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Alkylation and annulation of 3-(phenylsulfonyl)-2-alkyl-2,3-dihydroisoindol-1-ones

✍ Scribed by Frederick A. Luzzio; DeAnna Piatt Zacherl

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 294 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)00293-7

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✦ Synopsis

The hydroxylactams obtained from reduction of N-substituted phtbalimides were phenylthiated and oxidized to give 3-(phenylsulfonyl)-2$diiydroisoindol-l-ones.

Deprotonation of the sulfones with sodium hydride followed by treatment with electrophiles gave substitution. Sulfones with suitably-disposed a$-unsaturated ester groups gave cyclic products from intramolecular Michael addition. Desulfurixation of the pbenylsulfonyl intermediates was effected in quantitative yield using Raney nickel promoted by ultrasound.

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