Efficient Synthesis of <i>N-</i>Alkylated α,β-Unsaturated Ketonitrones via Cu-Catalyzed Rearrangement

Nakamura, Itaru; Onuma, Toshiki; Kanazawa, Ryo; Nishigai, Yuki; Terada, Masahiro

doi:10.1021/ol501889g

Cited by 25 publications

(13 citation statements)

References 29 publications

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“…90 N-Alkylated α,β-unsaturated ketonitrones are synthesized from propargyloxyamines using CuI catalysts (eq 21). 91 This reaction can be rationalized by assuming copper-catalyzed intramolecular hydroamination, followed by electrocyclic ring opening of 3-isoxazoline.…”

Section: Reaction With Allenes Acetylenes and Alkenesmentioning

confidence: 99%

Synthesis and Transformations of Nitrones for Organic Synthesis

2019

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Nitrones are important compounds and are highly useful in many aspects. The first part describes the methods for synthesis of nitrones, which are useful and environmentally friendly. Catalytic oxidations, condensations, and other useful reactions are described. The nitrones thus obtained are key intermediates for the synthesis of biologically important nitrogen compounds. The second part describes the fundamental transformations of nitrones, which will provide the strategies and means for the construction of nitrogen compounds. The reactions with nucleophiles or radicals, C–H functionalization, and various addition reactions are described. The last reactions are particularly important for highly selective carboncarbon bond formations. 1,3-Dipolar cycloaddition reactions are excluded because the size of the review is limited and excellent reviews have been published in Chemical Reviews.

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Section: Reaction With Allenes Acetylenes and Alkenesmentioning

confidence: 99%

Synthesis and Transformations of Nitrones for Organic Synthesis

2019

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“…Scheme-17: Synthesis of New N-Oxides From Alkynes 3. A new synthetic route for the synthesis of N-alkylated α,β-unsaturated ketonitrones is recently reported by Terada et al 22 They have used propargyloxyamines as the precursor in the presence of CuI catalysts in the synthesis of nitrone. The reaction can be rationalized by assuming coppercatalyzed intramolecular hydroamination followed by electrocyclic ring-opening of 3-isoxazoline (Scheme-18).…”

Section: Synthesis Of Nitronesmentioning

confidence: 99%

Recent Advances in the Synthesis of Specialized Heterocyclic Molecules by 1, 3-Dipolar Cycloaddition Reaction: A Study Based on Greener Protocols

Chakraborty¹

2019

RJC

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In today's scenario trying newer methods or concepts in organic synthesis leading to the generation of new heterocycles and also saving the environment is equally challenging indeed for an organic chemist. Keeping in mind we feel that "green chemistry" methodologies are the need of the hour to save our environment and mankind. The aim of this review is to provide an overview of green chemistry protocols for the synthesis of a new class of specialized heterocyclic molecules via 1,3-dipolar cycloaddition reaction. In the present review, particular attention has been focused on the application of mechanochemical procedures and the use of green solvents. In addition, the review also includes reactions performed in ionic liquids, microwave-induced reactions, aqueous phase synthesis and light-induced reactions reported recently. This account also reports about the recent green synthetic methodologies of new nitrones and their cycloaddition reactions performed in our and other laboratories. We have also explored several protocols of atom efficient reactions of nitrones and further application of cycloadducts using green chemistry methodologies. The advantages of these procedures over existing conventional methodologies and the effect of solvents have been focused in this review to highlight different aspects of environmental issues and also in the selectivity of the reactions.

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“…The reaction proceeded through a copper-catalyzed intramolecular hydroamination and sequential thermal N-O bond cleavage of the resulting propargyloxyamine (Scheme 56). 45 The pathway for the formation of these ketonitrones was proposed on the basis of the isolation of 117 as a precursor to the acyclic nitrone (Scheme 57). The alkyne 115 was activated by the π-acidic copper catalyst to give intermediate A.…”

Section: Scheme 55 Copper-catalyzed Synthesis Of αβ-Epoxyketiminesmentioning

confidence: 99%

“…The corresponding 2-isoxazolines, with a quaternary carbon center, were obtained in excellent yields. 45…”

Section: Scheme 57 Proposed Pathway For the Formation Of N-alkyl Nitrmentioning

confidence: 99%

Recent Advances in the Arylation and Alkenylation of N–O Bonds

Jiao

et al. 2016

Synthesis

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Efficient Synthesis of N-Alkylated α,β-Unsaturated Ketonitrones via Cu-Catalyzed Rearrangement

Abstract: N-Alkylated unsaturated ketonitrones were efficiently synthesized from propargyloxyamines using Cu catalysts. Mechanistic studies suggest that the rearrangement reaction proceeds via Cu-catalyzed intramolecular hydroamination, followed by thermally induced electrocyclic ring opening.

Cited by 25 publications

References 29 publications

Synthesis and Transformations of Nitrones for Organic Synthesis

Synthesis and Transformations of Nitrones for Organic Synthesis

Recent Advances in the Synthesis of Specialized Heterocyclic Molecules by 1, 3-Dipolar Cycloaddition Reaction: A Study Based on Greener Protocols

Recent Advances in the Arylation and Alkenylation of N–O Bonds

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