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3 article(s) from Hanusek, Jiří

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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[3 + 2]-Cycloaddition reaction of sydnones with alkynes

Veronika Hladíková,
Jiří Váňa and
Jiří Hanusek

Beilstein J. Org. Chem. 2018, 14, 1317–1348, doi:10.3762/bjoc.14.113

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Scheme 1: Thermal reaction of sydnones with symmetrical alkynes.

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Scheme 2: Reaction of sydnones with strained cycloalkynes.

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Scheme 3: Reaction of sydnones with didehydrobenzenes.

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Scheme 4: Formation of isomeric pyrazole dicarboxylates.

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Scheme 5: Mechanism of thermal cycloaddition between sydnones and alkynes.

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Scheme 6: Mechanism of photochemical reaction of sydnones with symmetrical alkynes.

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Scheme 7: HOMO–LUMO diagram for thermal [3 + 2]-cycloaddition of sydnones with alkynes.

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Scheme 8: Synthetic strategy leading to 1,2-disubstituted pyrazoles.

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Scheme 9: Unsuccessful reaction with phenylpropiolic acid.

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Scheme 10: Synthetic strategy leading to 1,4,5-trisubstituted pyrazoles.

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Scheme 11: Reaction of sydnones carrying in position 4- six-membered 2-N-heterocyclic ring.

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Scheme 12: Strain-promoted sydnone alkyne cycloaddition (SPSAC).

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Scheme 13: Synthesis of a key intermediate of niraparib.

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Scheme 14: Reaction of sydnones with 1,3-/1,4-benzdiyne equivalents.

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Scheme 15: Reaction of sydnones with heterocyclic strained cycloalkynes.

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Scheme 16: Mono-copper catalyzed cycloaddition reaction.

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Scheme 17: Di-copper catalyzed cycloaddition reaction.

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Published 05 Jun 2018

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