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

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 655 - 655

Published: Jan. 1, 2025

Language: 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, Journal Year: 2024, Volume and Issue: 89(12), P. 8641 - 8655

Published: June 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

Language: Английский

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

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(14), P. 1904 - 1907

Published: Jan. 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.

Language: Английский

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Benzocyclobutenone Synthesis Exploiting Acylsilanes as Photofunctional Directing Groups

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

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

Language: Английский

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

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 211 - 257

Published: Jan. 1, 2024

Language: Английский

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