Metal-free, I2-promoted direct synthesis of 2-cyano-substituted maleimides via a unique 3,3-dicyano-2-arylacrylic acid intermediate?
Organic & Biomolecular Chemistry Pub Date: 2022-12-13 DOI: 10.1039/D2OB01725C
Abstract
A robust, I2-mediated cyclization reaction was developed for the synthesis of 2-cyano-substituted maleimides from arylethylidene malononitriles and amines via unique a 3,3-dicyano-2-arylacrylic acid intermediate. The reaction duration was short and devoid of an expensive transition-metal catalyst, ligands or toxic carbon monoxide. We executed an I2/DMSO-mediated desirable oxidation of the C(sp3)–H bond of the carbonyl precursor followed by the formation of a 3,3-dicyano-2-arylacrylic acid intermediate. Use of readily available starting materials under mild and operationally simple reaction conditions are the major advantages of this strategy.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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