Abstract Benzyne and its 3, 4, 5, 6-tetraphenyl, 3-and 4-methyl, 3-methoxy and 4, 5-difluoro derivatives react with acetic acid 2-selenoxo-2H-pyridin-1-yl esters 4a-e to give benzo [b] seleno [2, 3-b] pyridines 10–15 in modest yields. The benzynes were generated by one or more of the following methods: diazotization of anthranilic acids 5a-g with isoamyl nitrate; mild thermal decomposition of 2-diazoniobenzenecarboxylate hydrochlorides 6a-d ...