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The features of nucleophilic substitution of the nitro group in 4-alkyl-6-nitro-1,2,4-triazolo[5,1-c][1,2,4]triazines

E. N. Ulomsky, D. N. Lyapustin, V. V. Fedotov, O. S. El'tsov, I. M. Sapozhnikova, D. N. Kozhevnikov, E. M. Mukhin

Abstract


The nucleophilic substitution of the nitro group of 4-alkyl-6-nitro-4,7-dihydro-1,2,4-triazolo[5,1-c][1,2,4]triazine-7-ones on the example of interactionwith morpholine was studied. It is established that under the action of excess cycloalkylimine at room temperature the unusual easy disclosure of triazine cycle with the formation of sterically hindered hydrazones occurs which are the key intermediates for further transformations. The carrying of reaction at elevated temperatures leads to the formation of products of substitution of the nitro group with the amine and also with morpholyl hydrazones which are the products of hydrolysis of amides of hydrazones and subsequent decarboxylation. Thus, the nucleophilic substitution of the nitro group in the described triazolotriazines flows through the ANRORC mechanism.

Keywords


nucleophilic substitution; ANRORC; the transformation of 4-alkyl-6-nitro-1,2,4- triazolo[5,1-c][1,2,4]triazine-7-ones; morpholine

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References


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DOI: https://doi.org/10.15826/chimtech.2017.4.1.020

Copyright (c) 2017 E. N. Ulomsky, D. N. Lyapustin, V. V. Fedotov, O. S. Eltsov, I. M. Sapozhnikova, D. N. Kozhevnikov, E. M. Mukhin

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