Synthesis of 1,2‐oxazaheterocycles containing an isoindolone moiety from N‐Hydroxyphthalimide
Identifieur interne : 001091 ( France/Analysis ); précédent : 001090; suivant : 001092Synthesis of 1,2‐oxazaheterocycles containing an isoindolone moiety from N‐Hydroxyphthalimide
Auteurs : Alexander Bartovic [Slovaquie] ; Bernard Decroix [France] ; P. Netchitaïlo [France]Source :
- Journal of Heterocyclic Chemistry [ 0022-152X ] ; 2000-07.
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 CO bond.
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DOI: 10.1002/jhet.5570370426
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<front><div type="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 CO bond.</div>
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