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TRANSFORMATIONS OF 10-SUBSTITUTED TETRAHYDROBENZO[b][1,6]NAPHTHYRIDINES THROUGH INTERACTION WITH DEHYDROBENZENE

А. В. Варламов, Н. И. Гуранова, А. В. Листратова, Т. Н. Борисова, В. Н. Хрусталёв, А. А. Титов, Л. Г. Воскресенский
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Abstract


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‑cyanosubstituted naphthyridines produced 1-alkyl-2-phenyltetrahydrobenzonaphthyridines. 10-Carbamoylsubstituted naphthyridines underwent Hoffman cleavage of the tetrahydropyridine ring, giving 2‑vinyl-3-phenylallylaminomethylquinolines.

How to Cite
Varlamov, A. V.; Guranova, N. I.; Listratova, A. V.; Borisova, T. N.; Khrustalev, V. N.; Titov, A. A.; Voskressensky, L. G. Chem. Heterocycl. Compd. 2014, 50, 264. [Khim. Geterotsikl. Soedin. 2014, 291.]

For this article in the English edition see DOI 10.1007/s10593-014-1470-y


Keywords


imidazo[1,5-a]quinoxalin-4-ones; electron impact ionization; electrospray ionization; mass spectrometry; matrix-assisted laser desorption ionization

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