Gold(I)-Catalyzed Intramolecular Bicyclization: Divergent Construction of Quinazolinone and Ampakine Analogues
Liu C. Bolognani A. Song L. Van Meervelt L. Peshkov V.A. Van Der Eycken E.V.
25 November 2022American Chemical Society
Organic Letters
2022#24Issue 468536 - 8541 pp.
A gold(I)-catalyzed cascade intramolecular cyclization of Ugi adducts for the divergent construction of quinazolinone and ampakine analogues has been developed in a rapid, highly efficient and step-economical manner. This protocol shows high yields, excellent functional-group tolerance, broad substrate scope and excellent chemo- and regioselectivity. The practicality of this strategy is further demonstrated by a scale-up reaction. Diverse oligopeptides are also found to be well tolerated, affording polycyclic products decorated with a peptide chain.
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Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven, B-3001, Belgium
Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Jiangsu Key Lab of Biomass-Based Green Fuels and Chemicals, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, Jiangsu, Nanjing, 210037, China
Biomolecular Architecture, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven, 3001, Belgium
College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, China
Department of Chemistry, School of Sciences and Humanities, Nazarbayev University, 53 Kabanbay Batyr Ave, Nur-Sultan, 010000, Kazakhstan
Peoples Friendship University of Russia (RUDN University), Miklukho-Maklaya Street 6, Moscow, 117198, Russian Federation
Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC)
Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass
Biomolecular Architecture
College of Chemistry
Department of Chemistry
Peoples Friendship University of Russia (RUDN University)
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