Benzotriazolyl-Mediated 1,2-Shifts of Electron-Rich Heterocycles

by Bobrov, S., Khashab, N., Kirichenko, K., Katritzky, A. R.
Year: 2004


Bobrov, S.; Khashab, N.; Kirichenko, K.; Katritzky, A. R. Benzotriazolyl-Mediated 1,2-Shifts of Electron-Rich Heterocycles. J. Org. Chem. 2004, 69, 4269-4271



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.


Benzotriazolyl 1 2-shifts Heterocycles