Sulfoximine Assisted C–H Activation and Annulation via Vinylene Transfer: Access to Unsubstituted Benzothiazines

Molecules, Год журнала: 2023, Номер 28(13), С. 5014 - 5014

Опубликована: Июнь 27, 2023

In this study, we report the synthesis of unsubstituted 1,2-benzothiazines through a redox-neutral Rh(III)-catalyzed C–H activation and [4+2]-annulation S–aryl sulfoximines with vinylene carbonate. Notably, introduction an N-protected amino acid ligand significantly enhances reaction rate. The key aspect process is utilization carbonate as oxidizing acetylene surrogate efficient transfer agent. This enables cyclization sulfoximine motifs, successfully forming diverse array 1,2-benzothiazine derivatives in moderate to good yields. Importantly, study highlights potential reactions for optically pure high enantiomeric purity.

Язык: Английский

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Rhodium-catalyzed divergent dehydroxylation/alkenylation of hydroxyisoindolinones with vinylene carbonate

Chemical Communications, Год журнала: 2023, Номер 59(98), С. 14559 - 14562

Опубликована: Янв. 1, 2023

A novel organic transformation involving rhodium-catalyzed divergent dehydroxylation/alkenylation of hydroxyisoindolinone with vinylene carbonate is reported, and the promising reagent presents a distinct chemical reactivity as vinyl-oxygen cyclic synthon.

Язык: Английский

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Rhodium(III)‐Catalyzed C−H/N−H Activation for Direct Synthesis of Pyrimidoindolones under Mild Conditions

Chemistry - An Asian Journal, Год журнала: 2023, Номер 18(19)

Опубликована: Авг. 24, 2023

Pyrimidoindolones are an important structural motif found in many natural products and essential to the pharmaceutical agrochemical industry. Direct synthesis of 3,4-unsubstituted pyrimidoindolones is not easily accessible. Here we report a rhodium(III)-catalyzed C-H/N-H activation annulation approach for obtaining from N-carbamoylindoles vinylene carbonate. The reaction occurs at room temperature does require any external oxidants. A diverse spectrum indoles were demonstrated be viable substrates capable producing desired high yields. In addition, scope has been expanded include pyrrole substrate. Furthermore, detailed mechanistic studies have performed delineate working mode reaction.

Язык: Английский

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Recent Progress in C—H Bond Activation Reaction with Vinylene Carbonate

Chinese Journal of Organic Chemistry, Год журнала: 2023, Номер 43(9), С. 3119 - 3119

Опубликована: Янв. 1, 2023

Язык: Английский

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Ruthenium‐catalyzed C−H Functionalization/Annulation ofN‐Aryl Indazoles/Phthalazines with Sulfoxonium Ylides to access Tetracyclic‐fused Cinnolines

Asian Journal of Organic Chemistry, Год журнала: 2022, Номер 11(8)

Опубликована: Июль 6, 2022

Abstract A ruthenium‐catalyzed cascade C−H functionalization/intramolecular annulation of N ‐phenylindazoles with sulfoxonium ylides was developed for the synthesis indazolo[1,2‐ a ]cinnolinones. This transformation features C−H/N−H functionalization in one pot , utilization cost‐effective ruthenium catalyst, wide substrate scope and good functional group tolerance. Moreover, reaction 2‐arylphthalazine‐1,4‐diones led to phthalazino[2,3‐ ]cinnolindiones under standard conditions.

Язык: Английский

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Recent Progress in Transition Metal-Catalyzed C—H Bond Activation of N-Aryl Phthalazinones

Chinese Journal of Organic Chemistry, Год журнала: 2022, Номер 42(9), С. 2682 - 2682

Опубликована: Янв. 1, 2022

Язык: Английский

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K2CO3-Promoted Formal [3+3]-Cycloaddition of N-Unsubstituted Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipoles with Knoevenagel Adducts

Molecules, Год журнала: 2023, Номер 28(3), С. 1034 - 1034

Опубликована: Янв. 19, 2023

The synthesis of dicyclic spiropyridazine oxoindole derivatives by using [3+3]-cycloaddition N-unsubstituted isatin N,N'-cyclic azomethine imine 1,3-dipoles was reported. products bearing two consecutive stereocenters, including spiroquaternary stereocenters in one ring structure, can be effectively obtained moderate to excellent yields (20-93%) and low diastereoselectivities (1:9-10:1 dr). synthesized compounds (>35 examples) were characterized single-crystal XRD, FTIR, NMR, mass spectral analysis.

Язык: Английский

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Rhodium-Catalyzed Direct Vinylene Annulation of 2-Aryloxazolines and Cascade Ring-Opening Using a Vinyl Selenone

Synlett, Год журнала: 2023, Номер unknown

Опубликована: Ноя. 20, 2023

Abstract Over the past two decades, transition-metal-catalyzed C–H activation and subsequent oxidative cyclization with alkynes or their surrogates has emerged as a powerful synthetic tool for fused heteroaromatics. We report Rh(III)-catalyzed annulation ring-opening cascade reaction 2-aryloxazolines. By utilizing vinyl selenone an oxidizing acetylene surrogate, target three-component coupling products were obtained in high yields without using stoichiometric amount of external oxidant.

Язык: Английский

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Synthesis of Fluoren‐9‐ones via Pd‐Catalyzed Annulation of 2‐Iodobiphenyls with Vinylene Carbonate

Chemistry - An Asian Journal, Год журнала: 2023, Номер 19(4)

Опубликована: Ноя. 29, 2023

Abstract A palladium‐catalyzed reaction for intermolecular selective C−H cyclocarbonylation of 2 ‐ iodobiphenyls is described. Intriguingly, the vinylene carbonate acts as a carbon monoxide transfer agent to enable annulation reaction. Moreover, versatile synthon, fluoren‐9‐one can be transformed into variety functionalized organic molecules, such [1,1′‐biphenyl]‐2‐carboxylic acid, 1′ H ,3′ ‐spiro[fluorene‐9,2′‐perimidine] and N ‐tosylhydrazones.

Язык: Английский

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Rh(III)‐Catalyzed C−H Annulation of 3‐Aryl‐2H‐benzo[e][1,2,4]thiadiazine‐1,1‐dioxides with Vinylene Carbonates

European Journal of Organic Chemistry, Год журнала: 2023, Номер 27(4)

Опубликована: Ноя. 22, 2023

Abstract A novel method has been developed for the synthesis of fused dihydroisoquinoline frameworks through a Rh(III)‐catalyzed annulation 3‐aryl‐2 H ‐benzo[ e ][1,2,4]thiadiazine‐1,1‐dioxides with vinylene carbonates by C−H bond activation. This is first report on oxidative functionalization aryl‐2 ][1,2,4]thiadiazine‐1,1‐dioxide carbonate to afford angularly heterocycles in good yields high functional group tolerance. In this approach, acts as glycolaldehyde surrogate construct ring systems.

Язык: Английский

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