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

Elisabetta MassoloMargherita PirolaAlessandra PuglisiSergio RossiMaurizio Benaglia
Published in: RSC advances (2020)
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 γ-butyrolactone, the desired N -aryl butanamide derivative was obtained, featuring a chlorine atom at the γ-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.
Keyphrases
  • randomized controlled trial
  • molecular dynamics
  • electron transfer
  • high resolution
  • simultaneous determination
  • water soluble