituted dihydrofuran motif were obtained in up to 92% yields. This protocol also provides an efficient method for the synthesis of an α-cyano-γ-butyrolactone bispirooxindole. In addition, a one-pot three-component cascade reaction was conducted. Also, the asymmetric version of the cascade reaction was achieved.

摘要

首次开发了3-羟基吲哚与异亚丙基丙二腈的DBU催化的迈克尔/平纳/异构化串联反应,以高达92%的产率得到了含有完全取代二氢呋喃基序的相应高度官能化双螺环氧化吲哚。该方法也为α-氰基-γ-丁内酯双螺环氧化吲哚的合成提供了一种有效方法。此外,还进行了一锅三组分串联反应。并且,实现了该串联反应的不对称版本。

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