Jump to main content
Jump to site search

Issue 8, 2013
Previous Article Next Article

The reaction of NH-indazoles with 1-fluoro-2,4-dinitrobenzene: the unusual formation of benzotriazole-N-oxides

Author affiliations

Abstract

When N-unsubstituted indazoles, like indazole itself, reacted with 1-fluoro-2,4-dinitrobenzene or 1-chloro-2,4,6-trinitrobenzene, three products were obtained whose structures were determined by X-ray diffraction. Besides the two N-substituted nitroaryl derivatives, a third compound was obtained with the same molecular formula (C13H8N4O4) to which was assigned the structure of a derivative of benzotriazole N-oxide. With the combined use of crystallography, NMR and DFT calculations this reaction was studied with special stress on the mechanism of formation of the benzotriazole-N-oxide.

Graphical abstract: The reaction of NH-indazoles with 1-fluoro-2,4-dinitrobenzene: the unusual formation of benzotriazole-N-oxides

Back to tab navigation

Supplementary files

Publication details

The article was received on 18 Feb 2013, accepted on 30 Apr 2013 and first published on 01 May 2013


Article type: Paper
DOI: 10.1039/C3NJ00186E
Citation: New J. Chem., 2013,37, 2384-2398
  •   Request permissions

    The reaction of NH-indazoles with 1-fluoro-2,4-dinitrobenzene: the unusual formation of benzotriazole-N-oxides

    I. Alkorta, F. P. Cossío, J. Elguero, N. Fresno, L. Hernandez-Folgado, S. García-Granda, L. Menéndez-Taboada, R. Pérez-Fernández, F. Reviriego and L. Vázquez-Viñuela, New J. Chem., 2013, 37, 2384
    DOI: 10.1039/C3NJ00186E

Search articles by author

Spotlight

Advertisements