Hypervalent iodine-mediated interaction of aldoximes with activated alkenes including Baylis–Hillman adducts: a new and efficient method for the preparation of nitrile oxides from aldoximes

Das, Biswanath; Holla, Harish; Mahender, Gurram; Banerjee, Joydeep; Reddy, M. Ravinder

doi:10.1016/j.tetlet.2004.07.159

Cited by 69 publications

(45 citation statements)

References 16 publications

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“…Although the expected nitrile oxide dimerized product oxadiazole-N-oxides reported to be formed with other oxidizing and hypervalent iodine reagents 15 which is quite contrary to our observation. 9 Subsequently, we developed a facile, convenient method to prepare hydroxamic acids from various aromatic and aliphatic aldoximes using Koser's reagent.…”

Section: Resultscontrasting

confidence: 99%

A convenient one-pot synthesis of amines from aldoximes mediated by Koser’s reagent

Patel¹,

Ghosh²,

Baneerjee³

et al. 2011

Arkivoc

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A simple and convenient procedure has been developed for the synthesis of aromatic amine by a one-pot reaction of aromatic aldoxime with hypervalent iodine(III) reagent [hydroxy(tosyloxy)iodo]benzene (HTIB, Koser's reagent), in an alkaline medium. The aldoxime reacts with Koser's reagent to form an intermediate hydroxamic acid, which then undergoes Lossen type rearrangement to produce the desired amine. Several amines have been prepared which otherwise are difficult to prepare, by the reduction of corresponding nitro compounds. The scopes and limitations of this transformation have been discussed.

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Section: Resultscontrasting

confidence: 99%

A convenient one-pot synthesis of amines from aldoximes mediated by Koser’s reagent

Patel¹,

Ghosh²,

Baneerjee³

et al. 2011

Arkivoc

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“…Various practically important isoxazolines have been prepared by the reaction of aldoximes and alkenes using hypervalent iodine(III) reagents, such as iodosylbenzene (PhIO), 27 (diacetoxyiodo)benzene, 42,43 or (dichloroiodo)benzene. 39 For example, Das and co-workers reported the reaction of substituted benzaldoximes with DIB and alkenes to give the corresponding isoxazolines in good yields.…”

Section: Cycloaddition Of Aldoximes Leading To Isoxazolinesmentioning

confidence: 99%

“…39 For example, Das and co-workers reported the reaction of substituted benzaldoximes with DIB and alkenes to give the corresponding isoxazolines in good yields. 42 This procedure also works for the reaction of aldoximes 20 with Baylis-Hillman adducts 21 producing the corresponding functionalized isoxazoline products 22 in good yields (Scheme 5). This procedure is applicable to the heterocyclization reactions of aldoximes bearing sensitive substituents such as pyrazolyl aldoximes, 44 pinacol boronic acid ester benzaldoximes, 45 or (6-piperidin-1-yl-9H-purin-9-yl)acetaldehyde oxime.…”

Section: Cycloaddition Of Aldoximes Leading To Isoxazolinesmentioning

confidence: 99%

Oxidative cyclizations of oximes using hypervalent iodine reagents

Yoshimura

Zhdankin²

2017

Arkivoc

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This account overviews oxidative cyclization reactions of aldoximes or ketoximes promoted by hypervalent iodine reagents. The oxidation of aldoximes by iodine(III) compounds generates nitrile oxides which can further react with appropriate substrates via intermolecular or intramolecular 1,3-dipolar cycloaddition reactions leading to a variety of nitrogen and oxygen heterocycles. Hypervalent iodine reagents can also react with ketoximes producing the corresponding heterocyclic products via intramolecular cyclization reactions. Recently, the oxidative cyclization reactions of aldoximes have been realized under catalytic conditions mediated by hypervalent iodine active species.

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“…From the discovery of the DA reaction in the 1920s by Otto Diels and Kurt Alder [12], the new methods developed to give highly variable yields. Having low toxicity, ready availability, easy handling like iodine compounds, Iodobenzene (PhI) is the most utilized iodoarene, and m-chloroperbenzoic acid (mCPBA) and oxone are usually used as the terminal oxidants [13][14][15][16]. the lot of theoretical work has been devoted to the study of the mechanism and the selectivity of these cycloaddition reactions.…”

Section: Introductionmentioning

confidence: 99%

Understanding the Regioselective and Molecular Mechanism of the TCE in Cycloaddtion Reaction (TCE+Cp) and Addition Reaction (TCE+HCl) using DFT calculation

Zeroual¹,

Hajbi²

2016

Can Chem Trans

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Abstract:The polar Diels-Alder (P-DA) reaction of TCE (2,3-Dicyano-but-2-enedinitrile), diene Cp, toward Bicyclo[2. 2. 1]hept-5-ene-2, 2, 3, 3-tetracarbonitrile , was theoretically studied using DFT methods at the B3LYP/ 6-31G(d) level and 6-31G(d,p) in the presence of water. Calculated relative enthalpy associated with the two feasible reactive channels indicate that this P-DA cycloaddition takes place via C2-C3 regioselectivity, furnishing a formal [4+2] P1 in excellent agreement with experimental outcomes. In the considered P-DA reaction, while C2-C3 regioselectivity can be explained using calculated Parr functions at the interacting sites of reagents. In addition, Hydrochloric acid does not react with the TCE (2,3-Dicyano-but-2-enedinitrile) due to the high activation energy of this reaction.

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Hypervalent iodine-mediated interaction of aldoximes with activated alkenes including Baylis–Hillman adducts: a new and efficient method for the preparation of nitrile oxides from aldoximes

Cited by 69 publications

References 16 publications

A convenient one-pot synthesis of amines from aldoximes mediated by Koser’s reagent

A convenient one-pot synthesis of amines from aldoximes mediated by Koser’s reagent

Oxidative cyclizations of oximes using hypervalent iodine reagents

Understanding the Regioselective and Molecular Mechanism of the TCE in Cycloaddtion Reaction (TCE+Cp) and Addition Reaction (TCE+HCl) using DFT calculation

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