Substitution of 3H-furan-2-ones in amination and hydroamination reactions

Morozova, N. A.; Sedavkina, V. A.; Egorova, Yu.

doi:10.1007/bf01165696

Cited by 6 publications

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“…[11] Previously, the first representatives of the series of aminomethylidenefuranone derivatives were obtained by us by the reaction of 5-alkyl-3-formylfuran-2(3H)-ones with aniline. [12] It should be noted that the difficulties of introducing the formyl group into the furanone structure significantly limit this method for obtaining the aminomethylidenefuranone derivatives of the studied compounds. At the same time, orthoesters are convenient reagents in the molecular design and functionalization of heterocyclic compounds.…”

Section: Introductionmentioning

confidence: 99%

Study of E/Z isomerization of (arylamino)methylidenefuran‐2(3H)‐ones by ¹H, ¹³C, ¹⁵N spectroscopy and DFT calculations in different solvents

Осипов

Anis’kov

Grinev

et al. 2017

Magnetic Reson in Chemistry

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The structure and configuration of the series of previously unknown arylaminomethylidenefuran-2(3H)-ones have been determined in solution by H, C, N nuclear magnetic resonance spectroscopy including two-dimensional experiments such as H─ H COSY, dqCOSY, H─ C HSQC, H─ C HMBC. It was found that synthesized substances exist as an equilibrium mixture of E- and Z-enamines in solution. It was established on the basis of density functional theory calculations that the exchange between the two push-pull enamines is a simple rotation around an exocyclic partial double bond that depends on the effect of the solvents. Copyright © 2017 John Wiley & Sons, Ltd.

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Section: Introductionmentioning

confidence: 99%

Study of E/Z isomerization of (arylamino)methylidenefuran‐2(3H)‐ones by ¹H, ¹³C, ¹⁵N spectroscopy and DFT calculations in different solvents

Осипов

Anis’kov

Grinev

et al. 2017

Magnetic Reson in Chemistry

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“…5-R-3Н-Furan-2-ones [5] are convenient initial compounds for the synthesis of functionalized heterocyclic systems. The reaction of compounds 1а-1d with 1,3phenylenediamine and benzidine we investigated under different conditions.…”

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confidence: 99%

Synthesis of 1-substituted 5-alkyl(aryl)-1,3-dihydro-2H-pyrrol-2-ones. Azocoupling with diazonium salts

2016

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Reactions of 5-alkyl-and 5-aryl-3H-furan-2-ones with 1,3-and 1,4-binucleophiles of aromatic series were carried out for the first time under various conditions. In the presence of a base the reaction resulted in 1-R-1,3-dihydro-2Н-pyrrol-2-ones, under milder conditions intermediates were isolated, 4-aryl-4oxobutanamides. The structure of the latter was proved by spectral methods. By an example of 1-R-1,3dihydro-2Н-pyrrol-2-ones the possibility was demonstrated of their functionalization via introducing an aryldiazenyl fragment.

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Palladium-catalyzed C—O hydrogenolysis in γ-hydroxy γ-lactams as an efficient approach to 5-alkyl(aryl)pyrrolidin-2-ones

et al. 2015

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Substitution of 3H-furan-2-ones in amination and hydroamination reactions

Cited by 6 publications

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Study of E/Z isomerization of (arylamino)methylidenefuran‐2(3H)‐ones by ¹H, ¹³C, ¹⁵N spectroscopy and DFT calculations in different solvents

Study of E/Z isomerization of (arylamino)methylidenefuran‐2(3H)‐ones by ¹H, ¹³C, ¹⁵N spectroscopy and DFT calculations in different solvents

Synthesis of 1-substituted 5-alkyl(aryl)-1,3-dihydro-2H-pyrrol-2-ones. Azocoupling with diazonium salts

Palladium-catalyzed C—O hydrogenolysis in γ-hydroxy γ-lactams as an efficient approach to 5-alkyl(aryl)pyrrolidin-2-ones

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Substitution of 3H-furan-2-ones in amination and hydroamination reactions

Cited by 6 publications

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Study of E/Z isomerization of (arylamino)methylidenefuran‐2(3H)‐ones by 1H, 13C, 15N spectroscopy and DFT calculations in different solvents

Study of E/Z isomerization of (arylamino)methylidenefuran‐2(3H)‐ones by 1H, 13C, 15N spectroscopy and DFT calculations in different solvents

Synthesis of 1-substituted 5-alkyl(aryl)-1,3-dihydro-2H-pyrrol-2-ones. Azocoupling with diazonium salts

Palladium-catalyzed C—O hydrogenolysis in γ-hydroxy γ-lactams as an efficient approach to 5-alkyl(aryl)pyrrolidin-2-ones

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Study of E/Z isomerization of (arylamino)methylidenefuran‐2(3H)‐ones by ¹H, ¹³C, ¹⁵N spectroscopy and DFT calculations in different solvents

Study of E/Z isomerization of (arylamino)methylidenefuran‐2(3H)‐ones by ¹H, ¹³C, ¹⁵N spectroscopy and DFT calculations in different solvents