Unusual Lewis-acid catalyzed formal (3+3)-cycloaddition of azomethine imines and nitrones to N-vinylpyrroles

Efremova, Mariia M.; Kostikov, R. R.; Stepakov, A. V.; Panikorovsky, Taras L.; Shcherbakova, V. S.; Иванов, А. В.; Molchanov, A. P.

doi:10.1016/j.tet.2016.12.034

Cited by 20 publications

(6 citation statements)

References 74 publications

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“…[3 + 3]-cycloaddition of vinyl pyrrole with azomethine imine. [36] [3 + 3]-cycloaddition of vinyl pyrrole with nitrone. [36]…”

Section: Discussionmentioning

confidence: 99%

“…Synthesis of 1,2,4-hexahydrotriazine derivative (36) was developed by Chao-Ze Zhu et alvia [Rh(NBD) 2 ]BF 4 catalyzed [3 + 3] cycloaddition reaction of (R)-vinyl aziridines (34) with Nimino isoquinolium ylide (35) (Scheme 12). [23] The product was formed through consecutive (б + п) rhodium species subse- [3 + 3]-cycloaddition reaction of α-acidic isocyanide with azomethine imine in presence of Cu catalyst.…”

Section: Metal Catalyzed Approachmentioning

confidence: 99%

“…A. P. Molchanov and groups developed a [3+3]‐cycloaddition reaction for the formation of pyrazolo[1,2‐a]pyrrolo[1,2‐d][1,2,4]triazine ( 66 ) and pyrrolo[2,1‐d][1,2,5]oxadiazine in presence of Lewis acid catalyst with moderate yield (Scheme ) . It was observed that, the core of pyrazolo[1,2‐a]pyrrolo[1,2‐d][1,2,4]triazin‐7(11H)‐one found along with the desired [3+3]‐cycloadduct product 66 and 67 via the reaction of azomethine imine 2 and vinyl pyrrole 65 in presence of Ni(ClO 4 ) 2 , 6H 2 O as a catalyst.…”

Section: Synthetic Route For [3+3] Cycloaddition Of Azomethine Iminementioning

confidence: 99%

“…A variety of nitrones ( 68 ) were treated with N‐vinylpyrroles under the optimized condition but in this case Ni(ClO 4 ) 2 ,6H 2 O (20 mol%) was the best catalyst at 80 °C to produce the diastereomeric mixture of pyrrolo[2,1‐d][1,2,5] oxadiazines with predominant cis product and the mixture of isomer was separated by column chromatography (Scheme ) . The relative configuration of cycloadduct product was confirmed by single crystal XRD‐analysis.…”

Section: Synthetic Route For [3+3] Cycloaddition Of Azomethine Iminementioning

confidence: 99%

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[3+3] Cycloaddition of Azomethine Imine: Synthesis of Bi‐ or Tricyclic N‐Heterocycle

Das

Daripa

et al. 2020

ChemistrySelect

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Synthesis of six-membered bicyclic, tricyclic or tetracyclic Nheterocycles are important due to enormous use of such scaffolds in bioactive natural products, agrochemicals and in pharmaceuticals. [3 + 3] cycloaddition of azomethine imine for the construction of such heterocycles is less explored but also a genuine approach with the other method like [4 + 2] and [2 + 2 + 2] cycloaddition. Hence, the literature survey in this area is utmost significant. The delights and difficulties of [3 + 3] cycloaddition of azomethine imine have been deliberated thoroughly to elucidate this highly mounting field in this literature study. Herein, we report a vast synthetic method [base catalyzed, metal catalyzed (racemic and asymmetric), phosphine catalyzed, NHC and Lewis acid catalyzed] for the synthesis of di, tri and tetra-nitrogen containing heterocycles via [3 + 3] cycloadditon reaction of azomethine imine.

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“…[3 + 3]-cycloaddition of vinyl pyrrole with azomethine imine. [36] [3 + 3]-cycloaddition of vinyl pyrrole with nitrone. [36]…”

Section: Discussionmentioning

confidence: 99%

Section: Metal Catalyzed Approachmentioning

confidence: 99%

Section: Synthetic Route For [3+3] Cycloaddition Of Azomethine Iminementioning

confidence: 99%

Section: Synthetic Route For [3+3] Cycloaddition Of Azomethine Iminementioning

confidence: 99%

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[3+3] Cycloaddition of Azomethine Imine: Synthesis of Bi‐ or Tricyclic N‐Heterocycle

Das

Daripa

et al. 2020

ChemistrySelect

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“…In the absence of a Lewis acid catalyst normal [3+2] cycloaddition took place (Scheme 30). 74 Metal-free [3+3] cycloadditions of dipoles 47 and 49 and their 4,4-dimethyl analog 101 catalyzed by DABCO have been reported with 1,4-dithiane-2,5-diol (102) to give highly functionalized tetrahydropyrazolo[1,2-c][1,3,4]thia-diazinones 103 in good yields with excellent diastereoselectivity (Scheme 31). 75 Similarly, N-heterocyclic carbene L17-catalyzed cycloaddition of 49 to enals 104 afforded cycloadducts 105 as single diastereomers in good yields.…”

Section: Syn Thesismentioning

confidence: 99%

Copper-Catalyzed Azomethine Imine–Alkyne Cycloadditions (CuAIAC)

Grošelj

Požgan²,

Štefane³

et al. 2018

Synthesis

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Although the first example of copper-catalyzed azomethine imine–alkyne cycloaddition (CuAIAC) was published only a year after the seminal papers of Meldal and Sharpless on Cu-catalyzed azide–alkyne cycloaddition (CuAAC), the CuAIAC reaction has remained overlooked by the synthetic community for almost a decade. Since 2010, however, CuAIAC reaction started to emerge as a promising supplement to the well-known CuAAC reaction. The present review surveys primarily the literature on CuAIAC reaction since 2003. Beside this, azomethine imine–alkyne cycloadditions catalyzed by other metals, selected examples of metal-free reactions, and related [3+3] and [3+4] cycloadditions of azomethine imines are presented. All these experimental data indicate the viability of CuAIAC in organic synthesis and the applicability in ‘click’ chemistry.1 Introduction2 Reactions with Acyclic Azomethine Imines3 Reactions with C,N-Cyclic Azomethine Imines4 Reactions with N,N-Cyclic Azomethine Imines5 Reactions with C,N,N-Cyclic Azomethine Imines6 The Mechanism of the CuAIAC Reaction7 Conclusions and Outlook

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Reactions of Aldehydes and Ketones and their Derivatives

Hussaini

2020

Organic Reaction Mechanisms Series

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Unusual Lewis-acid catalyzed formal (3+3)-cycloaddition of azomethine imines and nitrones to N-vinylpyrroles

Cited by 20 publications

References 74 publications

[3+3] Cycloaddition of Azomethine Imine: Synthesis of Bi‐ or Tricyclic N‐Heterocycle

[3+3] Cycloaddition of Azomethine Imine: Synthesis of Bi‐ or Tricyclic N‐Heterocycle

Copper-Catalyzed Azomethine Imine–Alkyne Cycloadditions (CuAIAC)

Reactions of Aldehydes and Ketones and their Derivatives

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