Recent Advances in Nucleophilic Lewis Base‐Catalyzed Cycloadditions for Synthesis of Spirooxindoles

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(24), С. 4412 - 4439

Опубликована: Ноя. 16, 2023

Abstract Spirooxindoles are privileged scaffolds in diverse bioactive natural products and pharmaceuticals, significant achievements for the construction of these molecules have thus been made past years. Among them, organocatalysis, particular, nucleophilic Lewis base catalysis, has recently emerged as an efficient reliable method preparation valuable functionalized spirooxindoles. According to different kinds catalysts, we summarize classify three catalytic strategies; tertiary amine‐catalyzed cycloadditions, NHC‐catalyzed phosphine‐catalyzed respectively. Through methods, potential spirooxindole skeletons owning various functional groups can be produced enrich small organic molecule library. In this review, describe a comprehensive updated advances cycloaddition reactions Meanwhile, related mechanism application annulation strategies product total synthesis will highlighted detail.

Язык: Английский

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Efficient construction of diverse spiro[indoline-3,4′-pyrrolo[3,4-b]pyridines] via [3 + 3] cycloaddition of MBH carbonates of isatins with β-enamino maleimides

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(35), С. 7099 - 7104

Опубликована: Янв. 1, 2022

An efficient method to construct unique spiro[indoline-3,4′-pyrrolo[3,4- b ]pyridines] was successfully developed via a DABCO promoted formal [3 + 3] cycloaddition reaction of MBH carbonates isatins with β-enamino maleimides under mild conditions.

Язык: Английский

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Rapid construction of S-containing spirooxindoles and dispirooxindoles via annulation of MBH maleimides of isatins

Tetrahedron Letters, Год журнала: 2025, Номер 156, С. 155452 - 155452

Опубликована: Янв. 13, 2025

Язык: Английский

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Selective construction of dispiro[indoline-3,2'-quinoline-3',3''-indoline] and dispiro[indoline-3,2'-pyrrole-3',3''-indoline] via three-component reaction

Beilstein Journal of Organic Chemistry, Год журнала: 2023, Номер 19, С. 1234 - 1242

Опубликована: Авг. 22, 2023

A convenient synthetic procedure for the construction of novel dispirooxindole motifs was successfully developed by base-promoted three-component reaction ammonium acetate, isatins and in situ-generated 3-isatyl-1,4-dicarbonyl compounds. The piperidine-promoted dimedone adducts 3-ethoxycarbonylmethyleneoxindoles afforded mutlifunctionalized dispiro[indoline-3,2'-quinoline-3',3''-indoline] derivatives good yields with high diastereoselectivity. On other hand, a similar 3-phenacylideneoxindoles unique dispiro[indoline-3,2'-pyrrole-3',3''-indoline] cyclohexanedione substituent. plausible mechanism is proposed to explain formation different spirooxindoles.

Язык: Английский

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The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition

Beilstein Journal of Organic Chemistry, Год журнала: 2023, Номер 19, С. 982 - 990

Опубликована: Июнь 29, 2023

The three-component reaction of isoquinolines, dialkyl acetylenedicarboxylates, and 5,6-unsubstituted 1,4-dihydropyridines in acetonitrile at room temperature afforded functionalized isoquinolino[1,2-f][1,6]naphthyridines good yields with high diastereoselectivity. More importantly, the formal [2 + 2] cycloaddition acetylenedicarboxylates refluxing gave unique 2-azabicyclo[4.2.0]octa-3,7-dienes as major products 1,3a,4,6a-tetrahydrocyclopenta[b]pyrroles minor via further rearrangement.

Язык: Английский

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Synthesis of novel organophosphorus compounds via reaction of substituted 2-oxoindoline-3-ylidene with acetylenic diesters and triphenylphosphine or triphenyl phosphite

Scientific Reports, Год журнала: 2024, Номер 14(1)

Опубликована: Март 15, 2024

Abstract An efficient reaction between triphenylphosphine or triphenyl phosphite and 2-oxoindoline-3-ylidene derivatives in the presence of acetylenic esters leads to functionalized containing phosphorus ylieds phosphonate esters. All compounds obtained these reactions are stable have good yields.

Язык: Английский

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