Directing Group-Controlled Regioselective [4 + 3] Annulation of Indole-2-Carboxamides with MBH Carbonates toward Highly Substituted Indole-1,2-Fused Diazepanones DOI
Shutao Wang, W. Y. Zhang,

Zhuoqi Zhang

и другие.

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

Опубликована: Апрель 11, 2025

A Lewis base-catalyzed [4 + 3] annulation between dinucleophilic indole-2-carboxamides and Morita-Baylis-Hillmann (MBH) carbonates was developed to access densely substituted indole-1,2-fused diazepanones. This reaction is initiated by a N-allylic alkylation of the indole scaffold with MBH carbonates, followed intramolecular Michael cyclization. Notably, selectivity this process controlled removable o-methoxyphenyl (OMP) directing group attached indole-2-carboxamides. The wide scope substrates, high regio- stereoselectivity, diverse transformations highlight potential synthetic utility method in drug discovery.

Язык: Английский

Directing Group-Controlled Regioselective [4 + 3] Annulation of Indole-2-Carboxamides with MBH Carbonates toward Highly Substituted Indole-1,2-Fused Diazepanones DOI
Shutao Wang, W. Y. Zhang,

Zhuoqi Zhang

и другие.

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

Опубликована: Апрель 11, 2025

A Lewis base-catalyzed [4 + 3] annulation between dinucleophilic indole-2-carboxamides and Morita-Baylis-Hillmann (MBH) carbonates was developed to access densely substituted indole-1,2-fused diazepanones. This reaction is initiated by a N-allylic alkylation of the indole scaffold with MBH carbonates, followed intramolecular Michael cyclization. Notably, selectivity this process controlled removable o-methoxyphenyl (OMP) directing group attached indole-2-carboxamides. The wide scope substrates, high regio- stereoselectivity, diverse transformations highlight potential synthetic utility method in drug discovery.

Язык: Английский

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