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- Title
Synthesis of (Arylamido)pyrrolidinone Libraries through Ritter-Type Cascade Reactions of Dihydroxylactams.
- Authors
Wu, Peng; Petersen, Michael Åxman; Petersen, Rico; Rasmussen, Martin Ohsten; Bonnet, Karine; Nielsen, Thomas E.; Clausen, Mads H.
- Abstract
The Ritter-type reaction of arylnitriles and N-acyliminium ions generated in situ from dihydroxy-γ-lactams gave tetrahydropyrrolo[2,3- d]oxazol-5-ones in excellent yields. A subsequent acidic hydrolysis in EtOH/H2O/TFA (trifluoroacetic acid) yielded new (arylamido)pyrrolidinones with excellent cis diastereoselectivity. A combined one-step Ritter-hydrolysis procedure proved to be of equal efficiency. This versatile method, which was successfully used for the construction of a screening library containing 706 molecules within the European Lead Factory consortium, provides a simple way to access new compounds incorporating an arylamido and a pyrrolidinone moiety, both of which are widely found in marketed drugs and in biologically active molecules.
- Subjects
PYRROLIDINONES; LACTAM derivatives; ARYL group; NITRILES; HETEROCYCLIC compounds; HYDROLYSIS
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 25, p5633
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201500712