Collect. Czech. Chem. Commun. 2009, 74, 811-833
Published online 2009-04-22 11:51:24

Intramolecular base-catalyzed reactions involving interaction between benzene nitro groups and ortho carbon chains

Jiří Hanusek* and Vladimír Macháček

Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic


The review is focused on the understanding of processes involving chemical interaction between benzene nitro group and ortho carbon chain containing heteroatom (N, O, S) adjacent to the ring. In most cases these compounds undergo base-catalyzed cyclization to give heteroaromatic N-oxides that can be subsequently transformed to related heterocycles under the same conditions. However, in some cases, depending on substitution of the benzene ring, side chain or the base used, the formation of other compounds – both heterocyclic and non-heterocyclic such as nitroso and azoxy compounds, spiro Meisenheimer adducts – is observed. Review with 31 references.

Keywords: Cyclization involving nitro group; o-Nitroanilines; o-Nitrophenyl sulfides; o-Nitrophenyl ethers; Benzimidazole N-oxides; Benzothiazole N-oxides; Benzimidazol-2(3H)-ones; 1-Hydroxyquinoxaline-2,3(1H,4H)-diones; Azoxy compounds.

References: 98 live references.