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Protonation of isomeric angular pyrroloquinolines

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Abstract

The protonation (deuteration) rate, KD, for the β-position of the pyrrole ring has been measured for several angular pyrroloquinolines. A relationship has been found between the KD values and the PMR spectral parameters characterizing the structural features of the isomers, enabling the relative reactivities of the latter towards electrophilic substitution reactions to be determined.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1643–1647, December, 1983.

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Kurkovskaya, L.N., Shabunova, V.P., Akhvlediani, R.N. et al. Protonation of isomeric angular pyrroloquinolines. Chem Heterocycl Compd 19, 1298–1302 (1983). https://doi.org/10.1007/BF00842835

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  • DOI: https://doi.org/10.1007/BF00842835

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