Chemoselectivity of the CuAAC/Ring Cleavage/Cyclization Reaction between Enaminones and α-Acylketenimine

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2190 - 2199

Published: Jan. 27, 2024

Ketenimines represent an important class of reactive species, useful synthetic intermediates, and synthons. However, in general, ketenimines preferentially undergoes nucleophilic addition reactions with hydroxyl amino groups, carbon functional groups remain a less studied subset such systems. Herein, we develop straightforward syntheses pyridin-4(1H)-imines that is achieved by cyclization reacting enaminone unit α-acylketenimine which generated from the sulfonyl azides terminal ynones situ (CuAAC/Ring cleavage reaction). The cascade process starts α-C instead group, attacking electron-deficient central ketenimine, chemoselectivity unconventional products were formed intramolecular cyclization.

Language: Английский

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Synthesis of 3-sulfonylisoindolin-1-ones from olefinic amides and sodium sulfinates via electrooxidative tandem cyclization

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(29), P. 5897 - 5901

Published: Jan. 1, 2024

Sulfonyl groups are motifs that widely found in biologically active compounds and drug molecules, many isolated natural products as well pharmaceuticals contain sulfonyl groups. Herein, we present the synthesis of sulfonyl-substituted isoindolones by a electrochemical oxidative radical cascade cycloaddition reaction olefinic amides with sodium sulfite under oxidant- catalyst-free conditions. Various sulfinates were compatible gave desired yields up to 99%.

Language: Английский

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Hydrogen bond-promoted regio- and stereoselective synthesis of isoindoline derivatives through Pd-catalyzed isocyanide insertion reaction involving aziridines

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(6), P. 1775 - 1781

Published: Jan. 1, 2024

We have successfully demonstrated an efficient and practical Pd-catalyzed reaction between aziridine isocyanide, leading to the synthesis of isoindoline derivatives in moderate good yields.

Language: Английский

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Palladium-catalyzed ligand-regulated divergent synthesis of pyrrole[2,3-b]indoles and ureas from 2-ethynylanilines and isocyanides

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(21), P. 2950 - 2953

Published: Jan. 1, 2024

A convenient and straight-forward entry to pyrrole[2,3- b ]indoles ureas via ligand-controlled palladium-catalyzed chemoselective tandem reaction of 2-ethynylanilines isocyanides has been established.

Language: Английский

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[1,2]‐Phospha‐Brook Rearrangement‐Initiated Palladium‐Catalyzed Cyclization Reaction of Isocyanides and o‐Bromobenzaldehydes: Access to 2H‐Isoindole‐1‐carboxamides and 2H‐Isoindole‐1‐carbonitriles

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 20, 2024

Comprehensive Summary Herein, a [1,2]‐phospha‐Brook rearrangement‐initiated palladium‐catalyzed cyclization reaction for base‐controlled selective synthesis of 2 H ‐isoindole‐1‐carboxamide and ‐isoindole‐1‐carbonitrile derivatives has been described. This strategy features double isocyanide insertion, efficient bond combinations, simple operation conditions. Mechanistic studies show that the rearrangement is key step in this reaction. protocol offers novel concise ‐isoindole derivatives.

Language: Английский

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Copper‐Catalyzed Photoinduced [3+3] Cycloaddition Reactions of α‐Acidic Isocyanides with Tetrazoles

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(21), P. 3611 - 3615

Published: Sept. 14, 2023

Abstract Herein, a copper‐catalyzed photoinduced [3+3] cycloaddition reaction of α‐acidic isocyanides with 2,5‐diaryltetrazoles is described. The proceeded smoothly high regioselectivity, affording range important 1,2,4‐triazines under mild conditions. obtained were converted into triazine alcohol, Weinreb amide and triazinone easily, which further illustrate the utility this process.

Language: Английский

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Atom-economic metal free mediated difunctionalization of isocyanides with 3-methyleneoxindoles and 3-methylene-benzofuranones

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5868 - 5875

Published: Jan. 1, 2024

We presented metal-free cascade reactions of isocyanides with 3-methyleneoxindoles and 3-methylenebenzofuranones via the cleavage chemically inert carbon–nitrogen bond or carbon–oxygen bond.

Language: Английский

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Radical-Initiated Dearomative Annulation of Tryptamine-Derived Isocyanides: Selective Synthesis of CF₃-Substituted β-Aza-spiroindolines and β-Carbolines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15979 - 15989

Published: Oct. 22, 2024

A mild approach for synthesizing CF3-substituted β-aza-spiroindolines and β-carbolines from tryptamine-derived isocyanides via site-selective radical annulations has been reported. The crucial role of C2 substituents in the selective annulation process clarified. shows good generality practical applicability, highlighting its effectiveness versatility.

Language: Английский

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Palladium-catalyzed Cascade Cyclization of Isocyanides with Di-(o-iodophenyl)sulfonylguanidines: Access to Heterocyclic Fused Quinazolines

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A palladium-catalyzed cascade cyclization reaction of di-

Language: Английский

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Isocyanide‐Based One‐Pot Cascade Synthesis of 3‐Acyl Isoindolinones^†

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 42(3), P. 259 - 263

Published: Sept. 21, 2023

Comprehensive Summary A series of 3‐acyl‐substituted isoindolinone derivatives were synthesized in a one‐pot manner via the reaction o ‐bromobenzaldehydes, isocyanides, and carboxylic acids presence palladium catalyst base. The employing easily available starting materials features simple operation high efficiency. mechanistic study showed that might undergo 1) Pd‐catalyzed [3+2] cyclization ‐bromobenzaldehyde with isocyanide re‐insertion another molecule isocyanide, 2) addition acid to situ formed ketenimine followed by rearrangement relay give 3,3‐diacyl‐substituted derivative. Further transformations obtained products through decarbonylation could also be realized.

Language: Английский

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