Convenient synthesis of spiroindolenines from tryptamine-derived isocyanides and organic azides by cobalt catalysis in pure water

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(7), P. 2619 - 2623

Published: Jan. 1, 2021

A sustainable synthesis of spiroindolenines from tryptamine-derived isocyanides and organic azides in pure water was described.

Language: Английский

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C—F Bond Insertion into Indoles with CHBr₂F: An Efficient Method to Synthesize Fluorinated Quinolines and Quinolones

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(10), P. 1128 - 1132

Published: Feb. 6, 2024

Comprehensive Summary A mild and practical method for synthesizing fluorinated quinoline derivatives, which have a wide range of applications in pharmaceuticals, materials, organic synthesis, was described through C—F bond insertion into indoles using CHBr 2 F. The simple conditions, readily availability F, as well the versatility transformations make this strategy very powerful 3‐fluoroquinoline 3‐fluoroquinolone. mechanistic studies reveal that bromofluorocarbene generated in‐situ under basic condition key intermediate.

Language: Английский

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Visible-light-induced [1,3]-brook rearrangements of α-ketoacylsilanes and their subsequent trapping in a tandem annulation with 1,3,5-triazinanes and azomethine imines

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(11), P. 3250 - 3256

Published: Jan. 1, 2024

An unusual visible-light-induced [1,3]-brook rearrangement of α-ketoacylsilanes for cascade cyclization with 1,3,5-triazinanes and C , N -cyclic azomethine imines has been realized to assemble various β-lactams pyrazolidinone scaffolds.

Language: Английский

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Divergent Reaction of Isocyanides with o-Bromobenzaldehydes: Synthesis of Ketenimines and Lactams with Isoindolinone Cores

Organic Letters, Journal Year: 2021, Volume and Issue: 23(19), P. 7342 - 7347

Published: Sept. 15, 2021

A divergent reaction of isocyanides with o-bromobenzaldehydes for the synthesis isoindolinone-derived ketenimines and lactams was disclosed. The features readily available reactants, relatively mild conditions, high yields products. Ketenimines could be applied in further transformations access to other functional molecules. mechanism study showed that palladium-migration/imine-insertion process key step this reaction.

Language: Английский

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Palladium-catalysed imidoylative spirocyclization of 3-(2-isocyanoethyl)indoles

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(81), P. 10576 - 10579

Published: Jan. 1, 2021

A palladium-catalysed construction of spiroindolines through dearomative spirocyclization 3-(2-isocyanoethyl)indoles has been developed. 2'-Aryl-, vinyl-, and alkyl-substituted could be accessed under mild conditions with excellent functional group tolerance. C1-tethered oxindole- indole-spiroindoline bisheterocycles were generated in high yields via alkene/allene insertion an imidoylative cascade. Additionally, a tandem dearomatization two different indoles was realized N-(2-bromobenzoyl)indoles as the electrophilic coupling partner 3-(2-isocyanoethyl)indoles, affording polyindoline - spiroindoline bisheterocyclic scaffolds conveniently. Under catalysis Pd(OAc)2 spinol-derived phosphoramidite ligand, chiral successfully up to 95% yield 85% ee.

Language: Английский

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Brønsted Acid-Catalyzed Dehydrative Nazarov-Type Cyclization/C2–N1 Cleavage Cascade of Perfluoroalkylated 3-Indolyl(2-benzothienyl)methanols

Organic Letters, Journal Year: 2023, Volume and Issue: 25(27), P. 4956 - 4961

Published: June 29, 2023

A novel and unprecedented p-toluenesulfonic acid-catalyzed dehydrative Nazarov-type cyclization/C2-N1 bond cleavage cascade reaction of perfluoroalkylated 3-indolyl(2-benzothienyl)methanols has been developed. This provides an efficient practical protocol for the construction highly functionalized benzothiophene-fused cyclopentenones with exclusive stereoselectivity. In addition, this transformation also delineates a rare example involvement selective C2-N1 indoles.

Language: Английский

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N-Halosuccinimide enables cascade oxidative trifluorination and halogenative cyclization of tryptamine-derived isocyanides

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Oct. 16, 2024

Both the pyrroloindoline core and N-CF

Language: Английский

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Cobalt-Catalyzed Isocyanide-Based Three-Component Cascade for the Synthesis of Quinazolines

Organic Letters, Journal Year: 2021, Volume and Issue: 23(17), P. 6740 - 6744

Published: Aug. 12, 2021

A Co-catalyzed cyclization reaction of isocyanides, azides, and amines to access quinazoline derivatives was described. This protocol features a high atom economy, mild conditions, excellent yields, broad substrate scope. cascade involved three or four C–N bonds the formation one two rings. The quinazolin-4(H)-imines obtained are proven be versatile intermediates for further valuable transformations. It also found that cobalt catalyst could isolated from mixture reused.

Language: Английский

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Copper-Catalyzed One-Step Formation of Four C–N Bonds toward Polyfunctionalized Triazoles via Multicomponent Reaction

Organic Letters, Journal Year: 2022, Volume and Issue: 24(32), P. 6006 - 6012

Published: Aug. 5, 2022

A novel four-component reaction of alkynes, amines, azides, and 2H-azirines has been developed for the first time by efficient formation four C–N bonds in one step under mild conditions, rapidly preparing polyfunctionalized triazoles with molecular diversity involving three different intermediates copper–acetylide, copper–allenylidene, copper–vinyl nitrene. Propargylic ester is disclosed as a "three-in-one" building block possessing triplicate cycloaddition nucleophilic electrophilic properties, which could enable such transformation high yields, broad substrate scope, functionalization.

Language: Английский

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Diastereodivergent Synthesis of Pentacyclic Spiroindolines via a Magnesium(II)-Catalyzed Cascade Reaction of N,N′-Cyclic Azomethine Imines with Indolyl-Substituted Isocyanides

Organic Letters, Journal Year: 2023, Volume and Issue: 25(21), P. 3829 - 3834

Published: May 17, 2023

Magnesium(II)-catalyzed cascade reactions of N,N'-cyclic azomethine imines with indolyl-substituted isocyanides are reported herein. The method exhibited a high functional group tolerance and broad substrate scope. A series anti-pentacyclic spiroindolines containing N,N'-fused heterocycle skeletons were obtained in up to 82% yield 8.5:1 dr under mild reaction conditions. Intriguingly, sequential HOAc-mediated protonation results diastereoenriched epimerization, which gives rise the syn-pentacyclic as sole isomers.

Language: Английский

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