Sustainable electrochemical synthesis of aliphatic nitro-NNO-azoxy compounds employing ammonium dinitramide and their in vitro evaluation as potential nitric oxide donors and fungicides
Alexander S Budnikov, Nikita E Leonov, Michael S Klenov, Andrey A Kulikov, Igor B Krylov, Timofey A Kudryashev, Aleksandr M Churakov, Alexander O Terent’ev, Vladimir A Tartakovsky
TL;DR
A sustainable electrochemical method was developed to synthesize aliphatic nitro-NNO-azoxy compounds using ammonium dinitramide, which also showed potential as nitric oxide donors and fungicides.
Contribution
A green electrochemical synthesis method using ammonium dinitramide as both oxidant and reagent is introduced.
Findings
The method allows for atom- and step-economical synthesis of aliphatic nitro-NNO-azoxy compounds.
The synthesized compounds exhibit significant nitric oxide donor activity and fungicidal properties.
The process is scalable and practical, using constant current electrolysis in an undivided cell.
Abstract
An atom- and step-economical electrochemical method for the synthesis of aliphatic nitro-NNO-azoxy compounds from the corresponding nitroso compounds was developed employing ammonium dinitramide, a prospective green oxidant for aerospace propulsion applications, as both electrolyte and source of a =NNO2 group. The developed method is green, practical, and scalable due to constant current electrolysis in an undivided cell at high current densities. Synthesized products demonstrated pronounced NO-donor activity and fungicidal activity against phytopathogenic fungi.
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Taxonomy
TopicsEnergetic Materials and Combustion · Oxidative Organic Chemistry Reactions · Advanced battery technologies research