SYNTHESIS OF 2-NITRO-1,3-BIS(3,3’-DIHYDROXYMETHYL)- -1,2,3-TRIAZOLYL-2-AZAPROPANE BY THE REACTION OF AZIDE-ALKYN CYCLOADDITION

Е.О. Shestakova, I.A. Shchurova, S.G. Il’yasov
DOI: 10.25699/SSSB.2021.40.6.002 Download PDF
Abstract: 2-Nitro-1,3-bis (3,3'-dihydroxymethyl)-1,2,3-triazolyl-2-azapropane (2-NDTAP) is of interest as a starting material in the synthesis of high-energy compounds. The article discusses the synthesis of 2-NDTAP the reaction of azide-alkyne cycloaddition 1,3-diazido-2-nitro-2-azapropane with propargyl alcohol in tert-butyl alcohol in the presence of a copper catalyst (wire, copper powder, copper oxide, nano copper oxide). The influence of the catalyst and the temperature of the process on its duration, yield and product quality has been investigated. The structure of 2-NDTAP was confirmed by IR and NMR spectroscopy. As a result, a method for obtaining 2-NDTAP with a yield of 62 % and a basic substance content of more than 97 % was developed.
Index terms: reaction of azide-alkyne cycloaddition, azidoalkylnitramines, 1,3-diazido-2-nitro-2-azapropane, propargyl alcohol, 2-nitro-1,3-bis (3,3'-dihydroxymethyl)-1,2,3-triazolyl-2-azapropane.

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