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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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Supplementary files

Article information


Submitted
09 Nov 2016
Accepted
15 Dec 2016
First published
31 Jan 2017

This article is Open Access

RSC Adv., 2017,7, 9461-9464
Article type
Paper

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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