The regioselectivity of dehydrobenzene reaction with 10-substituted benzo[b][1,6]naphthyridines was found to depend on electronic effects due to the C-10 substituent. Stevens rearrangement of 10-cyano-substituted naphthyridines produced 1-alkyl-2-phenyltetrahydrobenzonaphthyridines. 10-Carbamoyl-substituted naphthyridines underwent Hoffman cleavage of the tetrahydropyridine ring, giving 3-phenylallylaminomethyl-2-vinylquinolines.
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This work received financial support from the Russian Foundation for Basic Research (grants 13-03-90431 Ukrfa, 12-03-31134) and the Grants Council of the President of Russian Federation (grant MK-2367.2013.03).
The authors would like to express their gratitude to the Collective Use Center of Peoples' Friendship University of Russia for the 1Н NMR spectra.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 291-297, February, 2014.
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Varlamov, A.V., Guranova, N.I., Listratova, A.V. et al. Transformations of 10-Substituted Tetrahydrobenzo[b][1,6]naphthyridines through Interaction with Dehydrobenzene. Chem Heterocycl Comp 50, 264–270 (2014). https://doi.org/10.1007/s10593-014-1470-y
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DOI: https://doi.org/10.1007/s10593-014-1470-y