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Synthesis 2023; 55(09): 1441-1450
DOI: 10.1055/s-0042-1751406
paper

A Novel Ring-Opening/Ring-Closing Cascade Reaction Selectively Induced by Aliphatic Primary Amine Using Phenolic Hydroxyl as a Traceless Directing Group

Shuntao Huang
a   National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming, 650500, P. R. of China
,
Teng Liu∗
b   College of Chemistry and Environmental Science, Qujing Normal University, Qujing, 655011, P. R. of China
,
Jingpeng Li
a   National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming, 650500, P. R. of China
,
Qi Yang
a   National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming, 650500, P. R. of China
,
Shuyan Zhan
a   National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming, 650500, P. R. of China
,
Chao Huang  ∗
a   National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming, 650500, P. R. of China
› Author AffiliationsThis work was supported by the National Natural Science Foundation of China (Nos. 21662046 and 21202142), the Yunnan Local Colleges Research Projects of China (No. 202101BA070001-049), and the Program of Innovative Research Team (in science and technology) in University of Yunnan Province and Scientific and Technological Innovation Team for Green Catalysis and Energy Material in Yunnan Institutions of Higher Learning.
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Abstract

An interesting ring-closing/ring-opening cascade reaction selectively induced by aliphatic primary amine for the synthesis of functionalized aminomaleimides is described. This work features phenolic hydroxyl as a traceless directing group that forms a critical six-membered intermediate and then a lactone ammonolysis/intramolecular amidation sequence. This two-step, one-pot practical protocol has broad substrate scope (39 examples) and delivers structurally diverse aminomaleimides in good to excellent yields.

Key words

aminomaleimides - ring-closing/ring-opening reaction - aliphatic primary amines - phenolic hydroxyl - directing group

Supporting Information



Publication History

Received: 25 November 2022

Accepted after revision: 14 December 2022

Article published online:
12 January 2023

© 2023. Thieme. All rights reserved

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