Abstract: Interaction of polyfluorinated chalcones (pentafluorobenzalacetophenone, benzalpentafluoroacetophenone and decafluorochalcone) with 1,2-diaminobenzene in alcohols in the presence of triethylamine or quaternary ammonium salt (TEBAC) has been investigated. In the presence of TEBAC in 2-propanol polyfluorinated 2,4-diaryl-2,3-dihydro-1H-1,5-benzodiazepines are formed. Some of them undergo intramolecular fluorine substitution and unusual rearrangement into a previously unknown polyfluoro-containing tetracyclic compounds-(6aR)-1,2,3,4-tetrafluoro-6a-aryl-6a,7-dihydrobenzimidazo[1,2-a]quinolines, under the reaction conditions as well as in absence of TEBAC. The structures are established on NMR spectra and confirmed by X-ray. (C) 2014 Elsevier B.V. All rights reserved.

Cite: Borodina E.A. , Orlova N.A. , Kargapolova I.Y. , Gatilov Y.V.
Polyfluorinated 2,4-diaryl-2,3-dihydro-1H-1,5-benzodiazepines: Synthesis and new rearrangement into polyfluorodihydrobenzimidazo[1,2-a]quinolines
Journal of Fluorine Chemistry. 2014. V.162. P.66-70. DOI: 10.1016/j.jfluchem.2014.03.013 WOS Scopus РИНЦ

Dates:

Published print:

Jun 1, 2014

Identifiers:

Web of science	WOS:000336827000009
Scopus	2-s2.0-84899538076
Elibrary	21874107
OpenAlex	W2062305257

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