Abstract
It was established by IR, UV, and PMR spectroscopy that N-unsubstituted and N-(n-alkyl, sec-alkyl, or aryl)-2-(2-imidazolylcarbonyl)benzamides obtained from imidazo[1,2-b]isoquinoline-5,10-dione and ammonia or amines have the 3-hydroxy-3-(2-imidazolyl)isoindolinone chain structure in the crystalline state and in solutions in dimethyl sulfoxide. The N-(tert-alkyl)amides exist in the open form under these conditions. Protonation of the imidazole nitrogen atom in the N-(tert-butyl)amide molecule leads to its cyclization to 3-hydroxyisoindolinone.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 335–339, March, 1980.
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Karlivan, G.A., Valter, R.É. Ring-chain isomerism of 3-hydroxy-3-(2-imidazolyl)isoindolinones. Chem Heterocycl Compd 16, 247–251 (1980). https://doi.org/10.1007/BF02401720
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DOI: https://doi.org/10.1007/BF02401720