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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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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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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Synthesis spiro and fused chromenes via [4 + 2] cycloaddition of salicyl N-tosylimines and cyclic dienophiles

Journal of Molecular Structure, Год журнала: 2024, Номер 1304, С. 137684 - 137684

Опубликована: Фев. 4, 2024

Язык: Английский

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Construction of Cyclopentanes Consisting of Five Stereocenters via NHC-Catalyzed Cascade Reactions of Enals with Oxindole-Dienones

Organic Letters, Год журнала: 2023, Номер 25(47), С. 8445 - 8450

Опубликована: Ноя. 17, 2023

Despite the widespread presence of chiral cyclopentane motif, asymmetric synthesis cyclopentanes containing five stereocenters remains a formidable challenge. Here, we present an N-heterocyclic carbene (NHC)-catalyzed cascade reaction enal and oxindole-dienone, which allows access to spiroxindole featuring complete set centers on five-membered carbocycle. This strategy, characterized by formation multiple bonds centers, demonstrates broad substrate scope, exclusive diastereoselectivity, up 99:1 er.

Язык: Английский

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Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(15), С. 10854 - 10866

Опубликована: Июль 12, 2024

A convenient synthetic protocol for diverse fused chromenes was successfully developed by a three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and various cyclic 1,3-dipolarophiles containing

Язык: Английский

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Base-Mediated Annulation of ortho-Iminophenols and ortho-Vinylphenols with MBH Carbonates of Isatins: Straightforward Access to Dihydrobenzofuran and Benzofuran Derivatives

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(21), С. 15472 - 15489

Опубликована: Окт. 15, 2024

We have developed a convenient synthetic protocol for efficient construction of significant dihydrobenzofuran and benzofuran scaffolds by Lewis base-mediated annulation reaction ortho-iminophenols ortho-vinylphenols with MBH carbonates isatins under mild metal-free conditions. The selective generation different kinds derivatives was successfully achieved employing substituted isatin-derived ortho-N-tosyliminophenols ortho-vinylphenols. features included broad substrate scopes, excellent functional group compatibility, high molecular diversity, atomic economy.

Язык: Английский

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Tandem ring-opening and formal [3 + 2] cycloaddition of furo[2,3-d]pyrimidine-2,4-diones

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(29), С. 6028 - 6033

Опубликована: Янв. 1, 2023

The base promoted tandem annulation reaction of activated cyclic 1,3-dipolarophiles such as 2-arylidene-1,3-indanediones, 2-(o-hydroxybenzylidene)-1,3-indanediones and 3-methyleneoxindoles with functionalized furo[2,3-d]pyrimidine-2,4-diones was systematically investigated. This provided efficient synthetic protocols for complex dispiro/dispiro fused tricyclic compounds including dispiro[indene-2,3'-cyclopentane-1',5''-pyrimidines], dispiro[indoline-3,3'-cyclopentane-1',5''-pyrimidines] spiro[cyclopenta[c]indeno[1,2-b]chromene-3,5'-pyrimidines] in good yields high diastereoselectivity. believed to proceed via sequential ring-opening the furyl ring, formal [3 + 2] cycloaddition o-hydroxyphenyl group.

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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Enantioselective Synthesis of Spiro[cyclopentane-1,3′-oxindole] Scaffolds with Five Consecutive Stereocenters

Organic Letters, Год журнала: 2024, Номер 26(30), С. 6402 - 6406

Опубликована: Июль 22, 2024

A highly diastereo- and enantioselective cascade annulation reaction of Morita-Baylis-Hillman (MBH) maleimides isatins with

Язык: Английский

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