142502-91-8Relevant articles and documents
Furopyridines. XII. Reaction of 3-Bromo, 2-Phenylthio and 2-Phenylthio-3-bromo Derivatives of Furo-, Furo-, Furo- and Furopyridine with Several Alkyllithiums
Shiotani, Shunsaku,Morita, Hiroyuki
, p. 413 - 422 (2007/10/02)
This paper describes reactions of 3-bromo- 1a-d, 2-phenylthio- 5a-d and 2-phenylthio-3-bromofuropyridines 6a-d with n-butyl-, t-butyl- and methyllithium and lithioacetonitrile.Lithiation of compounds 1a-d with n-butyl- or methyllithium gave the parent furopyridines 2a-d and o-ethynylpyridinols 3a-d.Reaction of compounds 5a-d with methyllithium afforded o-(phenylthioethynyl)pyridinols 7a-d, which were also yielded by reaction of compounds 6a-d with t-butyl- or methyllithium.The phenylthio group in compounds 7a-d were substituted with t-butyl group by the reaction with excess t-butyllithium.In contrast, 2-phenylthio group in compounds 5a-d and 6a-d was substituted with cyanomethyl group by reaction with lithioacetonitrile to give compounds 11a-d and 10b,c respectively.
