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.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 345–352, February, 2011.
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Ukhin, L.Y., Shepelenko, E.N., Belousova, L.V. et al. 2-Aminothiophene derivatives in a novel synthesis of phthalimidines. Russ Chem Bull 60, 352–360 (2011). https://doi.org/10.1007/s11172-011-0057-3
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DOI: https://doi.org/10.1007/s11172-011-0057-3