Stereoselective synthesis and applications of spirocyclic oxindoles

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(5), С. 1026 - 1084

Опубликована: Янв. 1, 2021

This review summaries recent synthetic developments towards spirocyclic oxindoles and applications as valuable medicinal targets.

Язык: Английский

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Expeditious entry into carbocyclic and heterocyclic spirooxindoles

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(29), С. 5651 - 5693

Опубликована: Янв. 1, 2022

Recent advances in the chemistry of base-, metal-, nano-metal and organo-catalyst mediated achiral chiral versions structurally diverse pharmaceutically relevant spirooxindoles are gently reviewed.

Язык: Английский

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Recent advances in the applications of pyrazolone derivatives in enantioselective synthesis

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(12), С. 2370 - 2386

Опубликована: Янв. 1, 2022

Pyrazolones and pyrazoles, featuring nitrogen-nitrogen bonds, are two of the most important classes heterocycles, owing to their widespread occurrence in medicinal chemistry functional materials. The last decade has witnessed a rapid increase construction chiral pyrazolone pyrazole derivatives, with application derivatives as powerful synthons. Since our review 2018, large number new achievements emerged this area, requiring timely update. Thus, summarizes these elegant based on multiple reactive sites different In addition, mechanisms interesting biological investigations relating corresponding products also discussed.

Язык: Английский

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Selective construction of spiro[indoline-3,5′-pyrrolo[3,4-b]azepines] and spiro[indoline-3,3′-pyrroles] via a [4 + 3]/[3 + 2] cycloaddition reaction of α,β-unsaturated aldimines and MBH adducts of isatins

Organic Chemistry Frontiers, Год журнала: 2022, Номер 10(2), С. 540 - 547

Опубликована: Дек. 10, 2022

An efficient synthetic protocol for the selective construction of spiro[indoline-3,5′-pyrrolo[3,4- b ]azepines] and spiro[indoline-3,3′-pyrroles] via a cycloaddition reaction α,β-unsaturated aldimines MBH adducts isatins was successfully developed.

Язык: Английский

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Enantioselective [3+2] annulation of isatin-derived MBH-carbonates and 3-nitroindoles enabled by a bifunctional DMAP-thiourea

Chemical Communications, Год журнала: 2020, Номер 56(73), С. 10718 - 10721

Опубликована: Янв. 1, 2020

Highly enantioselective [3+2] annulation of isatin-derived MBH-carbonates and 3-nitroindoles was achieved by a chiral DMAP-thiourea bifunctional catalyst.

Язык: Английский

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Organocatalytic Regio- and Enantioselective [3 + 2]-Annulations of Ninhydrin-Derived Morita–Baylis–Hillman Carbonates with 3-Methyleneoxindoles

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(5), С. 3184 - 3194

Опубликована: Фев. 8, 2022

A type of Morita-Baylis-Hillman (MBH) carbonates has been developed from ninhydrin. These MBH have successfully employed as 3C-synthons in the organocatalytic asymmetric [3 + 2]-annulations isatin-derived electron-deficient olefins, affording structurally diverse spirooxindoles high yield with excellent stereoselectivity. In particular, regioselectivity was controlled by reaction partner, 3-methyleneoxindoles carbonyl groups (R = ArCO), β-selective products and ester CO2Me) furnishing γ-selective products. The representative scale-up reactions transformation product were examined. mechanism expounded control experiments.

Язык: Английский

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Recent advances in the development of fluorescent probes for γ‐glutamyltranspeptidase

Coordination Chemistry Reviews, Год журнала: 2023, Номер 501, С. 215562 - 215562

Опубликована: Ноя. 27, 2023

Язык: Английский

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Recent Advances in Catalytic Enantioselective Synthesis of Pyrazolones with a Tetrasubstituted Stereogenic Center at the 4-Position

Synthesis, Год журнала: 2020, Номер 53(02), С. 215 - 237

Опубликована: Окт. 8, 2020

Abstract Pyrazolone [2,4-dihydro-3H-pyrazol-4-one] represents one of the most important five-membered nitrogen heterocycles which is present in numerous pharmaceutical drugs and molecules with biological activity. Recently, many catalytic methodologies for asymmetric synthesis chiral pyrazolones have been established great success, specially, bearing a tetrasubstituted stereocenter at C-4. This review summarizes these excellent research studies since 2018, including representative examples some mechanistic pathways explaining observed stereochemistry. 1 Introduction 2 Catalytic Enantioselective Synthesis Chiral Pyrazolones Full Carbon Tetrasubstituted Stereocenter C-4 3 Quaternary Heteroatom 4 Spiropyrazolones 5 Conclusion

Язык: Английский

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Diastereoselective synthesis of dispiro[indoline-3,3′-furan-2′,3′′-pyrrolidine] via [3 + 2]cycloaddition reaction of MBH maleimides of isatins and 1,3-dicarbonyl compounds

Organic Chemistry Frontiers, Год журнала: 2020, Номер 7(20), С. 3202 - 3208

Опубликована: Янв. 1, 2020

In the presence of mixed bases DABCO and K₂CO₃, reaction MBH maleimides isatins with various cyclic 1,3-dicarbonyl compounds afforded functionalized dispiro[indoline-3,3′-furan-2′,3′′-pyrrolidines] in satisfactory yields high diastereoselectivity.

Язык: Английский

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Enantioselective Synthesis of Spirooxindole‐pyran and furan Scaffolds via Copper‐Catalyzed Formal (3+3) and (3+2) Cycloaddition of Isatin‐derived Propargylic Esters

Chemistry - A European Journal, Год журнала: 2024, Номер 31(8)

Опубликована: Дек. 12, 2024

Herein, we report a copper-catalyzed enantioselective formal (3+3) and (3+2) cycloaddition reaction of isatin-derived tertiary propargylic esters with N,N-dimethylbarbituric acid 4-hydroxycoumarins, respectively. In this process, the ester serves as both C3- C2-synthons, facilitating synthesis optically active spirooxindole-pyran furan scaffolds featuring an all-carbon quaternary stereocenter. The delivers these spirocyclic frameworks in good yields high enantioselectivities. Additionally, scalability reactions transformation chiral intermediates into valuable structures emphasize synthetic practical importance strategy.

Язык: Английский

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