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Title

Synthesis and regioselective functionalization of piperazin-2-ones based on Phe-Gly pseudodipeptides

AuthorsValdivielso, Ángel M. CSIC; Ventosa-Andrés, Pilar CSIC; García-López, M. Teresa CSIC; Herranz, Rosario CSIC ORCID; Gutiérrez-Rodríguez, Marta CSIC ORCID
KeywordsSynthetic methods
Nitrogen heterocycles
Pseudodipeptides
Molecular diversity
Regioselectivity
Issue Date2013
PublisherJohn Wiley & Sons
CitationEuropean Journal of Organic Chemistry: 155- 161 (2013)
AbstractThe synthesis of 1,4-unsubstituted piperazin-2-ones by one-pot reductive cyclization of Pheο[CH(CN)NH]Gly pseudodipeptides is described. Studies on the reactivity of the piperazin-2-one ring showed a higher reactivity at the N4 position than at the N1 position. The stepwise regioselective functionalization of piperazin-2-one derivatives showed great potential for molecular diversity generation. An easy methodology for the synthesis of the piperazin-2-ones by one-pot reductive cyclization of Pheο[CH(CN)NH]Gly pseudodipeptides is described. Study of the reactivity of the piperazin-2-one ring has shown that regioselective functionalization at the N1 and N4 positions is possible, and hence great potential for molecular diversity generation.
URIhttp://hdl.handle.net/10261/101652
DOIhttp://dx.doi.org/10.1002/ejoc.201201221
Identifiersdoi: 10.1002/ejoc.201201221
issn: 1434-193X
e-issn: 1099-0690
Appears in Collections:(IQM) Artículos
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