Lateral deprotonation of N-Boc-1-amino-7-methylbenzotriazole 7 using BuLi–TMEDA leads to the synthetically useful dianion 18, which can be alkylated and which condenses smoothly with a range of aldehydes, ketones and epoxides to provide derivatives (19, 20 and 21 respectively), which are potentially useful in the generation of substituted benzynes.
M. A. Birkett, D. W. Knight, R. G. Giles and M. B. Mitchell, J. Chem. Soc., Perkin Trans. 1, 1998, 2301 DOI: 10.1039/A803251C
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