Directed deprotonation of 7-methyl-1-aminobenzotriazole: an approach to ortho-substituted benzyne precursors

Abstract

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.

References

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