G. T. Sukhanov, Yu. V. Filippova, Yu. V. Gatilov, A. G. Sukhanova, K. K. Bosov, I. A. Krupnova, E. V. Pivovarova, “Acidic <i>N</i>-dealkylation in nitrotriazolium salts”, Mendeleev Commun., 2022, Volume 32, Issue 2,Pages <nobr>215

This article is cited in 1 paper

Communications

Acidic N-dealkylation in nitrotriazolium salts

G. T. Sukhanov^a, Yu. V. Filippova^a, Yu. V. Gatilov^b, A. G. Sukhanova^a, K. K. Bosov^a, I. A. Krupnova^a, E. V. Pivovarova^a

^a Institute for Problems of Chemical & Energetic Technologies, Siberian Branch of the Russian Academy of Sciences, Biysk, Russian Federation
^b N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russian Federation

Abstract: New selective synthesis of 1-alkyl-5-nitro-1,2,3-triazoles and 1-alkyl-4-nitro-1,2,3-triazoles has been developed, involving acid N-dealkylation of the relative 4-nitro-1,2,3- and 3-nitro- 5-R-1,2,4-triazolium salts. The assortment of novel 1-alkyl- 4(5)-nitro-1,2,3-triazoles has been thus essentially expanded. Treatment of relative 3-nitro-1,2,4-triazolium salts with HCl or HBr proceeds mostly as S_N^ipso-substitution of the nitro group.

Keywords: 1,2,3-triazolium salts, 1,2,4-triazolium salts, nitrotriazoles, alkyltriazoles, dealkylation, S_N^ipso-substitution, regioselectivity.

Language: English

DOI: 10.1016/j.mencom.2022.03.020

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