Cyanuric chloride: decent dehydrating agent for an exclusive and efficient synthesis of kinetically controlled isomaleimides |
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Authors: | Kishan P. Haval Narshinha P. Argade |
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Affiliation: | Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India |
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Abstract: | Starting from maleanilic 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, isophtalimide in 91% yield, while the corresponding succinanilic acid furnished the thermodynamically more stable succinimide in high yield. |
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Keywords: | Maleamic acids Cyanuric chloride Dehydration Kinetic products Isomaleimides |
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