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

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 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.

Language: Английский

Synthesis of polysubstituted spiroazepines via [4 + 3] annulation reaction of ninhydrin-derived Morita−Baylis−Hillman carbonates with 1‑heterodienes DOI
Kai‐Kai Wang, Yafei Li, R. Bi

et al.

Journal of Molecular Structure, Journal Year: 2025, Volume and Issue: unknown, P. 141478 - 141478

Published: Jan. 1, 2025

Language: Английский

Citations

0
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

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 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.

Language: Английский

Citations

0