One-Pot Construction of Functionalized Spiro-dihydronaphthoquinone-oxindoles via Hauser–Kraus Annulation of Sulfonylphthalide with 3‑Alkylideneoxindoles

One-Pot Construction of Functionalized Spiro-dihydronaphthoquinone-oxindoles via Hauser–Kraus Annulation of Sulfonylphthalide with 3‑Alkylideneoxindoles

The Hauser–Kraus annulation of sulfonylphthalide with 3-olefinic oxindole has been performed. This strategy, which involves a cascade Michael addition–Dieckmann cyclization–elimination sequence, offers rapid and convenient access to novel spiro-dihydronaphthoquinone-oxindoles in excellent yields wit...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-12, Vol.82 (23), p.12939-12944
Main Authors: Sivasankara, Chenikkayala, Satham, Lakshminarayana, Namboothiri, Irishi N. N
Format: Article
Language:eng
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Summary:The Hauser–Kraus annulation of sulfonylphthalide with 3-olefinic oxindole has been performed. This strategy, which involves a cascade Michael addition–Dieckmann cyclization–elimination sequence, offers rapid and convenient access to novel spiro-dihydronaphthoquinone-oxindoles in excellent yields with complete selectivity for the enolic form under mild reaction conditions.
ISSN:0022-3263
1520-6904