Gold(I)-Catalyzed Intramolecular Bicyclization: Divergent Construction of Quinazolinone and Ampakine Analogues

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. © 2022 American Chemical Society.

Authors
Liu C. , Bolognani A. , Song L. , Van Meervelt L. , Peshkov V.A. , Van Der Eycken E.V.
Journal
Organic Letters
Number of issue
46
Language
English
Pages
8536-8541
Status
Published
Link
External link
DOI
10.1021/ACS.ORGLETT.2C03547
Volume
24
Year
2022
Organizations
  • 1 Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven, B-3001, Belgium
  • 2 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
  • 3 Biomolecular Architecture, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven, 3001, Belgium
  • 4 College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, China
  • 5 Department of Chemistry, School of Sciences and Humanities, Nazarbayev University, 53 Kabanbay Batyr Ave, Nur-Sultan, 010000, Kazakhstan
  • 6 Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya Street 6, Moscow, 117198, Russian Federation
Keywords
Catalysis; Cyclization; Gold; Quinazolinones; gold; quinazolinone derivative; catalysis; chemistry; cyclization
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