Smart Hybrid Materials (SHMs)
Khashab Research Group
Innovatively Functionalized Nanomaterials for Biomedical, Sensing and Composites Applications

Publication-1

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

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
‚Äč
Bobrov, S.; Khashab, N.; Kirichenko, K.; Katritzky, A. R.
Benzotriazolyl, 1, 2-shifts, heterocycles
2004



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-mThermolysis 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.