22860-01-1Relevant articles and documents
Self-catalyzed direct amidation of ketones: A sustainable procedure for acetaminophen synthesis
Rancan, Elia,Aricò, Fabio,Quartarone, Giuseppe,Ronchin, Lucio,Tundo, Pietro,Vavasori, Andrea
, p. 11 - 16 (2014)
High yielding amination of ketones and benzaldehyde in acid-less conditions has been conducted on several ketones to achieve amides and nitriles. The reactivity of the selected substrates showed to depend on both oximation and Beckmann rearrangement reaction rates. Oximation allows the in-situ production of hydrochloric acid that enables Beckmann rearrangement of the oxime to form the corresponding amide or nitrile. It is noteworthy that, using this one-pot synthetic approach, N-acetyl-4-aminophenol (acetaminophen drug), can be easily synthesized starting from 4-hydroxy-acetophenone in high yield. Acetanilide and ε-caprolactam can be also efficiently synthesized employing this synthetic procedure.
O-TBS-N-tosylhydroxylamine: A reagent for facile conversion of alcohols to oximes
Kitahara, Katsushi,Toma, Tatsuya,Shimokawa, Jun,Fukuyama, Tohru
supporting information; experimental part, p. 2259 - 2261 (2009/05/26)
(Chemical Equation Presented) A variety of oximes were synthesized from the corresponding alcohols, alkyl halides, or alkyl sulfonates without using external oxidants. With this simple two-step procedure involving substitution with readily available TsNHOTBS and subsequent treatment with CsF, a range of oximes were prepared including the ones hardly preparable with conventional procedures.