1,3-Dipolar Cycloaddition Reactions of Stable Bicyclic and Monocyclic Azomethine Ylides: Preparative Aspects

Elender, Kurt; Nöth, Heinrich; Riebel, Peter; Weber, Andreas; Sauer, Jürgen

doi:10.1016/s0040-4020(00)00453-1

Cited by 12 publications

(2 citation statements)

References 8 publications

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“…The stable dicyanoazomethine ylides 257, derived from reaction of 3,4-diazanorcaradienes 255 with tetracyanoethylene oxide 256 [148], undergo reaction with a range of dipolarophiles [149]. The carbonyl dipolarophile trichloroacetaldehyde (2g) undergoes efficient cycloaddition with ylide 257 to give cycloadduct 258 isolated as a single endo stereoisomer in 40% yield (Scheme 75).…”

Section: Reactions Of Dicyanoazomethine Ylidesmentioning

confidence: 99%

1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives

Meyer

Ryan

2016

Molecules

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Abstract:We provide a comprehensive account of the 1,3-dipolar cycloaddition reactions of azomethine ylides with carbonyl dipolarophiles. Many different azomethine ylides have been studied, including stabilized and non-stabilized ylides. Of the carbonyl dipolarophiles, aldehydes including formaldehyde are the most studied, although there are now examples of cycloadditions with ketones, ketenes and carboxyl systems, in particular isatoic anhydrides and phthalic anhydrides. Intramolecular cycloadditions with esters can also occur under certain circumstances. The oxazolidine cycloadducts undergo a range of reactions triggered by the ring-opening of the oxazolidine ring system.

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Section: Reactions Of Dicyanoazomethine Ylidesmentioning

confidence: 99%

1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives

Meyer

Ryan

2016

Molecules

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“…[1][2][3][4][5][6][7][8][9][10][11][12][13] Cycloaddition reactions between pyridazinium phenacylides and symmetrical N-substituted maleimides were first reported in 1979 14 but the stereochemistry of the ensuing cycloadducts was investigated only more recently. 10-13 Herein we report the 1,3-dipolar cycloaddition reaction between pyridazinium N-ylides 4 and the non-symmetrical 3-methyl-N-phenylmaleimide 5 giving the cycloadducts 6 and 7.…”

Section: Introductionmentioning

confidence: 99%

Endo and regioselectivity in 1,3-dipolar cycloaddition of pyridazinium N-ylides with a non-symmetrical cyclic olefin

Dumitraşcu¹,

Caira²,

Drăghici³

et al. 2008

Arkivoc

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The 1,3-dipolar cycloaddition between pyridazinium N-ylides 3 and 3-methyl-Nphenylmaleimide was studied. In the case of pyridazinium phenacylides 4a-c the reaction was endo and regioselective, while in the case of carbomethoxymethylide 4d the cycloaddition gave two endo isomers in a 2:1 ratio. The stereochemistry of the adducts 6a-c and 7a,b was determined by NMR spectroscopy and confirmed by X-ray analysis for a representative compound, namely 6b.

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Cyclooctyne

Harris

Alabugin

2017

Encyclopedia of Reagents for Organic Synthesis

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1,3-Dipolar Cycloaddition Reactions of Stable Bicyclic and Monocyclic Azomethine Ylides: Preparative Aspects

Cited by 12 publications

References 8 publications

1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives

1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives

Endo and regioselectivity in 1,3-dipolar cycloaddition of pyridazinium N-ylides with a non-symmetrical cyclic olefin

Cyclooctyne

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