Journal
TETRAHEDRON
Volume 62, Issue 5, Pages 937-942Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.10.027
Keywords
maleamic acids; cyanuric chloride; dehydration; kinetic products; isomaleimides
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Starting from maleanitic and maleamic acids, a facile general approach to kinetically controlled isomaleimides has been described for the first time using cyanuric chloride as a dehydrating agent with 85-98% yields. The effect of a variety of substituents present on the aromatic ring in amine and maleic anhydride moiety, on these kinetic/thermodynamic dehydration processes of anilic acids has been also described. Under the same set of reaction conditions the phthalanilic acid gave kinetically controlled product, isoplitalimide in 91% yield, while the corresponding succinanilic acid furnished the thermodynamically more stable succinimide in high yield. (c) 2005 Elsevier Ltd. All rights reserved.
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