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Synthesis of Sulfonyloxindoles via Functional Group Exchange Between 3‐Sulfonylphthalide and Isatylidenemalononitrile
Author(s) -
Satham Lakshminarayana,
Suresh Alati,
Namboothiri Irishi N. N.
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100148
Subject(s) - chemistry , malononitrile , aromatization , conjugate , phthalide , functional group , michael reaction , reactivity (psychology) , sulfonyl , group (periodic table) , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , polymer , medicine , mathematical analysis , alternative medicine , mathematics , alkyl , pathology
An unusual reactivity of 3‐sulfonylphthalides with isatylidenemalononitriles has been exploited to provide an efficient entry into 3‐sulfonyloxindoles. Although a Hauser‐Kraus mechanism can be visualized for the observed transformation, a more probable mechanism, based on control experiments and spectroscopic studies, involves Michael addition of sulfonylphthalide to isatylidenemalononitrile followed by elimination and re‐addition of sulfonyl and malononitrile functionalities in an overall functional group exchange between phthalide and oxindolyl moieties. We have also demonstrated the synthetic applications of the sulfonyloxindoles in selected reactions such as conjugate addition and aromatization.