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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Convenient Synthetic Protocols for Diverse Functionalized Dihydrobenzofuran-Fused Spiro-indanedione-oxindole Scaffolds

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(16), С. 11562 - 11580

Опубликована: Июль 27, 2023

Diverse functionalized dihydrobenzofuran spiro-indanedione-oxindole scaffolds were conveniently synthesized by base-promoted cyclization reaction of Morita-Baylis-Hillman (MBH) carbonates isatins and 2-(o-hydroxybenzylidene)-1,3-indanediones. The two diastereomeric dispiro[indene-2,1'-cyclopenta[b]benzofuran-2',3″'-indolines] could be selectively using DABCO or DMAP as a base promoter. More importantly, facilitated the annulation MBH formates 2-(o-hydroxybenzylidene)-1,3-indanediones selectively, resulting in spiro[cyclopropa[c]chromene-1,2'-indene]-1',3'-diones dispiro[indene-2,1'-cyclopenta[b]benzofuran-2',3″'-indolines]. Additionally, similar with maleimides afforded dispiro[indene-2,5'-benzofuro[2',3':1,5]cyclopenta[1,2-c]pyrrole-4',3″'-indolines] high yields diastereoselectivity.

Язык: Английский

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A review on DBU-mediated organic transformations

Green Chemistry Letters and Reviews, Год журнала: 2022, Номер 15(3), С. 765 - 795

Опубликована: Июль 3, 2022

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) has received a significant importance in organic synthesis during recent years because of its interesting ability to catalyze reaction sufficiently at mild conditions. DBU can work as catalyst under simple conditions inducing the operational simplicity experimental procedures by reducing side products and waste. The notable advantages these cases include less expensive which is commercially readily available, easy handle, most importantly recoverable. been explored for several practical methodologies highly useful wide variety materials. selectivity (chemo-, regio-, stereo-) reactions impressive applicable modern chemical transformations. possesses enhanced basic properties high mechanical well thermal stability. In years, large number transformations have carried out using catalyst. successfully employed conduct including usual modifications, cyclizations, eliminations, esterifications, condensation reactions, multicomponent etc. fact, last few decades, tremendous interest sparked various promoted publications appeared literature. Since catalyzed recently proven be important we review this article protocols

Язык: Английский

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An Access to Highly Functionalized Dihydrobenzofuran Spirooxindole Scaffolds

Organic Letters, Год журнала: 2022, Номер 24(42), С. 7790 - 7795

Опубликована: Окт. 14, 2022

We have developed an efficient protocol for the construction of polycyclic dihydrobenzofuran spirooxindole scaffolds via base promoted cascade annulation Morita-Baylis-Hillman (MBH) carbonates isatins with ortho-hydroxychalcones or ortho-hydroxy-β-nitrostyrenes. The complex compounds were conveniently synthesized in satisfactory yields and high diastereoselectivity. This provides a swift convenient approach assembly diverse highly functionalized spirooxindoles also features broad substrate scope, molecular convergence, excellent atomic economy.

Язык: Английский

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Cooperative photoactivation/Lewis base catalyzed [4 + 2] annulations of α-diazoketones andortho-amino MBH carbonates to access dihydroquinolinone frameworks

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(4), С. 1034 - 1041

Опубликована: Янв. 1, 2023

A series of dihydroquinolinones have been synthesized via synergistic catalysis combining photolysis and Lewis base utilizing in situ generated ketenes ortho -amino MBH carbonates.

Язык: Английский

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Modular Assembly of Six‐Membered Carbocyclic Spirooxindoles via Peterson Olefination/Michael Addition/C(sp³) Arylation Cascade

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(21), С. 2614 - 2620

Опубликована: Июль 3, 2024

Comprehensive Summary Concise assembly of spirooxindoles is great significance but a challenging task in modern organic synthesis. Described herein an unusual base‐promoted [4+2] spiroannulation rarely used isatin‐derived β‐silylcarbinols with o ‐halogen aromatic ketones, which enables rapid and modular synthesis six‐membered carbocyclic high yields excellent functional group tolerance (> 50 examples). Mechanistic experiments revealed that this reaction involved Peterson olefination, Michael addition intramolecular C(sp 3 ) arylation cascade. The variegated synthetic derivatization target products successful construction bioactive molecules further illustrate the potential spirooxindole‐related drug discovery.

Язык: Английский

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Synthesis of 1,3,5-trisubstituted pyrazolesvia1,3-dipolar cycloaddition of nitrile imines with ninhydrin-derived Morita–Baylis–Hillman carbonates

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(34), С. 6923 - 6930

Опубликована: Янв. 1, 2022

An effective method for 1,3,5-trisubstituted pyrazoles via 1,3-dipolar cycloaddition reaction from ninhydrin-derived Morita–Baylis–Hillman carbonates and nitrilimines has been developed.

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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Direct access to spirooxindole dihydropyrrole fused pyrazolones and bis-spiropyrazolone derivatives

Tetrahedron Letters, Год журнала: 2022, Номер 97, С. 153791 - 153791

Опубликована: Апрель 14, 2022

Язык: Английский

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COAP-Pd Catalyzed Asymmetric Allylic Alkylation of Azlactones with MBH Carbonates: Access to Unnatural α-Quaternary Stereogenic Glutamic Acid Derivatives

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(16), С. 11867 - 11873

Опубликована: Авг. 1, 2023

A palladium-catalyzed regioselective and asymmetric allylic alkylation of azlactones with MBH carbonates has been developed chiral oxalamide-phosphine ligands. The corresponding reaction afforded a range optically active γ-arylidenyl glutamic acid derivatives bearing an α-chiral quaternary stereocenter in good yields excellent linear regio- high enantioselectivity. This protocol furnishes alternative approach for the construction enantio-enriched unnatural α-amino derivatives.

Язык: Английский

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