Beilstein J. Org. Chem.2015,11, 385–391, doi:10.3762/bjoc.11.44
substitution. The use of diethyl 2-ethoxymethylidenemalonate in this reaction resulted in ethyl 7-hydroxytetrazolo[1,5-a]pyrimidine-6-carboxylate, while ethyl2-ethoxymethylidenecyanoacetate yielded 5-[2,6-diamino-3,5-bis(ethoxycarbonyl)pyridinium-1-yl]tetrazol-1-ide through an alternative pathway. Ethyl 2
; diethyl 2-ethoxymethylidenemalonate; 2-ethoxymethylidene-3-oxo esters; ethyl2-ethoxymethylidenecyanoacetate; Introduction
2-Ethoxymethylidene-1,3-dicarbonyl compounds are widely recognized as valuable building blocks in designing various open-chain and heterocyclic compounds, including those used in
esters 1a–d and their analogues (diethyl 2-ethoxymethylidenemalonate (1e), ethyl2-ethoxymethylidenecyanoacetate (1f)) with 5-AT as a synthetic approach to various azahetrocycles.
Results and Discussion
It has been found that 2-ethoxymethylidene-3-oxo esters 1a–c react with 5-AT in ethanol under reflux
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Graphical Abstract
Scheme 1:
Interaction of 2-ethoxymethylidene-3-oxo esters 1a–c with 5-AT. R = CF3 (a), (CF2)2H (b), Me (c). C...