Silver-Enabled Dearomative Trifluoromethoxylation of Indoles

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(4), С. 2325 - 2332

Опубликована: Янв. 17, 2024

The only known method for the dearomative trifluoromethoxylation of indoles is preliminary, with one substrate successfully undergoing reaction. In this study, we not developed a broadly applicable indole but also achieved divergent by fine-tuning reaction conditions. Under optimized conditions, silver salt and an easily handled OCF3 reagent, various smoothly underwent dearomatization to afford diverse array ditrifluoromethoxylated indolines in 50–84% isolated yields up 37:1 diastereoselectivity, fluorinated trifluoromethoxylated were obtained exclusive trans selectivity. addition, conditions compatible other heteroaromatic rings as well styrene moieties.

Язык: Английский

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Total Synthesis of Alanense A through an Intramolecular Friedel–Crafts Alkylation

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(3), С. 2050 - 2054

Опубликована: Янв. 19, 2024

The first total synthesis of cadinane sesquiterpenoid alanense A, in which an intramolecular dehydrative Friedel–Crafts alkylation 2,5-diaryl-2-pentanol is incorporated as a key step, has been achieved. combinatorial use p-TsOH·H2O catalyst and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) solvent provides 1,1-disubstituted tetrahydronaphthalene 97% yield. It was also found that the combination p-TsOH HFIP effective for removal phenolic MOM ether.

Язык: Английский

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One-Pot Synthesis of N-Fused Quinolone-4 Tetracyclic Scaffolds from 2,2-Disubstituted Indolin-3-ones

ACS Omega, Год журнала: 2024, Номер 9(45), С. 45501 - 45517

Опубликована: Окт. 29, 2024

A cascade transformation of C2-quaternary indoxyls leading to an efficient assembly complex (dihydro)indolo[1,2-a]quinolin-5-one ring systems is reported. The method involves the gram-scale preparation 2-(2-aryl-3-oxoindolin-2-yl)-2-phenylacetonitriles which are then converted with methyl ketones corresponding 2-(2-oxo-2-aryl(alkyl)ethyl)-2-phenylindolin-3-ones. latter can either be isolated good yields (75–96%) or, in case o-nitroacetophenone, used situ for further base-assisted intramolecular SNAr cyclization resulting indoxyl-fused quinolone-4 hybrids (up 95%).

Язык: Английский

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Novel Two-Step Synthesis of N-Alkylated 2,3-Diaryl-4-quinolones

Synthesis, Год журнала: 2023, Номер 56(03), С. 435 - 444

Опубликована: Дек. 6, 2023

Abstract A library of 18 polysubstituted 4-quinolones was conveniently prepared via simple and practical protocol involving N-alkylation 2-(3-oxoindolin-2-yl)acetonitriles following NaH-induced ring expansion. The current two-step approach provides feasible access to a subclass N-protected C3-aryl-substituted 2-phenyl-4-quinolones starting with or just one step away from commercially available 2-arylindoles nitrostyrenes.

Язык: Английский

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Attempted Synthesis of the Central 2,2-Disubstituted Pseudoindoxyl Core of Austamide via a [Au]-Catalyzed Nitroalkyne Cycloisomerization and Intramolecular [3 + 2]-Cycloaddition

Tetrahedron, Год журнала: 2024, Номер 167, С. 134301 - 134301

Опубликована: Окт. 10, 2024

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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