title: Benzotriazolyl-mediated 1,2-shifts of electron-rich heterocycles.
abstract: The anion formed from the lithiation of 1-[(methylthio)methyl]-1H-benzotriazole 1 with n-BuLi adds to heteroaryl ketones to give 2-benzotriazolyl alcohols 3a-m. Thermolysis of 3a-g in the presence of zinc bromide induces a 1,2-shift of heteroaromatic groups to form ketones 4a-g. By contrast, in the rearrangement of 2-benzotriazolyl alcohols 3h,i,k-m migration of the phenyl group rather than the corresponding heteroaromatic groups occurred to give ketones 4h,i,k-m.
authors.affiliation: Center for Heterocyclic Compounds, University of Florida, Department of Chemistry, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu
authors.forename: Alan R
authors.initials: AR
authors.lastname: Katritzky
authors.forename: Sergey
authors.initials: S
authors.lastname: Bobrov
authors.forename: Niveen
authors.initials: N
authors.lastname: Khashab
authors.forename: Kostyantyn
authors.initials: K
authors.lastname: Kirichenko