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Synthesis of 1,2-oxazaheterocycles containing an isoindolone moiety from N-Hydroxyphthalimide

✍ Scribed by Alexander Bartovic; Bernard Decroix; P. Netchitaïlo

Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
276 KB
Volume
37
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Syntheses of the isoindolobenzoxazinone 1a and thienoxazinoisoindolones 1b,c was developed from N‐hydroxyphthalimide 3 and halogenomethylaryl derivatives. The resulting aryloxy phthalimides 4a‐c were reduced to hydroxylactams 5a‐c which cyclized in acidic conditions. A Wittig reaction on 5a using carbethoxymethylidenetriphenylphosphorane gave the corresponding acid 6 which treated in Friedel and Crafts conditions led to the isoxazolinone 8 by cleavage of the benzyl CO bond.

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