Abstract: 5,6,7,8-Tetrafluoroquinoxaline (1) and its previously unknown derivatives (2-8) were synthesized from glyoxal and polyfluorinated 1,2-diaminoarenes (10-17) obtained by reduction of corresponding 2,1,3-arenothiadiazoles (including new ones 21 and 22). The thiadiazoles were prepared from polyfluorinated Ar-NH2 via Ar-N=S=N-SiMe3 (34-37) and their fluoride-induced nucleophilic ortho-cyclization. New approaches to Ar-N=S=N-SiMe3 based on interaction between polyfluorinated Ar-N=SCl2 (32) and LiN(SiMe3)(2), and between ArN(SiMe3)Li and Me2Si-N=S=O, were tried together with our previous synthetic method based on reaction of Ar-N=S=O with Me3SnLiN(SiMe3)(2). New polyfluorinated 2,1,3-arenoselenadiazoles (26-28) were prepared from corresponding diamines and SeO2 and 26 also from the diamine and SeCl4. Compounds synthesized were characterized by multinuclear NMR (particularly H-1, F-19, Se-77), compounds 1, 2, 4, 7, 8, 16 (salt with 2 HCl), 19, 26, 28 and 32 by single-crystal X-ray diffraction, and quinoxalines 1-8, thiadiazole 22 and selenadiazoles 27 and 28 by UV-vis and fluorescence techniques. (C) 2014 Elsevier B.V. All rights reserved.

Cite: Makarov A.G. , Selikhova N.Y. , Makarov A.Y. , Malkov V.S. , Bagryanskaya I.Y. , Gatilov Y.V. , Knyazev A.S. , Slizhov Y.G. , Zibarev A.V.
New fluorinated 1,2-diaminoarenes, quinoxalines, 2,1,3-arenothia(selena)diazoles and related compounds
Journal of Fluorine Chemistry. 2014. V.165. P.123-131. DOI: 10.1016/j.jfluchem.2014.06.019 WOS Scopus РИНЦ

Dates:

Published print:

Sep 1, 2014

Identifiers:

Web of science	WOS:000341347800019
Scopus	2-s2.0-84905439909
Elibrary	23977048
OpenAlex	W2023653348

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