Journal article
Synthesis of (Arylamido)pyrrolidinone Libraries through Ritter-Type Cascade Reactions of Dihydroxylactams : Synthesis of (Arylamido)pyrrolidinone Libraries
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.
Language: | English |
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Publisher: | WILEY‐VCH Verlag |
Year: | 2015 |
Pages: | 5633-5639 |
ISSN: | 10990690 and 1434193x |
Types: | Journal article |
DOI: | 10.1002/ejoc.201500712 |
ORCIDs: | Wu, Peng and Clausen, Mads Hartvig |