Progress on Cobalt-Catalyzed C(sp²)—H Activation for the Construction of Nitrogen-Containing Benzo Heterocycles

Chinese Journal of Organic Chemistry, Год журнала: 2025, Номер 45(2), С. 655 - 655

Опубликована: Янв. 1, 2025

Язык: Английский

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Cyclocondensation of 2-(α-Diazoacyl)-2H-azirines with Amidines in Diazo Synthesis of Functionalized Naphtho[1,2-d]imidazoles

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 8641 - 8655

Опубликована: Июнь 7, 2024

A diazo approach toward functionalized naphtho[1,2-d]imidazole derivatives has been developed. It involved a new reaction of arylamidines with 2-(α-diazoacyl)-2H-azirines giving 5-aryl-4-(α-diazoacyl)-1H-imidazoles under mild conditions in good yields. The mechanism annulation azirines amidines is discussed based on DFT calculations. proceeds an unusual manner by cleavage the azirine C–C bond, allowing for transfer aryl substituent from arylamidine to proper position key intermediate synthesis. Under thermolysis conditions, undergo Wolff rearrangement followed selective 6π-cyclization transient ketene form 3H-naphtho[1,2-d]imidazoles bearing various substituents positions 2,3,4,5,7,8,9. Additionally, variation at 5 naphtho[1,2-d]imidazoles possible through formation triflates and subsequent cross-coupling reactions. One more heterocyclic pharmacophoric skeleton, 3H-furo[3′,2':3,4]naphtho[1,2-d]imidazole, was easily constructed methyl 5-hydroxy-3H-naphtho[1,2-d]imidazole-4-carboxylates one-pot mode using O-alkylation phenacyl bromides base-induced intramolecular acyl substitution room temperature high

Язык: Английский

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Benzocyclobutenone Synthesis Exploiting Acylsilanes as Photofunctional Directing Groups

Chemical Science, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

The visible-light irradiation of acylsilane tethered vinyl ketones promotes an intramolecular Stetter-type reaction

Язык: Английский

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DMF as amine source: iron-catalyzed cyclization of 2H-azirines to imidazoles

Chemical Communications, Год журнала: 2024, Номер 60(14), С. 1904 - 1907

Опубликована: Янв. 1, 2024

The Fe( ii )-catalyzed cyclization of 2 H -azirines and N , -dimethylformamide as an amine source has been developed for the synthesis 1-methyl-4,5-diaryl-1 -imidazoles.

Язык: Английский

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Five-membered ring systems: With more than 1 N atom

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 211 - 257

Опубликована: Янв. 1, 2024

Язык: Английский

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