Synthesis of Substituted 1,2-Dihydroisoquinolines by Palladium-Catalyzed Cascade Cyclization–Coupling of Trisubstituted Allenamides With Arylboronic Acids

Published: June 7, 2024

1,2-Dihydroisoquinolines are important compounds due to their biological and medicinal activities, numerous approaches synthesis have been reported. In this study, a palladium-catalyzed cascade cyclization-coupling of trisubstituted allenamides containing bromoaryl moiety with arylboronic acids is described. The reaction proceeds via intramolecular cyclization, followed by transmetallation the acid resulting allylpalladium intermediate. A variety substituted 1,2-dihydroisoquinolines were concisely obtained using methodology because allenamides, as substrates, prepared from readily available propargylamines in one step.

Language: Английский

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Rhenium-catalyzed synthetic method of indanes and indenes through the C–C bond cleavage of 1,3-dicarbonyl compounds

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 147, P. 155212 - 155212

Published: July 23, 2024

Language: Английский

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Synthesis of Substituted 1,2-Dihydroisoquinolines by Palladium-Catalyzed Cascade Cyclization–Coupling of Trisubstituted Allenamides with Arylboronic Acids

Molecules, Journal Year: 2024, Volume and Issue: 29(12), P. 2917 - 2917

Published: June 19, 2024

1,2-Dihydroisoquinolines are important compounds due to their biological and medicinal activities, numerous approaches synthesis have been reported. Recently, we reported a facile of trisubstituted allenamides via N-acetylation followed by DBU-promoted isomerization, where various substituted were conveniently synthesized from readily available propargylamines with high efficiency. In light this research background, focused on the utility methodology for 1,2-dihydroisoquinolines. study, palladium-catalyzed cascade cyclization–coupling containing bromoaryl moiety arylboronic acids is described. When N-acetyl diphenyl-substituted allenamide phenylboronic acid treated 10 mol% Pd(OAc)2, 20 P(o-tolyl)3, 5 equivalents NaOH in dioxane/H2O (4/1) at 80 °C, reaction proceeded afford 1,2-dihydroisoquinoline. The intramolecular cyclization, transmetallation resulting allylpalladium intermediate. A variety highly 1,2-dihydroisoquinolines concisely obtained using because allenamides, as substrates, prepared one step.

Language: Английский

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Rhenium-catalyzed reaction of α-alkyl substituted β-dicarbonyl compounds with organosilicon compounds

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 154, P. 155390 - 155390

Published: Nov. 29, 2024

Language: Английский

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