Transition metal-free selective C-S bond cleavage of Ugi-adducts for rapid preparation of peptidomimetics

A transition metal-free C-S bond cleavage and subsequent Mannich reaction of Ugi-adducts with alcohols as well as thiols is developed. Diverse novel peptidomimetics containing N,O- or N,S-aminals are synthesized in a rapid, highly efficient and step-economical fashion. This method features exclusive selectivity, broad substrate scope, excellent yield and functional group tolerance, and was applied on substrates derived from the pharmaceuticals febuxostat, probenecid and memantine. © 2022 The Royal Society of Chemistry.

Authors
Liu C.1 , Song L.2 , Peshkov V.A.3, 4 , Van Der Eycken E.V.
Journal
Green Chemistry
Publisher
Royal Society of Chemistry
Number of issue
7
Language
English
Pages
2783-2787
Status
Published
Link
External link
DOI
10.1039/d1gc04421d
Volume
24
Year
2022
Organizations
  • 1 Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), KU Leuven Celestijnenlaan 200F, Department of Chemistry, Leuven, 3001, Belgium
  • 2 Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, Nanjing Forestry University, College of Chemical Engineering, International Innovation Center for Forest Chemicals and Materials, Jiangsu Key Lab of Biomass-Based Green Fuels and Chemicals, Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Jiangsu, Nanjing, 210037, China
  • 3 College of Chemistry, Soochow University, Chemical Engineering and Materials Science, Dushu Lake Campus, Suzhou, 215123, China
  • 4 Department of Chemistry, Nazarbayev University, School of Sciences and Humanities, 53 Kabanbay Batyr Ave, Nur-Sultan, 010000, Kazakhstan
  • 5 Peoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya Street 6, Moscow, 117198, Russian Federation
Keywords
Chemical bonds; Chemical reactions; Substrates; C-S bond cleavage; Mannich reactions; Memantine; Metal free; Peptidomimetics; Probenecid; Synthesised; Transition metals
Date of creation
06.07.2022
Date of change
06.07.2022
Short link
https://repository.rudn.ru/en/records/article/record/83760/
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