Synthesis 2022; 54(13): 3085-3092
DOI: 10.1055/s-0041-1737414
paper

Rapid and Facile Synthesis of Isomaleimides: Dehydration of Maleamic Acids using Methanesulfonyl Chloride

Khyarul Alam
,
Elvis C. McFee
,
This research was supported by the National Science Foundation (CAREER­ CHE-1351883) and the College of Arts & Sciences at the University of North Carolina at Greensboro.


Abstract

The dehydration of maleamic acids using methanesulfonyl chloride as a dehydrating agent to selectively and rapidly (<15 min) generate isomaleimides is reported. A variety of maleamic acid derivatives produce the corresponding isomaleimides in good to excellent yields. Adaptation of this protocol under flow synthesis allows for similar efficiency and decreased reaction times (13 seconds residence time). It was also possible to convert maleic anhydride into the desired isomaleimide in a two-step, one-flask operation.

Supporting Information



Publikationsverlauf

Eingereicht: 27. Januar 2022

Angenommen nach Revision: 28. Februar 2022

Artikel online veröffentlicht:
07. April 2022

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