2-Aminothiophene derivatives in a novel synthesis of phthalimidines View Full Text


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Article Info

DATE

2011-02

AUTHORS

L. Yu. Ukhin, E. N. Shepelenko, L. V. Belousova, Zh. I. Orlova, G. S. Borodkin, K. Yu. Suponitsky

ABSTRACT

New aminophthalides were synthesized from o-formylbenzoic acid and substituted 2-aminothiophenes. Two of these compounds underwent recyclization in boiling Ac2O to give the previously unknown 3-acetoxy-2-(3-cyano-4,5-dimethylthiophen-2-yl)-1,3-dihydroisoindol-1-one and 3-acetoxy-2-(3-cyano-4,5-tetramethylenethiophen-2-yl)-1,3-dihydroisoindol-1-one. The possible reaction mechanism and factors preventing the recyclization, in particular, the formation of intramolecular hydrogen bonds in the starting phthalides, were discussed. Some reactions of the resulting compounds with C-nucleophiles in trifluoroacetic acid were investigated. Two derivatives containing 4-hydroxy-3,5-di-tert-butylphenyl substituents were studied by X-ray diffraction. More... »

PAGES

352

References to SciGraph publications

  • 1975-11. Ring - chain transformations with participation of the C = N group in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
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    http://scigraph.springernature.com/pub.10.1007/s11172-011-0057-3

    DOI

    http://dx.doi.org/10.1007/s11172-011-0057-3

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