title: 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.
authors.affiliation: Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, D-38678 Clausthal-Zellerfeld, Germany.
authors.forename: Zong
authors.initials: Z
authors.lastname: Guan
authors.forename: Sascha
authors.initials: S
authors.lastname: Wiechmann
authors.forename: Martin
authors.initials: M
authors.lastname: Drafz
authors.forename: Eike
authors.initials: E
authors.lastname: Hübner
authors.forename: Andreas
authors.initials: A
authors.lastname: Schmidt
mesh_terms: D000585:Aminacrine / Q000737:chemistry*; D003500:Cyclization; D007191:Indazoles / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry
chemical_list: D007191:Indazoles; C030011:carbene; D010165:Palladium; D000585:Aminacrine; D008697:Methane