Synthesis of (Arylamido)pyrrolidinone Libraries through Ritter-Type Cascade Reactions of Dihydroxylactams

Autor:	Martin Ohsten Rasmussen, Mads Hartvig Clausen, Karine Bonnet, Peng Wu, Thomas E. Nielsen, Michael Åxman Petersen, Rico Petersen
Rok vydání:	2015
Předmět:	Hydrolysis chemistry.chemical_compound chemistry Organic Chemistry Trifluoroacetic acid Molecule Moiety Organic chemistry Pyrrolidinones Physical and Theoretical Chemistry Combinatorial chemistry Ritter reaction
Zdroj:	European Journal of Organic Chemistry. 2015:5633-5639
ISSN:	1434-193X
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::a59988ddc47dad70dd808be4e672e021 https://doi.org/10.1002/ejoc.201500712 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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