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Issue 16, 2017, Issue in Progress
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Oxidation of diazenyl-protected N-heterocycles – a new entry to functionalized lactams

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Abstract

Functionalized 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.

Graphical abstract: Oxidation of diazenyl-protected N-heterocycles – a new entry to functionalized lactams

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Publication details

The article was received on 09 Nov 2016, accepted on 15 Dec 2016 and first published on 31 Jan 2017


Article type: Paper
DOI: 10.1039/C6RA26546D
Citation: RSC Adv., 2017,7, 9461-9464
  • Open access: Creative Commons BY license
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    Oxidation of diazenyl-protected N-heterocycles – a new entry to functionalized lactams

    M. Petrović, D. Scarpi, M. Nieger, N. Jung, E. G. Occhiato and S. Bräse, RSC Adv., 2017, 7, 9461
    DOI: 10.1039/C6RA26546D

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