Base-Promoted One-Pot Strategy for Expeditious Assembly of Highly Functionalized Benzocoumarin Derivatives DOI

Fataneh Rakaee,

Morteza Shiri, Behnaz Farajpour

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 18, 2024

A versatile and atom-economic three-component reaction between 3-cyano-4-styrylcoumarins, 1,3-indandione, aliphatic alcohols is described for synthesizing diversely multifunctionalized benzocoumarins. This strategy allows facile access to various benzocoumarins bearing an amine a substituted benzoyl scaffold under simple heating conditions. Readily available precursors, operational simplicity, acceptable functional group tolerance, excellent yields are some highlighted advantages of this transformation.

Language: Английский

Synthesis of 6H-Benzo[c]chromene Scaffolds: A Synthetic Strategy of Pd-Catalyzed Annulation Followed by Aerial Oxidation DOI

Kangkana Chutia,

Pallabi Saikia, Dhiraj Dutta

et al.

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

Published: Jan. 3, 2025

A synthetic strategy of a palladium-catalyzed cascade annulation reaction followed by aerial oxidation was designed to construct 6H-benzo[c]chromene scaffolds. Various 6H-benzo[c]chromenes were synthesized under mild conditions using easily accessible p-QMs and commercially available o-hydroxyarylboronic acids. One the chromenes has been ambiguously confirmed single-crystal XRD analysis. Interestingly, our could be transformed into valuable 6H-benzo[c]chromen-6-ones via oxidation.

Language: Английский

Citations

3
Phosphine-Catalyzed Cascade Cycloaddition of Vinyl Oxiranes with Sulfonium Compounds to Step-Economically Construct Spiro-2(3H)-furanone Scaffolds DOI
Thomas P. Yang, Wei Du,

Chia‐Yu Wu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 9, 2025

In this work, we developed a phosphine-catalyzed cascade lactonization/[2 + 1] annulation reaction between vinyl oxiranes and sulfonium compounds for the highly diastereoselective construction of spiro-2(3H)-furanone skeletons. The cycloaddition proceeds via 2(5H)-furanone phosphonium intermediate, introducing an oxygen-containing active intermediate phosphine catalysis. These findings highlight significant potential harnessing as versatile synthons constructing spirocyclic through simultaneous multicyclic skeleton formation.

Language: Английский

Citations

0
DMAP Catalyzed Ring-Opening/Cycloaddition of Vinyl Oxiranes with Activated Ketone Compounds to Construct the 1,3-Dioxolane Skeletons DOI

Jiaxin Qu,

Thomas P. Yang, Xin Zhao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9322 - 9327

Published: Oct. 24, 2024

The present work develops a DMAP-catalyzed [3 + 2] cycloaddition of vinyl oxiranes with activated ketone compounds, affording dioxolane derivatives moderate to excellent yields. This approach represents the first Lewis base (LB)-catalyzed ring-opening reaction epoxides, simultaneously providing rare oxygen-containing active intermediate in this field. gram-scale preparation and facile derivatization cycloadduct highlight significant synthetic potential strategy.

Language: Английский

Citations

2
Base-Promoted One-Pot Strategy for Expeditious Assembly of Highly Functionalized Benzocoumarin Derivatives DOI

Fataneh Rakaee,

Morteza Shiri, Behnaz Farajpour

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 18, 2024

A versatile and atom-economic three-component reaction between 3-cyano-4-styrylcoumarins, 1,3-indandione, aliphatic alcohols is described for synthesizing diversely multifunctionalized benzocoumarins. This strategy allows facile access to various benzocoumarins bearing an amine a substituted benzoyl scaffold under simple heating conditions. Readily available precursors, operational simplicity, acceptable functional group tolerance, excellent yields are some highlighted advantages of this transformation.

Language: Английский

Citations

0