Unexpected cyclization of ortho-nitrochalcones into 2-alkylideneindolin-3-ones |
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Authors: | Nicolai A. Aksenov Dmitrii A. Aksenov Nikolai A. Arutiunov Daria S. Aksenova Alexander V. Aksenov Michael Rubin |
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Affiliation: | Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355009 Russian Federation ; Department of Chemistry, University of Kansas, 1567 Irving Hill Rd., Lawrence KS 66045-7582 USA, +1-785-864-5071 |
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Abstract: | An original, facile, and highly efficient method for the preparation of 2-(3-oxoindolin-2-ylidene)acetonitriles from ortho-nitrochalcones is described. The featured transformation is a triggered Michael addition of the cyanide anion to the chalcone followed by a cascade cyclization mechanistically related to the Baeyer–Drewson reaction.Highly efficient cascade involving Michael addition and Baeyer–Drewson reaction is triggered by cyanide anion and transforms ortho-nitrochalcones into 2-(3-oxoindolin-2-ylidene)acetonitriles. |
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