Stereoselective synthesis and applications of spirocyclic oxindoles

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(5), P. 1026 - 1084

Published: Jan. 1, 2021

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

Language: Английский

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Expeditious entry into carbocyclic and heterocyclic spirooxindoles

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(29), P. 5651 - 5693

Published: Jan. 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.

Language: Английский

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Recent advances in the applications of pyrazolone derivatives in enantioselective synthesis

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(12), P. 2370 - 2386

Published: Jan. 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.

Language: 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, Journal Year: 2022, Volume and Issue: 10(2), P. 540 - 547

Published: Dec. 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.

Language: 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, Journal Year: 2020, Volume and Issue: 56(73), P. 10718 - 10721

Published: Jan. 1, 2020

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

Language: 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, Journal Year: 2022, Volume and Issue: 87(5), P. 3184 - 3194

Published: Feb. 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.

Language: Английский

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

Coordination Chemistry Reviews, Journal Year: 2023, Volume and Issue: 501, P. 215562 - 215562

Published: Nov. 27, 2023

Language: Английский

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Convenient synthesis of chromene-fused spirocyclopentane-1,2-dioxindoles via base promoted annulation reaction

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: 156, P. 155455 - 155455

Published: Jan. 8, 2025

Language: Английский

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

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: 156, P. 155452 - 155452

Published: Jan. 13, 2025

Language: Английский

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Molecular diversity of the reactions of MBH carbonates of isatins and various nucleophiles

Beilstein Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 21, P. 286 - 295

Published: Feb. 6, 2025

In this paper, the nucleophilic substitution reactions of various N- and P-containing nucleophiles to MBH carbonates isatins were investigated. Diverse functionalized 3-substituted oxindole derivatives successfully prepared in satisfactory yields with high diastereoselectivity. addition, base-promoted dimerization isatin afforded ethylene-bridged bis(3-methylene)oxindole nearly 4:1 diastereomeric ratios. The relative configurations polycyclic compounds clearly elucidated by determination several single crystal structures.

Language: Английский

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