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Gold(I)-Catalyzed Intramolecular Bicyclization: Divergent Construction of Quinazolinone and Ampakine Analogues.
Liu, Chao; Bolognani, Adriano; Song, Liangliang; Van Meervelt, Luc; Peshkov, Vsevolod A; Van der Eycken, Erik V.
Affiliation
  • Liu C; Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium.
  • Bolognani A; Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium.
  • Song L; 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 Material
  • Van Meervelt L; Biomolecular Architecture, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium.
  • Peshkov VA; College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou 215123, P. R. China.
  • Van der Eycken EV; Department of Chemistry, School of Sciences and Humanities, Nazarbayev University, 53 Kabanbay Batyr Ave, Nur-Sultan 010000, Republic of Kazakhstan.
Org Lett ; 24(46): 8536-8541, 2022 11 25.
Article in En | MEDLINE | ID: mdl-36374298
ABSTRACT
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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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Quinazolinones / Gold Type of study: Guideline Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2022 Document type: Article Affiliation country:
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Quinazolinones / Gold Type of study: Guideline Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2022 Document type: Article Affiliation country: