A Metal-Free Direct Decarboxylative Fluoroacylation of Indole Carboxylic Acids with Fluorinated Acids

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

Published: Sept. 25, 2024

A straightforward preparation of diversified fluorinated indol-3-yl ketones was developed by the direct decarboxylative fluoroacylation indole carboxylic acids. The reaction could be performed on a gram scale under net conditions. Neither metal catalyst nor an additive employed. This methodology featured simple conditions, high efficiency, exclusive selectivity, broad substrate scope, and easy operation, which allowed it to meet green chemistry requirement modern pharmaceutical industry. Control experiments confirmed that radical process might involved in tandem sequence.

Language: Английский

Synthesis of arene-functionalized fused heterocyclic scaffolds via a regioselective cascade 1,4-conjugate addition/5-exo-dig annulation strategy

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(46), P. 9159 - 9172

Published: Jan. 1, 2023

Facile access to furan fused heterocyclic scaffolds through a regioselective cascade reaction of propargylamines with 4-hydroxy-2H-pyran-2-ones and 4-hydroxy-6-methylpyridin-2(1H)-one has been achieved. This presumably involves the formation ortho-alkynyl quinone methide (o-AQM), 1,4-conjugate addition, followed by 5-exo-dig annulation, 1,3-H shift process. Moreover, provides new efficient method for synthesis highly sterically congested 3-phenolic furo[3,2-c]pyran-4-ones furo[3,2-c]pyridin-4(5H)-ones ring from readily available starting materials in good high yields (50-82%) broad functional group compatibility single step. Significantly, strategy described here is easily scalable several useful synthetic transformations prepared arene-functionalized 4H-furo[3,2-c]pyran-4-ones were also performed.

Language: Английский

Rhodaelectro-Catalyzed Synthesis of Pyrano[3,4-b]indol-1(9H)-ones via the Double Dehydrogenative Heck Reaction between Indole-2-carboxylic Acids and Alkenes

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

Published: Nov. 12, 2024

A rhodaelectro-catalyzed double dehydrogenative Heck reaction of indole-2-carboxylic acids with alkenes has been developed for the synthesis pyrano[3,4-

Language: Английский