A two-step one pot, experimentally simple protocol, based on readily available and inexpensive reagents allowed the conversion of nitro-arenes directly to N-aryl amides. A metal-free reduction of the nitro group, mediated by trichlorosilane, followed by the addition of an anhydride afforded the corresponding N-aryl carboxyamide, that was isolated after a simple aqueous work up in good-excellent yields. When the methodology was applied to the reaction with g-butyrolactone, the desired N-aryl butanamide derivative was obtained, featuring a chlorine atom at the g-position, a functionalized handle that can be used for further synthetic manipulation of the reaction product. Such an intermediate has already been employed as a key advanced precursor of pharmaceutically active compounds.
A one pot protocol to convert nitro-arenes into N-aryl amides / E. Massolo, M. Pirola, A. Puglisi, S. Rossi, M. Benaglia. - In: RSC ADVANCES. - ISSN 2046-2069. - 10:7(2020 Jan), pp. 4040-4044.
|Titolo:||A one pot protocol to convert nitro-arenes into N-aryl amides|
BENAGLIA, MAURIZIO (Corresponding)
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||gen-2020|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1039/c9ra10758d|
|Appare nelle tipologie:||01 - Articolo su periodico|