3‐Methyl‐4‐oxa‐5‐azahomoadamantane as an Organocatalyst for the Aerobic Oxidation of Primary Amines to Oximes in Water

Abstract

A simple and efficient catalytic system for the aerobic oxidation of primary amines into corresponding oximes has been developed, with 3‐methyl‐4‐oxa‐5‐azahomoadamantane as catalyst, acetaldoxime as co‐catalyst and water as solvent. This process, which uses oxygen (O2) as an economic and green oxidant and water as a green solvent, tolerates a wide range of substrates, affording the target oximes in moderate to excellent yields. It was found that high selectivity was achieved when 3‐methyl‐4‐oxa‐5‐azahomoadamantane was used, and E‐type oximes were the only detected products. A possible mechanism for this catalytic process is proposed.magnified image

Development of 2-Methoxyhuprine as Novel Lead for Alzheimer’s Disease Therapy

“…Compound (±)- 5 was used to the next reaction without further purification. 1 H- and 13 C-NMR spectra were in good agreement with published data [ 27 , 28 ].…”

“…The synthetic approach for the preparation of (±)-HupY and its 2-methoxy derivative (±)- 1 is depicted in Scheme 1 . The synthesis followed the known two-step protocol [ 27 , 28 ]. The fragmentation reaction of commercially available 1,3-dibromoadamantane ( 2 ) or 1,3-adamantanediol ( 3 ) generated ketone 4 in 82% and 77% yields, respectively.…”

A Synergic Activity of Urea/Butyl Imidazolium Ionic Liquid Supported on UiO-66-NH2 Metal–Organic Framework for Synthesis of Oximes

“…Although various methods have been developed recently for the synthesis of oximes such as decomposition of tosylhydrazones [45], oxidation of methylarenes (in the presence of a nitrogen source) [46], oxidation of primary amines [47], ammoximation of different ketones and aldehydes using polyexometalates [48,49], and transoximation [50], but the conventional method is still considered due to the simplicity of the procedure. Oximes are generally synthesized via a F o r P e e r R e v i e w 3 condensation reaction of carbonyl compounds (aldehydes and ketones) with hydroxylamine in acidic or basic conditions [51].…”

9-Anthraldehyde oxime: a synthetic tool for variable applications

“…Besides the classical preparation method from aldehyde and hydroxylamine, other synthetic approaches can be found in the literature. The preparation of 9-anthraldehyde oxime (2) has been described in two different ways by Yu and coauthors [6,7]. In a first method, 9-methylanthracene (1) was treated with N-hydroxyphthalimide (NHPI) and tert-butyl nitrite (TBN) in acetonitrile as a solvent under nitrogen at 80 °C for 24 h in the presence of Cu(OAc) 2 as the catalyst; the 9-anthraldehyde oxime (2) was obtained in 85% yield (Scheme 1).…”