Interaction of 1,5-Substituted Pyrrolin-2-ones with Dichlorocarbene under Phase Transfer Catalysis Conditions

Egorova, A. Yu.; Sedavkina, V. A.; Timofeyeva, Zlata Yu.

doi:10.3390/51001082

Cited by 3 publications

(3 citation statements)

References 1 publication

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“…In particular, we decided to shed light on the molecular mechanism of model transformations involving a representative series of conjugated nitroalkenes (1ae) and dichlorocarbene (2) (Scheme 1). Carbene 2 is well known and may be easily generated in the reaction environment [22][23][24][25]. On the other hand, five nitroalkenes (1ae) characterized by a different type of substitution were selected.…”

Section: Introductionmentioning

confidence: 99%

Competition between [2 + 1]- and [4 + 1]-cycloaddition mechanisms in reactions of conjugated nitroalkenes with dichlorocarbene in the light of a DFT computational study

Alnajjar

Jasiński

2019

J Mol Model

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The competition between [2 + 1] and [4 + 1] channels regarding reactions of conjugated nitroalkenes with dichlorocarbene was explored based on B3LYP/6-31G(d) calculations. It was found that, in the case of cycloadditions involving parent nitroethene and its 1-substituted analogs, the [2 + 1] scheme should be treated as possible only from the kinetic process point of view. On the other hand, in similar reactions involving 2-substituted nitroethenes, both channels considered may compete. Additionally, mechanistic aspects of all cycloadditions were analyzed. It was found that the considered [2 + 1]-cycloadditions proceed via a non-polar mechanism with a biradicaloidal transition state (TS), whereas [4 + 1]-cycloadditions proceed via a polar mechanism with a zwitterionic TS.

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Section: Introductionmentioning

confidence: 99%

Competition between [2 + 1]- and [4 + 1]-cycloaddition mechanisms in reactions of conjugated nitroalkenes with dichlorocarbene in the light of a DFT computational study

Alnajjar

Jasiński

2019

J Mol Model

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“…Carbonyldiimidazole 349 was prepared in 87% yield via reaction of imidazole 347 with phosgene 348 under PTC condition (chlorobenzene/NaOH/ tributylhexadecylphosphonium bromide (TBHDPB)) [110] ( Figure 123).…”

Section: N-carbonylationmentioning

confidence: 99%

“…Treatment of 5-alkyl(aryl)-3H-pyrrolin-2-ones 391 with dichlorocarbene using (CHCl 3 /NaOH/ BTEAB) at 20-30 ∘ C afforded the intermediates 1-alkyl-6,6-dichloro-2-azabicyclo[3.1.0]hexan-3-ones which directly rearranged and dehydrochlorinated to give 6-alkyl(aryl)-1phenyl-5-oxohydropyridin-2-ones 392 [110] (Figure 130).…”

Section: Ring Expansionmentioning

confidence: 99%

Synthesis and Reactions of Five-Membered Heterocycles Using Phase Transfer Catalyst (PTC) Techniques

El-Sayed

Allah

El‐Saghier

et al. 2014

Journal of Chemistry

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Phase transfer catalysts (PTCs) have been widely used for the synthesis of organic compounds particularly in both liquid-liquid and solid-liquid heterogeneous reaction mixtures. They are known to accelerate reaction rates by facilitating formation of interphase transfer of species and making reactions between reagents in two immiscible phases possible. Application of PTC instead of traditional technologies for industrial processes of organic synthesis provides substantial benefits for the environment. On the basis of numerous reports it is evident that phase-transfer catalysis is the most efficient way for generation and reactions of many active intermediates. In this review we report various uses of PTC in syntheses and reactions of five-membered heterocycles compounds and their multifused rings.

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Reactivity of pyrrol-2-ones. (review)

Egorova

Timofeeva

2004

Chem Heterocycl Compd

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Published data on the chemical transformations of pyrrol-2-ones are reviewed and analyzed. The extensive synthetic possibilities of compounds containing a pyrrolone ring in the synthesis of various heterocyclic compounds with complex structures are demonstrated. The reactions are arranged according to the reaction centers of the pyrrol-2-ones: The methylene unit, the C=C double bond, the electron-deficient carbon atom of the carbonyl group.

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Interaction of 1,5-Substituted Pyrrolin-2-ones with Dichlorocarbene under Phase Transfer Catalysis Conditions

Abstract: Treatment of 5-alkyl(aryl)-3H-pyrrolin-2-ones with dichlorocarbene under phase transfer catalysis conditions at 20-30ºC results in a cycloaddition of the carbene to the C=C bond followed by skeletal rearrangement.

Cited by 3 publications

References 1 publication

Competition between [2 + 1]- and [4 + 1]-cycloaddition mechanisms in reactions of conjugated nitroalkenes with dichlorocarbene in the light of a DFT computational study

Competition between [2 + 1]- and [4 + 1]-cycloaddition mechanisms in reactions of conjugated nitroalkenes with dichlorocarbene in the light of a DFT computational study

Synthesis and Reactions of Five-Membered Heterocycles Using Phase Transfer Catalyst (PTC) Techniques

Reactivity of pyrrol-2-ones. (review)

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