Abstract
The mononitration of benz[e]-, benz[f]-, and benz[g]isatins and their tetrahydro derivatives was realized. It was established on the basis of an analysis of the 1H NMR and mass spectra that substitution takes place at position 5 in the derivatives of the [g] series and at the position adjacent to the NH group in derivatives of the [f] series and in the case of 6,7,8,9-tetrahydrobenz [e]isatin. This reaction path corresponds to the maximum electron density in the HOMO, calculated by the CNDO method. In benz[e]isatin, contrary to the general relationship and to the quantum-chemical prediction, the nitro group initially enters the ring annellated with the indole ring.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 60–65, January, 1989.
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Mazhilis, L.I., Terent'ev, P.B. & Bolotin, V.A. Mononitration of derivatives of benzisatins. Chem Heterocycl Compd 25, 50–55 (1989). https://doi.org/10.1007/BF00472618
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DOI: https://doi.org/10.1007/BF00472618