Synthesis of alkyl nitrones by reaction of aldehyde and ketone oximes with α,β-unstaturated esters in the presence of Lewis acid

Koçak, Ahmet; Malkondu, Sait; Kurbanli, Sultan

doi:10.1134/s1070428009040204

Cited by 6 publications

(6 citation statements)

References 15 publications

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“…Nucleophilic addition of oximes by the N atom to a CC bond results in the formation of acyclic nitrones. A series of the aromatic and vinylic aldoximes and ketoximes R 1 R 2 CNOH ( 105 ) reacted with the acrylic acid esters H 2 CC(R 3 )CO 2 R 4 ( 106 ) in the presence of a stoichiometric amount of the CdI 2 /BF 3 · n Bu 2 O system …”

Section: Metal-mediated Reactions Of the Oxime Groupmentioning

confidence: 96%

“…A series of the aromatic and vinylic aldoximes and ketoximes R 1 R 2 CNOH (105) reacted with the acrylic acid esters H 2 CC(R 3 )CO 2 R 4 (106) in the presence of a stoichiometric amount of the CdI 2 /BF 3 • n Bu 2 O system. 274 The reaction proceeded in a variety of solvents such as CH 2 Cl 2 , benzene, and DMF and at a broad range of temperatures (RT−153 °C) for 6−24 h, leading to nitrones 107 (48−100%; Scheme 47, a). The authors 274 recognize that the catalytic cycle is not clear.…”

Section: Generation Of Acyclicmentioning

confidence: 99%

“…274 The reaction proceeded in a variety of solvents such as CH 2 Cl 2 , benzene, and DMF and at a broad range of temperatures (RT−153 °C) for 6−24 h, leading to nitrones 107 (48−100%; Scheme 47, a). The authors 274 recognize that the catalytic cycle is not clear. However, based upon literature data, we assume that BF 3 is required to block the HO-nucleophilic center and stabilize the oxime species in the nitrone form (c), 275 A proposed mechanism for this reaction is similar to that suggested for the O-arylation of 61 (Scheme 30), but oxime 109 is believed to coordinate to the copper center by the oxime N atom due to the absence of steric hindrance at the metal center provided by the amino acid ligands in 63.…”

Section: Generation Of Acyclicmentioning

confidence: 99%

“…The reaction proceeded in a variety of solvents such as CH 2 Cl 2 , benzene, and DMF and at a broad range of temperatures (RT–153 °C) for 6–24 h, leading to nitrones 107 (48–100%; Scheme , a). The authors recognize that the catalytic cycle is not clear. However, based upon literature data, we assume that BF 3 is required to block the HO-nucleophilic center and stabilize the oxime species in the nitrone form (c), whereas CdI 2 activates the electrophile (b).…”

Section: Metal-mediated Reactions Of the Oxime Groupmentioning

confidence: 99%

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Metal-Involving Synthesis and Reactions of Oximes

et al. 2017

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This review classifies and summarizes the past 10-15 years of advancements in the field of metal-involving (i.e., metal-mediated and metal-catalyzed) reactions of oximes. These reactions are diverse in nature and have been employed for syntheses of oxime-based metal complexes and cage-compounds, oxime functionalizations, and the preparation of new classes of organic species, in particular, a wide variety of heterocyclic systems spanning small 3-membered ring systems to macroheterocycles. This consideration gives a general outlook of reaction routes, mechanisms, and driving forces and underlines the potential of metal-involving conversions of oxime species for application in various fields of chemistry and draws attention to the emerging putative targets.

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Section: Metal-mediated Reactions Of the Oxime Groupmentioning

confidence: 96%

Section: Generation Of Acyclicmentioning

confidence: 99%

Section: Generation Of Acyclicmentioning

confidence: 99%

Section: Metal-mediated Reactions Of the Oxime Groupmentioning

confidence: 99%

See 2 more Smart Citations

Metal-Involving Synthesis and Reactions of Oximes

et al. 2017

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“…Oximes and their derivatives are important intermediates in the synthesis of amides [1][2][3][4], nitro compounds, hydroximinoyl chlorides, nitrones [5], amines, azoles, nitrile oxides, chiral -sulfinyl oximes, nitriles [6][7][8], and isoxazolines [9].…”

Section: Introductionmentioning

confidence: 99%

Emeraldine Base Form of Polyaniline Nanofibers as New, Economical, Green, and Efficient Catalyst for Synthesis of Z-Aldoximes

Boddula

Srinivasan

2014

Journal of Catalysts

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A facile, clean, economical, efficient, and green process was developed for the preparation of Z-aldoximes at room temperature under solvent-free condition using emeraldine base form of polyaniline as novel catalyst. In this methodology, PANI base absorbed the by-product of HCl (polluting chemical) from hydroxylamine hydrochloride and converted to polyaniline-hydrochloride salt (PANI-HCl salt). This PANI-HCl salt could be easily recovered and used in new attempts without any purification in many areas such as catalyst, electrical and electronics applications meant for conducting polymers. As far as our knowledge is concerned, emeraldine base as catalyst in organic synthesis for the first time.

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Conjugate Addition of Hydroxylamines, Oximes and Hydroxamic Acids

Du¹,

Mao²,

Zhang‐Negrerie³

et al. 2010

Patai's Chemistry of Functional Groups

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The conjugate addition of hydroxylamines, oximes and hydroxamic acids provides convenient route to incorporate an NO moiety into various Michael acceptors. This chapter reviews comprehensive experimental reactions on the formation of carbon–nitrogen and carbon–oxygen bonds via conjugate addition of hydroxylamines, oximes and hydroxamic acids to alkenes, alkynes or allenes attached to one or more electron‐withdrawing groups. Hydroxylamine derivatives predominantly undergo N‐centered conjugate addition, while for the ambient nucleophilic oximes and hydroxamic acids, both N‐centered and O‐centered conjugate addition are operative by control of the reaction conditions. A concerted cycloaddition mechanism has been well established for the conjugate addition of N ‐substituted hydroxylamines. The last decade has witnessed enormous growth in enantioselective conjugate addition of hydroxylamine derivatives and the O‐centered oximes. General Introduction Conjugate Addition of Hydroxylamine and Itsderivatives Conjugate Addition of Oximes Conjugate Addition of Hydroxamic Acids Conclusions Acknowledgments

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Synthesis of alkyl nitrones by reaction of aldehyde and ketone oximes with α,β-unstaturated esters in the presence of Lewis acid

Cited by 6 publications

References 15 publications

Metal-Involving Synthesis and Reactions of Oximes

Metal-Involving Synthesis and Reactions of Oximes

Emeraldine Base Form of Polyaniline Nanofibers as New, Economical, Green, and Efficient Catalyst for Synthesis of Z-Aldoximes

Conjugate Addition of Hydroxylamines, Oximes and Hydroxamic Acids

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