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

Z Guan, S Wiechmann, M Drafz, E Hübner…

Index: Guan, Zong; Wiechmann, Sascha; Drafz, Martin; Huebner, Eike; Schmidt, Andreas Organic and Biomolecular Chemistry, 2013 , vol. 11, # 21 p. 3558 - 3567

Full Text: HTML

Citation Number: 12

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.