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. [10.1039/c9ra10758d]

A one pot protocol to convert nitro-arenes into N-aryl amides

Elisabetta Massolo;Margherita Pirola;Alessandra Puglisi;Sergio Rossi;Maurizio Benaglia
2020-01

Abstract

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.
Settore CHIM/06 - Chimica Organica
RSC ADVANCES
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/707990
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