Synthesis of Spiro[indoline-pyridine]-dicarboxylates and Substituted Alkylidene Oxindoles by Azomethine Ylides and MBH Carbonates of Isatins

Organic Letters, Год журнала: 2024, Номер 26(19), С. 4117 - 4121

Опубликована: Май 9, 2024

We have developed an efficient protocol for the synthesis of spiro[indoline-pyridine]dicarboxylates and substituted alkylidene oxindoles through [3 + 3] cycloaddition Michael addition individually by azomethine ylides various MBH carbonates isatins. The selective generation cyclic products chain was achieved changing substituents at 3-position oxindoles. features this method include convenient catalysts, mild reaction conditions, broad substrate scopes.

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 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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Rapid construction of tricyclic tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine via isocyanide-based multicomponent reaction

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 1436 - 1443

Опубликована: Июнь 28, 2024

An efficient protocol for the synthesis of polyfunctionalized tetrahydrocyclopenta[4,5]pyrrolo[2,3- b ]pyridine-3,4b,5,6,7(1 H )-pentacarboxylates was developed by a three-component reaction. In absence any catalyst, reaction alkyl isocyanides, dialkyl but-2-ynedioates and 5,6-unsubstituted 1,4-dihydropyridines in refluxing acetonitrile afforded high yields with diastereoselectivity. The finished situ generation activated 5-(alkylimino)cyclopenta-1,3-dienes from addition isocyanide to two molecules sequential formal [3 + 2] cycloaddition 1,4-dihydropyridine.

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

Tetrahedron Letters, Год журнала: 2025, Номер 156, С. 155455 - 155455

Опубликована: Янв. 8, 2025

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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Construction of Spiro[indoline‐3,2′‐pyrrolo[2,1‐a]Isoquinoline] and Spiro[indoline‐3,2′‐pyrrolo[1,2‐a]Quinoline] via Isocyanide‐Based Three‐Component Reaction

ChemistrySelect, Год журнала: 2025, Номер 10(4)

Опубликована: Янв. 1, 2025

Abstract A convenient synthetic protocol for novel spiro[indoline‐3,2′‐pyrrolo[2,1‐ a ]isoquinoline] and spiro[indoline‐3,2′‐pyrrolo[1,2‐ ]quinoline] motifs was successfully developed by three‐component reaction of isoquinoline (quinoline), cyclohexyl isocyanide, isatylidene malononitriles. In the absence any catalyst, isoquinoline, malononitriles in refluxing dichloromethane gave functionalized ]isoquinolines] good yields with high diastereoselectivity. However, similar quinoline afforded ]quinolines] about 2:1

Язык: Английский

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

Beilstein Journal of Organic Chemistry, Год журнала: 2025, Номер 21, С. 286 - 295

Опубликована: Фев. 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.

Язык: Английский

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