Enantioselective Synthesis of Indole-Fused Polycycles Bearing Four Consecutive Stereocenters via Rhodium Catalysis

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 3, 2025

Indole-fused polycycles are common in natural products and bioactive molecules, yet their concise efficient synthesis remains challenging, especially for compounds with multiple stereocenters. Herein, we report the application of a chiral CpxRhIII catalyst enantioselective C–H activation/[4+2] annulation indoles bicyclic alkenes. This catalytic system exhibits high enantioselectivity broad functional group tolerance operates under benign conditions. The scope this methodology encompasses variety substrates, delivering novel polycyclic four consecutive stereocenters bridged ring good to excellent yields remarkable enantioselectivities (≤1:99 er). approach facilitates structurally diverse molecules that retain integrity while introducing chirality. More importantly, 3ab significantly inhibited proliferation CESS Kasumin-1 cells IC50 values 0.76 0.28 μM, respectively. In addition, has been demonstrated as an effective agent promoting apoptosis cells.

Язык: Английский

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Synthesis of CF3-Indazoles via Rh(III)-Catalyzed C-H [4+1] Annulation of Azobenzenes with CF3-Imidoyl Sulfoxonium Ylides

Molecules, Год журнала: 2025, Номер 30(1), С. 183 - 183

Опубликована: Янв. 5, 2025

An efficient Rh(III)-catalyzed C-H activation of azobenzenes and subsequent [4+1] cascade annulation with CF3-imidoyl sulfoxonium ylides was developed, yielding diverse CF3-indazoles. This protocol featured easily available starting materials, excellent functional group tolerance high efficiency. Moreover, the antitumor activities selected CF3-indazoles against human cancer cell lines were also studied, results indicated that several compounds displayed considerable antiproliferative activities.

Язык: Английский

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Novel Synthetic Method and Insecticidal Evaluation of CF₃-Containing Polycyclic Neonicotinoid Derivatives

Journal of Agricultural and Food Chemistry, Год журнала: 2025, Номер 73(9), С. 5033 - 5041

Опубликована: Фев. 22, 2025

The modification of active ingredients with a trifluoromethyl group represents significant approach for the discovery highly pesticides. Herein, we developed novel [3 + 3] annulation reaction neonicotinoid precursors and trifluoromethyl-α,β-ynones synthesized series CF3-containing polycyclic derivatives in high efficiency. insecticidal activity results indicated that most target compounds showed good activities against Aphis craccivora Nilaparvata lugens at concentration 100 mg/L. In particular, 3o 4k had LC50 values 1.53 1.47 mg/L A. craccivora, respectively, which were comparable to imidacloprid (LC50 = 1.30 mg/L). honeybee toxicity predictive model also potential low 4k. molecular docking study revealed exhibited favorable binding mode Lymnaea stagnalis acetylcholine-binding protein R55T-mutated resistant model.

Язык: Английский

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Unveiling the Synthesis of Indole-Fused Eight-Membered Aza-Heterocycles via FeCl₃–Catalyzed Radical C–N Coupling and Photophysical Studies

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 25, 2025

A novel strategy toward construction of indole-fused eight-membered heterocyclic rings through a radical pathway has been reported. Our approach involves tandem cyclization via FeCl3-catalyzed cross-dehydrogenative double C–N bond formation using DDQ as an oxidant under mild condition. An EPR experiment and time course 1H NMR study confirm that the addition triggers pyrazole N-radical, which contributes to eight-member framework with good yield. The structural diversity synthetic utility have explored, along photophysical properties synthesized compounds.

Язык: Английский

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Condition‐Controlled Selective Synthesis of CF₃‐Chromene and CF₃‐Benzofuran from N‐Phenoxyacetamide and CF₃‐Ynone

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 27, 2025

Comprehensive Summary Presented herein is a condition‐controlled selective synthesis of CF 3 ‐chromene and ‐benzofuran based on the reaction N ‐phenoxyacetamide ‐ynone. When carried out in MeOH under catalysis Rh(III), formed via C—H metalation‐initiated alkenylation, acetamide group migration intramolecular oxo ‐nucleophilic addition. On other hand, when run DMSO promotion CsOAc, generated aza ‐Michael addition‐initiated [3,3]‐σ rearrangement, addition water elimination. To our knowledge, this first report construction chromene or benzofuran scaffold along with introduction unit from same starting materials. The methodology was scalable products could be readily transformed into valuable products. Moreover, thus obtained possess decent anticancer activity.

Язык: Английский

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Modular Synthesis of gem-Difluorotetrahydrocarbazolone Scaffolds via Copper-Catalyzed Cascade Reaction of Bromodifluoroacetyl Indoles and Olefins

Organic Letters, Год журнала: 2024, Номер 26(42), С. 9085 - 9090

Опубликована: Окт. 16, 2024

A novel and efficient modular synthesis of

Язык: Английский

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