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A one-pot route to N-acyl ureas: a formal four-component hydrolytic reaction involving aminonitrones and isocyanide dibromides

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Abstract

One-pot interplay between aminonitrones, isocyanides, dibromine, and water proceeds to give N-acyl ureas. This formally four-component reaction occurs via the initial generation of electrophilically activated 1,2,4-oxadiazolium salts, which then hydrolyze to grant N-acyl ureas. XRD structural and theoretical DFT studies indicated that the quasi-cyclic conformation of the N-acyl ureas is caused by moderate strength (6.2–7.8 kcal mol−1) intramolecular resonance-assisted hydrogen bonding, while their solid-state dimerization is determined by the collective action of intermolecular N–H⋯O (4.1–7.5 kcal mol−1) and C–H⋯O (1.6–4.7 kcal mol−1) hydrogen bonding. The results of the kinetic study accompanied by DFT calculations show that the generated 2-substituted 1,2,4-oxadiazolium salts are, as expected, significantly more reactive toward nucleophilic addition than the corresponding 1,2,4-oxadiazoles.

Graphical abstract: A one-pot route to N-acyl ureas: a formal four-component hydrolytic reaction involving aminonitrones and isocyanide dibromides

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Article information


Submitted
31 Oct 2019
Accepted
15 Dec 2019
First published
16 Dec 2019

New J. Chem., 2020, Advance Article
Article type
Paper

A one-pot route to N-acyl ureas: a formal four-component hydrolytic reaction involving aminonitrones and isocyanide dibromides

M. V. Il’in, L. A. Lesnikova, D. S. Bolotin, A. S. Novikov, V. V. Suslonov and V. Yu. Kukushkin, New J. Chem., 2020, Advance Article , DOI: 10.1039/C9NJ05445F

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