Nitrones and nitronic acid derivatives: An update

Breuer, Eli

doi:10.1002/9780470772195.ch3

Cited by 14 publications

(18 citation statements)

References 221 publications

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“…A great deal of literature is devoted to certain aspects of nitrone chemistry and its application, or to spesific classes of nitrones (34,35) . However, at the present time, the reviews dealing with all or practically all aspects of nitrone chemistry, except those which are well-known and widely covered in the literature (36)(37)(38)(39)(40)(41) , are still lacking.…”

Section: Scheme (1)mentioning

confidence: 99%

Synthesis , Characterization and computional study of Some New Aniline oxide derivatives

Turki

2019

University of Thi-Qar Journal

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Section: Scheme (1)mentioning

confidence: 99%

Synthesis , Characterization and computional study of Some New Aniline oxide derivatives

Turki

2019

University of Thi-Qar Journal

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“…The direct microwave-induced oxidation of primary amines with oxone over silica gel or alumina, [7] the three-step procedure involving cyanomethylation of primary amines, nitrone formation, and hydroxylaminolysis of the nitrones, [8] the asymmetric hydrogenation of nitrones with an iridium catalyst system, [9] the oxidation of primary amines to nitrones followed by hydrolysis under acidic conditions, or treatment with hydroxylamine to afford the desired N-alkylhydroxylamine (this protocol is applicable only to a limited substrates), [10] and finally the alkylation of amines with a-haloacetonitrile followed oxidation to give the convertible nitrone [11] should also be mentioned.…”

Section: Introductionmentioning

confidence: 99%

Oxidation of Primary Amines to N‐Monoalkylhydroxylamines using Sodium Tungstate and Hydrogen Peroxide‐Urea Complex

Heydari

Aslanzadeh

2005

Adv Synth Catal

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Abstract:The sodium tungstate-catalyzed (10 mol %) oxidation of primary amines with a urea-hydrogen peroxide complex (UHP) gives the corresponding N-monoalkylhydroxylamines, which are important biologically active compounds, in good to excellent yields. The method is applicable for a wide range of primary amines, including chiral benzylic amines, a-1,2-hydroxylamine and a-amino esters.Keywords: homogeneous catalysis; hydroxylamines; tungsten; urea-hydrogen peroxide complex a-Hydroxylamino acids and hydroxamic acids have important biological activities. The synthesis of their precursors, N-monoalkylhydroxylamines, has been a topic of considerable research interest.[1] Our investigations have revealed only few examples of the synthesis of Nmonoalkylhydroxylamines from primary amines. These involve the oxidation of the amine with an appropriate oxidation reagent such as benzoyl peroxide (this method requires treatment of an intermediate O-benzylated hydroxylamine with base in order to obtain the free hydroxylamine), [2] hydrogen peroxide or m-chloroperbenzoic acid (this often leads to overoxidation products such as nitroso and nitro compounds and is generally ineffective), [3] or the reduction of the corresponding nitroso and/or nitro compound, or oxime (this method is not applicable to the synthesis of optically active N-alkylhydroxylamines).[4] Other reported methods include the oxidation of a primary amine with dimethyldioxirane (this protocol is applicable to only a limited range of substrates), [5] and the indirect oxidation of primary amines, involving imine formation, oxidation, and oxaziridine hydrolysis [6] (this method is amenable to the synthesis of optically active hydroxylamines, although the acid-labile Schiff base is one of its disadvantages). The direct microwave-induced oxidation of primary amines with oxone over silica gel or alumina, [7] the three-step procedure involving cyanomethylation of primary amines, nitrone formation, and hydroxylaminolysis of the nitrones, [8] the asymmetric hydrogenation of nitrones with an iridium catalyst system, [9] the oxidation of primary amines to nitrones followed by hydrolysis under acidic conditions, or treatment with hydroxylamine to afford the desired N-alkylhydroxylamine (this protocol is applicable only to a limited substrates), [10] and finally the alkylation of amines with a-haloacetonitrile followed oxidation to give the convertible nitrone [11] should also be mentioned.In connection with our interest in one-pot, three-component coupling reactions involving 1,3-asymmetric induction of aldehydes, hydroxylamines and nucleophiles in a 5.0 M solution of lithium perchlorate in diethyl ether, [12] we required access to various optically active N-alkylhydroxylamines. In the course of these studies we encountered difficulties in the oxidation of primary amines to the corresponding hydroxylamines. We investigated a series of reagents for this transformation and discovered that using sodium tungstate (Na 2 WO 4 ) in the presence of the hydrogen peroxide/urea comple...

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“…Nitroxide radicals belong to the most common classes of stable free radicals. Owing to their EPR activity, nitroxides play a crucial role in the investigations of many chemical, especially bio-organically oriented problems 114,115 , and are also involved in various industrial applications 89,106 .…”

Section: Determination Of N-oxo Compoundsmentioning

confidence: 99%

“…The importance of N-oxo compounds is connected with their technological applicability and use as pharmaceuticals (Table 19) and also as reagents in bio-organic (Table 20) and organic chemistry [85][86][87][88][105][106][107][108][109][110][111][112][113][114][115] . In this section, we concentrate on amine N-oxides [86][87][88] , nitroxide radicals and nitrones 89,[106][107][108][109][110][111][112][113][114][115] , and also on nitroso-compounds [116][117][118][119][120][121] .…”

Section: Determination Of N-oxo Compoundsmentioning

confidence: 99%

Trifluoroacetic anhydride-sodium iodide reagent. Nature and applications

Kudzin¹,

Kudzin²,

Drabowicz³

et al. 2007

Arkivoc

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Trifluoroacetic anhydride -sodium iodide mixture (TFAA-NaI; TFAA-I) reacts with several compounds bearing semipolar X-O bond, usually in the mode of deoxygenation, with liberation of iodine. The results of systematic investigations of the TFAA-I-reaction with various types of S-oxo and N-oxo compounds were discussed. The majority of these reactions are characterized by quantitative course, with respect to both X-O substrate transformation as well as to the amounts of liberated iodine. On this basis, a variety of sulphoxides and sulphimides were successfully reduced to sulphides and/or arene-N-oxides to amines, using TFAA-I at ambient temperature. Arene-and alkyl-sulphonic acids were reduced to the corresponding thiol derivatives in moderate yields. Stoichiometric course of the TFAA-I reaction with several S-oxo and N-oxo compounds gave origin to their analytical determinations. Thus, due to stoichiometric amounts of iodine formed from sulphoxides, sulphimides, arene-N-oxides, nitrones and nitroxide radicals, and nitroso compounds -the TFAA-I reagent can be applied to their analytical determination (titrimetric on µmol and spectrometric on nmol scale) and/or TLC detection.

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Nitrones and nitronic acid derivatives: An update

Cited by 14 publications

References 221 publications

Synthesis , Characterization and computional study of Some New Aniline oxide derivatives

Synthesis , Characterization and computional study of Some New Aniline oxide derivatives

Oxidation of Primary Amines to N‐Monoalkylhydroxylamines using Sodium Tungstate and Hydrogen Peroxide‐Urea Complex

Trifluoroacetic anhydride-sodium iodide reagent. Nature and applications

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