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 |
Autori: | BENAGLIA, MAURIZIO (Corresponding) |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
Data di pubblicazione: | gen-2020 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1039/c9ra10758d |
Appare nelle tipologie: | 01 - Articolo su periodico |
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