A route to ortho-substituted benzyne precursors by deprotonation of 7-methyl-1-aminobenzotriazole derivatives

Article abstract of DOI:10.1016/S0040-4039(00)91835-5

Double deprotonation of N-Boc-7-methyl-1-aminobenzotriazole 6 using (n)BuLi-TMEDA-THF [-78°C -> 0°C) results in an essentially quantitative conversion to the dianionic intermediate 7. Trapping at the carbon-centred anion occurs selectively under suitable conditions with alkylating agents, aldehydes and ketones to give good the excellent yields of the 7-substituted-1-aminobenzotriazoles 8-15, precursors of ortho-substituted benzynes.