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Oxidation of diazenyl-protected N-heterocycles-a new entry to functionalized lactams

Petrović, Martina; Scarpi, Dina; Nieger, Martin; Jung, Nicole; Occhiato, Ernesto G.; Bräse, Stefan

Abstract:
unctionalized lactams are an important class of heterocycles since they are useful intermediates in organic synthesis and show biological activity in diverse therapeutic applications. In the herein presented study, a strategy for the synthesis of N-aryldiazenyllactams, offering the direct access to protected lactam derivatives is described. After the formation of triazenes from diazonium salts and commercially available N-heterocycles, oxidation (directed CH activation) with periodate under ruthenium catalysis furnished N-diazenyllactams in one step. To demonstrate the suitability of the resulting lactams for further functionalizations, the alkylation of a N-diazenyllactam is presented for one example.


Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Institut für Toxikologie und Genetik (ITG)
Publikationstyp Zeitschriftenaufsatz
Jahr 2017
Sprache Englisch
Identifikator DOI: 10.1039/c6ra26546d
ISSN: 2046-2069
KITopen ID: 1000068584
HGF-Programm 47.01.01; LK 01
Erschienen in RSC Advances
Band 7
Heft 16
Seiten 9461-9464
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