Three-Component Reaction for the Synthesis of Spiro-Heterocycles from Isatins, Substituted Ureas, and Cyclic Ketones

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(5), С. 3441 - 3452

Опубликована: Фев. 20, 2024

We reported an efficient three-component reaction to access new spiro heterocycles through the annulation reactions of isatins, substituted ureas, and cyclic ketones under normal laboratory conditions, which is another example isatins being used build compounds by ring-opening recyclization processes. The wide range substrates, simple operation, experimental high yields make approach practical value.

Язык: Английский

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Regioselective and Diastereoselective Construction of Diverse Dispiro-Indanone-Fluorenone-Oxindole Motifs

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(24), С. 17181 - 17196

Опубликована: Ноя. 28, 2023

A convenient synthetic protocol for regioselective and diastereoselective construction of complex dispiro-indanone-fluorenone-oxindole motifs was developed by the base-promoted annulation reaction bindone MBH carbonates isatins adjusting conditions. DABCO promoted in DCM at room temperature, affording dispiro[indene-2,4′-fluorene-1′,3″-indoline] derivatives good yields with high diastereoselectivity. Triethylamine two molecular 1,3-indanediones esters ethanol elevated temperature selectively gave dispiro[indene-2,4′-fluorene-3′,3″-indolines] moderate yields. However, triethylamine excess refluxing ethanol, Z-isomer as major product E-isomer minor product.

Язык: Английский

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Recent applications of 1,3-indanedione in organic transformations for the construction of fused- and spiro scaffolds

Tetrahedron, Год журнала: 2022, Номер 122, С. 132954 - 132954

Опубликована: Авг. 9, 2022

Язык: Английский

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Molecular Diversity of Base Promoted Annulation of MBH Carbonates of Isatins and Dialkyl But‐2‐ynedioates

ChemistrySelect, Год журнала: 2023, Номер 8(39)

Опубликована: Окт. 19, 2023

Abstract DABCO promoted one‐pot three‐component reaction of aromatic amines, dialkyl but‐2‐ynedioates and MBH nitriles isatins selectively afforded two diastereomeric spiro[indoline‐3,4′‐pyridines] in comparable yields. On the other hand, cyclization carbonates DCM at room temperature gave spiro[cyclopentane‐1,3′‐indoline] derivatives, while chloroform 70 °C resulted unique cyclopenta[ c ]quinolone derivatives with ring‐opening isatin moiety. A plausible mechanism was rationally proposed to explain formation different products.

Язык: Английский

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Construction of Spiro[benzo[a]acridine-12,4′-imidazolidine]-2′,5′-dione Derivatives via Ring-Opening and Recyclization of Isatins and C–OH Cleavage of 2-Naphthol

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(11), С. 6995 - 7005

Опубликована: Май 8, 2023

An efficient three-component reaction to access spiro[benzo[a]acridine-12,4'-imidazolidine]-2',5'-dione derivatives has been developed through the ring-opening and recyclization process of isatins dehydroxylation 2-naphthol, which is different from their conventional modes. Experimental observations suggest that p-toluenesulfonic acid key factor promotes success this synthetic strategy. The research provided a novel approach for construction spiro compounds 2-naphthol in organic synthesis.

Язык: Английский

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Molecular diversity of the acid promoted domino reaction of 3-hydroxy-3-(indol-3-yl)indolin-2-ones and cyclic mercapto-substituted β-enamino esters

New Journal of Chemistry, Год журнала: 2021, Номер 45(18), С. 8314 - 8320

Опубликована: Янв. 1, 2021

The acetic acid promoted reaction of 3-hydroxy-3-(indol-3-yl)indolin-2-ones and mercapto-substituted β-enamino esters showed very interesting molecular diversity.

Язык: Английский

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Recent Progress in the Synthesis of Heterocycles based on 1,3-diketones

Current Organic Synthesis, Год журнала: 2021, Номер 19(2), С. 220 - 245

Опубликована: Окт. 12, 2021

N,O-heterocycles containing the dicarbonyl ring play a significant role in heterocyclic and therapeutic chemistry. Since discovery of 1,3-diketones, numerous research works have been achieved regarding synthesis its chemical reactivity. In this review, we described most relevant publications involving β-diketone compounds published during period between 2018 to date. addition, include 1,3-diketones-based prepared by various synthetic methodologies.

Язык: Английский

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Synthesis of acyloxy-2H-azirine and sulfonyloxy-2H-azirine derivatives via a one-pot reaction of β-enamino esters, PIDA and carboxylic acid or sulfonic acid

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(15), С. 3061 - 3066

Опубликована: Янв. 1, 2022

PIDA mediated oxidative acyloxylation/azirination and sulfonyloxylation/azirination of β-enamino esters were investigated.

Язык: Английский

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Six-membered ring systems: with O and/or S atoms

Progress in heterocyclic chemistry, Год журнала: 2021, Номер unknown, С. 473 - 532

Опубликована: Янв. 1, 2021

Язык: Английский

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Heterocycles as Inputs in MCRs : An Update

Опубликована: Ноя. 26, 2021

Multicomponent reactions have great impact on modern organic synthesis. However, the use of heterocycles as reactants in these processes is less developed. In this review, role representative inputs multicomponent updated. We classify recent results area according to main reactivity mode involved transformation: concerted, radical, metal-catalyzed, carbonyl/imine, and isocyanide-based processes. Some applications are also commented.

Язык: Английский

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