Issue 21, 2013

Pericyclic rearrangements of N-heterocyclic carbenes of indazole to substituted 9-aminoacridines

Abstract

On deprotonation, 1-arylindazolium salts form 1-arylindazol-3-ylidenes which rearrange spontaneously via ring cleavage, ring closure and subsequent proton transfer to substituted 9-aminoacridines. By contrast, the N-heterocyclic carbene of 2-phenylindazolium cannot rearrange similarly and was trapped by sulfur.

Graphical abstract: Pericyclic rearrangements of N-heterocyclic carbenes of indazole to substituted 9-aminoacridines

Supplementary files

Article information

Article type
Paper
Submitted
21 Feb 2013
Accepted
08 Apr 2013
First published
08 Apr 2013

Org. Biomol. Chem., 2013,11, 3558-3567

Pericyclic rearrangements of N-heterocyclic carbenes of indazole to substituted 9-aminoacridines

Z. Guan, S. Wiechmann, M. Drafz, E. Hübner and A. Schmidt, Org. Biomol. Chem., 2013, 11, 3558 DOI: 10.1039/C3OB40379C

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