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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An update on the progress of cycloaddition reactions of 3-methyleneindolinones in the past decade: versatile approaches to spirooxindoles

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(36), С. 7768 - 7791

Опубликована: Янв. 1, 2021

This review focuses on important cycloaddition reactions of 3-methyleneindolinones to afford 3,3′-spirocyclic oxindoles.

Язык: Английский

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Recent synthetic strategies toward the synthesis of spirocyclic compounds comprising six-membered carbocyclic/heterocyclic ring systems

Molecular Diversity, Год журнала: 2020, Номер 25(4), С. 2487 - 2532

Опубликована: Июль 21, 2020

Язык: Английский

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Recent approaches to the synthesis of tetrahydrocarbazoles

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(9), С. 1926 - 1939

Опубликована: Янв. 1, 2021

The tetrahydrocarbazole (THC) motif is ubiquitous in natural products and biologically active compounds. THCs can serve as favorable synthetic intermediates or precursors en-route to desired complex products. Despite a considerable number of strategies for the synthesis that have emerged last two decades, only handful reviews been published on subject. Herein, we summarized methodologies ten years benefit organic chemists. review focuses non-enantioselective syntheses THCs, encompasses ring opening reactions donor-acceptor cyclopropanes, metal-catalyzed C-C/C-N bond formation, cycloaddition, conjugate addition, miscellaneous employed accessing THC framework.

Язык: Английский

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Acid-Modulated Construction of Cyclopenta[b]indole and Cyclohepta[b]indole via Unprecedented C3/C2 Carbocation Rearrangement

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(9), С. 5440 - 5456

Опубликована: Апрель 3, 2023

p-TsOH-catalyzed cycloaddition of various 3-vinylindoles and (indol-2-yl)diphenylmethanols in acetonitrile gave the functionalized cyclopenta[b]indoles good yields with high diastereoselectivity via [3 + 2] reaction. More importantly, FeCl3-catalyzed annulation reaction afforded unexpected cyclohepta[1,2-b:4,5-b']diindoles satisfactory yields, which a formal [4 3] an unprecedented C3/C2 carbocation rearrangement were first confirmed by determination single-crystal structure.

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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Annulations involving 2-arylidene-1,3-indanediones: stereoselective synthesis of spiro- and fused scaffolds

New Journal of Chemistry, Год журнала: 2020, Номер 44(40), С. 17148 - 17176

Опубликована: Янв. 1, 2020

Stereoselective annulations of 2-arylidene-1,3-indanediones towards spiro-carbocycles as well spiro/fused heterocycles based on various cycloadditions and tandem are described.

Язык: Английский

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Diastereoselective Synthesis of Tetrahydrospiro[carbazole-1,3′-indolines] via an InBr₃-Catalyzed Domino Diels–Alder Reaction

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(8), С. 5616 - 5629

Опубликована: Апрель 5, 2021

A simple InBr3-catalyzed domino reaction of indoles, phenylacetylenes, and various 3-methyleneoxindolines in toluene is described. This not only provided a convenient synthetic protocol for polysubstituted tetrahydrospiro[carbazole-1,3′-indolines] good yields but also gave completely different diastereoisomers the to that previously reported TfOH-catalyzed one-pot acetophenones, 3-methyleneoxindolines. Additionally, initially prepared 1,1′-bis(indolyl)phenylethanes with 3-phenacylideneoxindolines corresponding excellent diastereoselectivity. The mechanism involved sequential situ generation reactive dienophilic 3-alkenylindole, Diels–Alder reaction, Lewis acid controlled diastereoisomerization process.

Язык: Английский

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Diastereoselective synthesis of spiro[chromane-3,3′-indolines] and spiro[chromane-3,2′-indenes] via DBU promoted formal [4 + 2]cycloaddition reaction

Green Synthesis and Catalysis, Год журнала: 2021, Номер 3(1), С. 53 - 58

Опубликована: Окт. 22, 2021

A new DBU-catalyzed formal [4 ​+ ​2] cycloaddition between ortho-hydroxyphenyl-substituted para-quinone methides and electron-deficient dienophiles including 3-methyleneoxindoles 2-aryldeneindene-1,3-diones was established. wide range of functionalized spiro[chromane-3,3′-indolines] spiro[chromane-3,2′-indenes] were successfully synthesized in good yields with high diastereoselectivity. The features the reaction included readily available substrates, mild conditions, convenient methodology functional group tolerance.

Язык: Английский

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Efficient construction of diverse spiro[indoline-3,4′-pyrrolo[3,4-b]pyridines] via [3 + 3] cycloaddition of MBH carbonates of isatins with β-enamino maleimides

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(35), С. 7099 - 7104

Опубликована: Янв. 1, 2022

An efficient method to construct unique spiro[indoline-3,4′-pyrrolo[3,4- b ]pyridines] was successfully developed via a DABCO promoted formal [3 + 3] cycloaddition reaction of MBH carbonates isatins with β-enamino maleimides under mild conditions.

Язык: Английский

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