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

E. Massolo;M. Pirola;A. Puglisi;S. Rossi;M. Benaglia
2020

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
gen-2020
Article (author)
File in questo prodotto:
File Dimensione Formato  
RSC Advances.pdf

accesso aperto

Tipologia: Publisher's version/PDF
Dimensione 532.11 kB
Formato Adobe PDF
532.11 kB Adobe PDF Visualizza/Apri
Pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/707990
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 14
  • ???jsp.display-item.citation.isi??? 14
social impact