A. I. Moskalenko, V. Boev
Nov 7, 2012
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Journal
Russian Journal of Organic Chemistry
Abstract
We recently developed a general procedure for the synthesis of spirocyclic 3-oxotetrahydrofurans having carboand heterocyclic fragments [1], which may be used in turn for the preparation of other potential biologically active heterocyclic compounds [2]. We now report on the reaction of one of such compounds, tert-butyl 3-oxo-1-oxa-8-azaspiro[4.5]decane-8-carboxylate (I), with N,N-dimethylformamide dimethyl acetal (II) which is known [3] to readily react with substrates containing an active methylene group. Compound I reacted with amino acetal II at a molar ratio of 1 : 1.5 in toluene (reaction 2 h) to give a mixture of isomeric condensation products IIIa and IVa (Scheme 1). Compounds IIIa and IVa were separated due to their different solubilities in hexane and were isolated in 44 and 17% yield, respectively.