FUNCTIONALIZED DERIVATIVES OF 2-METHYL-5-NITRO-1,2,4-TRIAZOL-3-ONE
VJSBLH
DOI:
https://doi.org/10.25712/ASTU.2072-8921.2024.04.028Abstract
The interest in five-membered heterocyclic compounds of the 1,2,4-triazole series arises from the presence of several reaction sites in the molecule of the starting triazole synthon, allowing these structures to be considered as an effective building block in the synthesis of new derivatives from them, on one hand. On the other hand, systematic studies have revealed a wide range of practically useful and unique properties of the said class of compounds, making them quite valuable objects for use in various science and technology fields. Therefore, the research towards designing new 1,2,4-triazole derivatives and investigating their reactivity and properties is very relevant and promising. The present study synthesized never-before-seen 2-methyl-5-nitro-1,2,4-triazol-3-one derivatives structurally bearing various reactive functional groups such as the propargyl, cyanomethyl and allyl. The creation of functionalized triazolone derivatives relies on the alkylation reaction of the activated salt form of 2-methyl-5-nitro-1,2,4-triazol-3-one synthon with different types of alkylating agent (propargyl bromide, chloroacetonitrile, allyl bromide) in a polar aprotonic solvent over an organic catalyst. The structure of the obtained series of new functionalized derivatives of 2-methyl-5-nitro-1,2,4-triazol-3-one was reliably validated by comprehensive characterization using spectral analytical techniques (1H, 13C NMR and IR spectroscopy). The thermal behavior of the target products was studied by DSC and TGA methods. Incorporating new, sufficiently reactive sites of different nature into the basic structure of 2-methyl-5-nitro-1,2,4-triazol-3-one can modify the physicochemical characteristics and expand the synthetic potential of the derived compounds, and makes them attractive substrates for organic synthesis to design new, potentially bioactive molecules.
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Copyright (c) 2024 Konstantin K. Bosov, Irina A. Krupnova, Ekaterina V. Pivovarova, Gennady T. Sukhanov, Anna G. Sukhanova, Yulia V. Filippova
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