ArticleChemMedChem2021
Coupling Interrupted Fischer and Multicomponent Joullié-Ugi to Chase Chemical Diversity: from Batch to Sustainable Flow Synthesis of Peptidomimetics.
Article in ChemMedChem, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Sustainable Joullié-Ugi and Continuous Flow Implementation Led to Novel Captopril-Inspired Broad-Spectrum Metallo-β-Lactamase Inhibitors.Journal of medicinal chemistry · 2025Article
- Diastereoselective ZnClMolecules (Basel, Switzerland) · 2024Article
- Rejuvenating the [1, 2, 3]-triazolo [1,5-a]quinoxalin-4(5Frontiers in chemistry · 2023Article
- Amide Bonds Meet Flow Chemistry: A Journey into Methodologies and Sustainable Evolution.ChemSusChem · 2022Review
- Coupling Interrupted Fischer and Multicomponent Joullié-Ugi to Chase Chemical Diversity: from Batch to Sustainable Flow Synthesis of Peptidomimetics.ChemMedChem · 2021Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
The generation of peptidomimetic substructures for medicinal chemistry purposes requires effective and divergent synthetic methods. We present in this work an efficient flow process that allows quick modulation of reagents for Joullié-Ugi multicomponent reaction, using spiroindolenines as core motifs. This sterically hindered imine equivalent could successfully be diversified using various isocyanides and amino acids in generally good space-time yields. A telescoped flow process combining interrupted Fischer reaction for spiroindolenine synthesis and subsequent Joullié-Ugi-type modification resulted in product formation in very good overall yield in less than 2 hours compared to 48 hours required in batch mode. The developed protocol can be seen as a general tool for rapid and facile generation of peptidomimetic compounds. We also showcase preliminary biological assessments for the prepared compounds.
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Registered trials
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