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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R. É. Valter, Ring-Chain Isomerism in Organic Chemistry [in Russian], Zinatne, Riga (1978), p. 238.
E. Regel and K.-H. Büchel, Ann., No. 1, 145 (1977).
R. É. Valter and S. P. Valter, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 6, 704 (1969).
W. Flitsch, Chem. Ber.,103, 3205 (1970).
L. A. M. Bastiaansen and E. F. Godefroi, Synthesis, No. 9, 675 (1978).
A. R. Katritzky and A. P. Ambler, in: Physical Methods in the Chemistry of Heterocyclic Compounds, Academic Press (1963).
R. É. Valter and G. A. Karlivan, Khim. Geterotsikl. Soedin., No. 9, 1207 (1976).
R. É. Valter and G. A. Karlivan, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 1, 61 (1976).
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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/PL00020564
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DOI: https://doi.org/10.1007/PL00020564