E. A. Sheremet, R. I. Tomanov, E. V. Trukhin
Apr 1, 2004
Citations
1
Influential Citations
64
Citations
Journal
Russian Journal of Organic Chemistry
Abstract
It is known that some 1,2,3-triazole derivatives possess practically important properties. For example, 4-(4-methoxyphenyl)-5-nitro-1,2,3-triazole exhibits antifungal activity, and 4-(4-bromophenyl)and 4-(4nitrophenyl)-5-nitro-1,2,3-triazoles are tuberculostatic and fungicide agents [1]. Some 1,2,3-triazoles can be used as photostabilizers and optical bleaching agents [2, 3], and they may be regarded as precursors of azapurines which are potential carcinostatic agents [2]. The synthesis of nitro-1,2,3-triazoles having aryl substituents at the ring carbon atoms was described by Khisamutdinov and co-workers [1, 4]. It is based on the reaction of 2-aryl-1-bromo-1-nitroethenes or 2-aryl-1,2-dibromo-2-nitroethanes with sodium azide in aprotic (DMF, DMSO) or protic (ethanol) solvents. 1,1-Dinitroethene derivatives, specifically β,β-dinitrostyrenes, are highly reactive compounds [5–8] which can be used in the synthesis of nitro-1,2,3triazoles. We have shown that β,β-dinitrostyrenes I–III react with 2 equiv of sodium azide under fairly mild conditions, in anhydrous acetonitrile at room temperature. The reaction takes 2.5–4.5 h, and the products are 4-aryl-5-nitro-1,2,3-triazoles VII–IX which are formed in 59–77% yield. Compounds VII–IX were also synthesized by independent method from the corresponding β-bromo-β-nitrostyrenes and sodium azide in DMF, following a slightly modified procedure