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

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

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 ca...

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Veröffentlicht in:Journal of heterocyclic chemistry 2000-07, Vol.37 (4), p.827-830
Hauptverfasser: Bartovic, Alexander, Decroix, Bernard, Netchitaïlo, P.
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container_title Journal of heterocyclic chemistry
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creator Bartovic, Alexander
Decroix, Bernard
Netchitaïlo, P.
description 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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title Synthesis of 1,2-oxazaheterocycles containing an isoindolone moiety from N-Hydroxyphthalimide
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