Transformations of 10-substituted tetrahydro-benzo[b][1,6]naphthyridines through interaction with dehydrobenzene

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 © 2014 Springer Science+Business Media New York 119.

Authors
Varlamov A.V. 1 , Guranova N.I. 1 , Listratova A.V. 1 , Borisova T.N. 1 , Khrustalev V.N. 2 , Titov A.A. 1 , Voskressensky L.G. 1
Journal
Chemistry of Heterocyclic Compounds
Publisher
Латвийский институт органического синтеза Латвийской академии наук / Springer New York Consultants Bureau
Number of issue
2
Language
English
Pages
264-270
Status
Published
Link
External link
DOI
10.1007/s10593-014-1470-y
Volume
50
Year
2014
Organizations
  • 1 Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation
  • 2 A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow 119991, Russian Federation
Keywords
2-vinylquinolines; Dehydrobenzene; Domino reaction; Stevens rearrangement; Tetrahydrobenzo[b][1.6]naphthyridines
Date of creation
19.10.2018
Date of change
19.10.2018
Short link
https://repository.rudn.ru/en/records/article/record/5040/
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