β-nitro ketones represent highly significant compounds for theirsimultaneous nucleophilic and electrophilic reactive sites in 1,3-related positions. These molecules are commonly obtained vianitration of enones in aprotic apolar organic solvents (suchas THF and CPME) with large excesses of nitrating agentsand acetic acid. In this work the use of weakly acidic naturaldeep eutectic solvents (NADESs) – glycolic acid based-ones –is proposed as both green and catalytic reaction media forthe nitration of enones giving β-nitro ketones. The NADESsmixtures employed were the ones formed by mixing glycolicacid with trimethylglycine, with choline chloride and with water.The reaction proceeded with stochiometric amounts of nitrationagents and taking advantage from the catalytic behavior of theNADESs solvents; the scope was explored giving satisfactoryyields.

Glycolic Acid-Based Natural Deep Eutectic Solvents (NADESs) as Catalytic Reaction Media fo the Synthesis of beta-Nitro Ketones

Dario Gentili;Enrico Marcantoni;Gabriele Lupidi;Matteo Tiecco
2025-01-01

Abstract

β-nitro ketones represent highly significant compounds for theirsimultaneous nucleophilic and electrophilic reactive sites in 1,3-related positions. These molecules are commonly obtained vianitration of enones in aprotic apolar organic solvents (suchas THF and CPME) with large excesses of nitrating agentsand acetic acid. In this work the use of weakly acidic naturaldeep eutectic solvents (NADESs) – glycolic acid based-ones –is proposed as both green and catalytic reaction media forthe nitration of enones giving β-nitro ketones. The NADESsmixtures employed were the ones formed by mixing glycolicacid with trimethylglycine, with choline chloride and with water.The reaction proceeded with stochiometric amounts of nitrationagents and taking advantage from the catalytic behavior of theNADESs solvents; the scope was explored giving satisfactoryyields.
2025
262
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11581/501884
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