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2 article(s) from Marek, Lukáš

Eschenmoser coupling reactions starting from primary thioamides. When do they work and when not?

Lukáš Marek,
Jiří Váňa,
Jan Svoboda and
Jiří Hanusek

Beilstein J. Org. Chem. 2023, 19, 808–819, doi:10.3762/bjoc.19.61

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Scheme 1: Eschenmoser coupling reaction between 3-substituted oxindoles and thioamides.

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Scheme 2: Possible reactions of α-haloketones, esters and amides with primary thioamides.

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Figure 1: Studied α-bromoamides and α-bromolactams.

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Scheme 3: Reaction of 4-bromo-1,1-dimethyl-1,4-dihydroisoquinolin-3(2H)-one (2b) with thiobenzamide and thioa...

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Scheme 4: Reaction of 4-bromo-1,1-dimethyl-1,4-dihydroisoquinolin-3(2H)-one (2b) with 4’-substituted thiobenz...

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Scheme 5: Reaction of 4-bromoisoquinoline-1,3(2H,4H)-dione (3) with thiobenzamide, thioacetamide, and thioben...

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Scheme 6: Reaction of N-phenyl- and N-methyl-2-bromo(phenyl)acetamide (4a,b) with thiobenzamide in acetonitri...

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Scheme 7: Transformation of salt 15 under kinetic and thermodynamic control conditions [1].

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Figure 2: Comparison of energy profiles (relative Gibbs energies at 298 K in kJ·mol⁻¹ for the ECR (right) and...

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Published 09 Jun 2023

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Synthesis of (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2H-indol-2-ones using an Eschenmoser coupling reaction

Lukáš Marek,
Lukáš Kolman,
Jiří Váňa,
Jan Svoboda and
Jiří Hanusek

Beilstein J. Org. Chem. 2021, 17, 527–539, doi:10.3762/bjoc.17.47

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Figure 1: Nintedanib ethanesulfonate.

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Scheme 1: The known synthetic strategies leading to 3-(aminomethylidene)oxindoles.

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Scheme 2: The possible intermediates and products occurring in the reactions of 3-bromooxindoles with thioben...

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Figure 2: The R¹ and R² substitution influence on the isolated yields of products 5aa–ed.

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Scheme 3: The Eschenmoser coupling reaction of 3-bromooxindole (1a) with thioacetamides.

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Scheme 4: The synthesis of alternative 3-substituted oxindoles and their Eschenmoser coupling reaction with t...

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Published 23 Feb 2021

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