Journal of Heterocyclic Chemistry p. 129 - 139 (1995)
Update date:2022-08-17
Topics:
Shiotani
Tsuno
Tanaka
Tsuiki
Itoh
Ethyl 2-(3-furopyridyl)acetates 10a-d were synthesized from furopyridin-3(2H)-ones 4a-d by the Wittig-Horner reaction with diethyl cyanomethylphosphonate, hydrolysis and the subsequent esterification. Reaction of compounds 10a-d with lithium diisopropylamide (LDA) gave the corresponding methylene-lithiated intermediate, and the subsequent reaction with benzaldehyde, acetone and iodomethane afforded the methylene-alkylated product respectively, while N,N-dimethylacetamide did not give any reaction product. The 2-position of 10a, b and d is alkylated by the lithiation with excess of LDA and the successive reaction with an electrophile.
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