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

Authors

  • А. В. Варламов Peoples Friendship University of Russia
  • Н. И. Гуранова Peoples Friendship University of Russia
  • А. В. Листратова Peoples Friendship University of Russia
  • Т. Н. Борисова Peoples Friendship University of Russia
  • В. Н. Хрусталёв A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences
  • А. А. Титов Peoples Friendship University of Russia
  • Л. Г. Воскресенский Peoples Friendship University of Russia

DOI:

https://doi.org/10.1007/1492

Keywords:

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

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

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Published

2014-02-28

Issue

No. 2 (2014)

Section

Original Papers