Copper-Catalyzed [3 + 2] Annulation of O-Acyl Oximes with p-Hydroquinones for the Synthesis of 5-Hydroxyindoles

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 4, 2024

A copper-catalyzed [3 + 2] annulation of

Язык: Английский

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Five-membered ring systems: Furans and benzofurans

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 175 - 209

Опубликована: Янв. 1, 2024

Язык: Английский

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Cobalt‐Catalyzed Annulation of o‐Phenylenediamines and Internal Alkynes: Efficient Synthesis of Quinoxaline Derivatives

European Journal of Organic Chemistry, Год журнала: 2023, Номер 27(3)

Опубликована: Ноя. 6, 2023

Abstract A cobalt‐catalyzed annulation of o ‐phenylenediamines and internal alkynes for the synthesis quinoxalines is developed. This method provides a variety in good to high yields under simple mild reaction conditions with molecular O 2 as terminal oxidant. Preliminary mechanistic studies show that novel mechanism involved current reaction, which different from previous reported dicarbonyl compound via oxidation alkyne.

Язык: Английский

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Copper-mediated [3 + 2] oxidative cyclization of oxime acetate and its utility in the formal synthesis of fentiazac

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 22(3), С. 521 - 528

Опубликована: Дек. 1, 2023

A new protocol for the direct synthesis of 2-aminothiazole has been developed from oxime acetate and readily available sodium thiocyanate using a copper catalyst. The present transformation good functional group tolerance. Various thiazoles were smoothly synthesized in to excellent yields. applicability method extended formal non-steroidal anti-inflammatory drug, fentiazac

Язык: Английский

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Generation and Radical-Radical Cross-Coupling of Alkenyloxy Radical: Ester and Ketone Synthesis

Опубликована: Янв. 1, 2024

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Язык: Английский

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Deconstructive diversification of cyclic 1,3-diketones for accessing hydrazonylated 1,n-ketoesters

Tetrahedron, Год журнала: 2024, Номер 153, С. 133855 - 133855

Опубликована: Янв. 26, 2024

Язык: Английский

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Iron-Catalyzed Oxidative C(sp3)–C(sp3) Radical Coupling Reaction between Thiohydantoins and O-Acetyloximes for the Synthesis of 1,3-Dibenzyl-3,4-dihydropyrrolo[2,3-d]imidazole-2(1H)-thione Derivatives

Synlett, Год журнала: 2024, Номер unknown

Опубликована: Апрель 9, 2024

Abstract A unified heteroannelation method to achieve the synthesis of 1,3-dibenzyl-3,4-dihydropyrrolo[2,3-d]imidazole-2(1H)-thione derivatives with an iron catalyst is proposed. The annelation reaction follows a C(sp3)–C(sp3) radical coupling between thiohydantoin and O-acetyloxime. synthetic approach enables access several alkynylated thiohydantoins O-acetyloximes controlled selectivity toward rather than C(sp3)–C(sp3)–O in moderate high yields. An optimization study has been carried out by changing loading, oxidants, solvents, temperature. Synthesized compounds were characterized through 1H 13C NMR mass spectral studies.

Язык: Английский

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Synthesis of 2H-imidazoles via Copper-Catalyzed Homo/Cross-Coupling of Oxime Acetates

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(36), С. 7316 - 7320

Опубликована: Янв. 1, 2024

A facile and practical protocol to construct 2 H -imidazoles by applying an oxime acetate block as the sole component via homo/cross-coupling catalyzed Cu( i ) was developed.

Язык: Английский

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Synthesis of furoquinolinones/pyranones/coumarins via a copper-catalyzed heteroannulation of oxime acetates and 1,3-cyclic dicarbonyls

Tetrahedron, Год журнала: 2024, Номер 166, С. 134212 - 134212

Опубликована: Авг. 26, 2024

A divergent copper-mediated cyclization between oxime acetates and distinct 1,3-cyclic dicarbonyl compounds such as 4-hydroxyquinolinones/pyranones/coumarins was developed. Using the same reaction conditions, an array of furan-fused heterocycles furoquinolinones/pyranones/coumarins were prepared in good to high yields. The products possess a less common substitution pattern than those previous syntheses. mildness protocol enables broad scope without affecting sensitive functionalities azido, alcohol, terminal alkyne, alkyl ester, halide groups. Mechanistic investigations infer purely organometallic pathway, excluding participation radical intermediates. Ultimately, heteroannulation exploited key step short high-yielding synthesis phytoestrogen coumestrol.

Язык: Английский

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Five-membered ring systems: Pyrroles and benzo analogs

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 123 - 173

Опубликована: Янв. 1, 2024

Язык: Английский

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