Hypervalent iodine mediated synthesis of di- and tri-substituted isoxazoles via [3+2] cycloaddition of nitrile oxides

Singhal, Ankur; Parumala, Santosh Kumar Reddy; Sharma, Arun; Peddinti, Rama Krishna

doi:10.1016/j.tetlet.2015.10.038

Cited by 26 publications

(16 citation statements)

References 68 publications

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“…In previously reported cycloadditions of aldoximes with alkenes or alkynes using hypervalent iodine(III) species, most obtained compounds were 3,5‐disubstituted products as major isomers (Scheme , Equation 1). [6a], [6d], Previously, our research group reported that the oxidative cycloaddition of aldoximes using heterocyclic alkenes gave the corresponding 3,4,5‐trisubstituted products in moderate to good yields (Scheme , Equation 2). [9b], [11b] However, to the best of our knowledge, hypervalent iodine(III) reagent mediated regioselective synthesis of 3,4‐disubstituted isoxazoles from aldoximes with unsaturated compounds has not been developed.…”

Section: Introductionmentioning

confidence: 99%

Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones

et al. 2019

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An efficient oxidative cycloaddition of enaminones with nitrile oxides generated in situ from respective aldoximes using hypervalent iodine reagents has been developed. Reactions of various aldoximes with enaminones in the presence of [hydroxy(tosyloxy)iodo]benzene involved the regioselective cycloaddition reaction resulting in the formation of the 3,4‐disubstituted isoxazoles in moderate to good yields. Structures of several isoxazole products were confirmed by a single X‐ray crystallography.

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Section: Introductionmentioning

confidence: 99%

Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones

et al. 2019

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“…Isoxazoles belong to an important class of heteroaromatic compounds with many practical applications. 52 Hypervalent iodine reagents such as (diacetoxyiodo)benzene, 116,122,[142][143][144][145][146][147] [bis(trifluoroacetoxy)iodo]benzene, 136,[148][149][150][151] iodosylbenzene, 134,135 [hydroxy(tosyloxy)iodo]benzene, 152,153 and in situ generated iodine(III) species 138,154 have been commonly used for isoxazole ring construction.…”

Section: Synthesis Of Isoxazolesmentioning

confidence: 99%

Synthesis of Oxazoline and Oxazole Derivatives by Hypervalent-Iodine-Mediated Oxidative Cycloaddition Reactions

et al. 2020

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Organohypervalent iodine reagents are widely used for the preparation of various oxazolines, oxazoles, isoxazolines, and isoxazoles. In the formation of these heterocyclic compounds, hypervalent iodine species can serve as the activating reagents for various substrates, as well as the heteroatom donor reagents. In recent research, both chemical and electrochemical approaches toward generation of hypervalent iodine species have been utilized. The in situ generated active species can react with appropriate substrates to give the corresponding heterocyclic products. In this short review, we summarize the hypervalent-iodine-mediated preparation of oxazolines, oxazoles, isoxazolines, and isoxazoles starting from various substrates.1 Introduction2 Synthesis of Oxazolines3 Synthesis of Oxazoles4 Synthesis of Isoxazolines5 Synthesis of Isoxazoles6 Conclusion

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“…[17][18][19] In particular, the reaction of various aldoximes with alkynes in the presence of organohypervalent iodine(III) reagents such as DIB, 48,51,[54][55][56][57] BTI, 46,58,59 Koser's reagent, 49,60 or PhIO, 27,61 leads to oxidative heterocyclization yielding the corresponding isoxazoles. This procedure is applicable to various internal or terminal alkynes under mild condition.…”

Section: Cycloaddition Of Aldoximes Leading To Isoxazolesmentioning

confidence: 99%

“…© ARKAT USA, Inc Several oxidative cycloaddition reactions of internal alkynes with aldoximes using iodine(III) reagents have been reported. 46,54,60 The reactions of strained cyclic alkynes such as cyclooctyne derivatives with nitrile oxides generated from aldoximes and iodine(III) reagents are especially important in bioorthogonal chemistry. [55][56][57][58] For example, the reaction of lactose oxime with dibenzocyclooctyne derivatives using DIB gives the corresponding isoxazoles in good yields.…”

Section: Cycloaddition Of Aldoximes Leading To Isoxazolesmentioning

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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Hypervalent iodine mediated synthesis of di- and tri-substituted isoxazoles via [3+2] cycloaddition of nitrile oxides

Cited by 26 publications

References 68 publications

Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones

Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones

Synthesis of Oxazoline and Oxazole Derivatives by Hypervalent-Iodine-Mediated Oxidative Cycloaddition Reactions

Oxidative cyclizations of oximes using hypervalent iodine reagents

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