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Heterocyclic nitro compounds

I. Synthesis of nitro derivatives of 1, 2, 4-triazole, 1, 3, 4-thiadiazole, tetrazole, 1, 3, 4-oxadiazole, and pyrazole by the noncatalytic replacement of the diazo group by the nitro group

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Replacement of the diazo group by the nitro group has given nitro derivatives of 1, 2, 4-triazole, 1, 3, 4-thiadiazole, tetrazole, 1, 3, 4-oxadiazole, and pyrazole. The reaction is a nucleophilic substitution, proceeding by a heterolytic mechanism. A similar reaction does not occur with 2-amino pyridine and 2-amino imidazole, possibly as a result of the low stability of the diazonium form of the corresponding diazo compounds.

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Bagal, L.I., Pevzner, M.S., Frolov, A.N. et al. Heterocyclic nitro compounds. Chem Heterocycl Compd 6, 240–244 (1970). https://doi.org/10.1007/BF00475005

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