Ruthenium(ii)-catalyzed C–H activation/lactonization of aromatic acids with diazonaphthoquinones: regioselective synthesis of polycyclic coumarin frameworks

Literature Information

Publication Date 2023-10-09
DOI 10.1039/D3QO01450A
Impact Factor 5.281
Authors

Chandan Kumar Giri, Sudeshna Mondal, Mahiuddin Baidya


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Abstract

A straightforward synthesis of biologically relevant dibenzo[c,h]chromen-6-one and dibenzo[c,f]chromen-5-one frameworks has been accomplished by leveraging a one-pot annulative coupling of aromatic acids with diazonaphthoquinones under ruthenium catalysis. The protocol harnessed the assistance of weak coordination and displayed high reaction yields with broad functional group tolerance, scalability, and scaffold diversity. This annulation was also fruitful in the presence of diverse pharmacophore scaffolds including commercial drugs. The reaction involved a reversible C–H metalation step and a ruthenium(IV)-containing intermediate.

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Organic Chemistry Frontiers

Organic Chemistry Frontiers
CiteScore: 7.8
Self-citation Rate: 8.7%
Articles per Year: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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