Synthesis of thienothiazocinoisoindolediones and thienothiazinoisoindolones from mercaptothiophenes and chloromethylphthalimide
Identifieur interne : 001D73 ( Main/Curation ); précédent : 001D72; suivant : 001D74Synthesis of thienothiazocinoisoindolediones and thienothiazinoisoindolones from mercaptothiophenes and chloromethylphthalimide
Auteurs : Pierre Netchitaïlo [France] ; Mohamed Othman [France] ; Bernard Decroix [France]Source :
- Journal of Heterocyclic Chemistry [ 0022-152X ] ; 1997-01.
Abstract
2‐Thienylthiomethylphthalimides 3a,b were synthesized by action of Chloromethylphthalimide on 2‐or 3‐mercaptothiophene. Reduction of 3a,b and Wittig reaction using carbethoxycarbonyltriphenyl‐phosphorane gave the corresponding acetic acids 5a,b which cyclized under Friedel and Crafts conditions to lead the thienothiazocinoisoindolediones 6a,b. Thienothiazinoisoindolones 7a,b were obtained from hydroxyisoindolones derivatives 4a,b in acid conditions via an acyliminium ion.
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DOI: 10.1002/jhet.5570340150
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<front><div type="abstract">2‐Thienylthiomethylphthalimides 3a,b were synthesized by action of Chloromethylphthalimide on 2‐or 3‐mercaptothiophene. Reduction of 3a,b and Wittig reaction using carbethoxycarbonyltriphenyl‐phosphorane gave the corresponding acetic acids 5a,b which cyclized under Friedel and Crafts conditions to lead the thienothiazocinoisoindolediones 6a,b. Thienothiazinoisoindolones 7a,b were obtained from hydroxyisoindolones derivatives 4a,b in acid conditions via an acyliminium ion.</div>
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