ACS Sustainable Chemistry and Engineering.
American Chemical Society.
Vol. 10.
2022.
P. 3335-3345
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
Publisher
Royal Society of Chemistry
Number of issue
7
Language
English
Pages
2783-2787
Status
Published
Link
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
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