B. F. Kukharev, N. Lobanova, V. Stankevich
May 5, 2012
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Journal
Russian Journal of Organic Chemistry
Abstract
Vinyl ethers derived from amino alcohols are promising mitrogen-containing monomers and starting compounds for the synthesis of biologically active substances [1]. They can be synthesized by reactions of vinyl ethers containing an epoxy group, in particular glycidyl vinyloxyalkyl ethers, with various primary and secondary aliphatic, aromatic, and heterocyclic amines [2]. Reactions of 2-(vinyloxymethyl)oxiranes (glycidyl vinyl ethers) with amines having hydroxyalkyl groups on the nitrogen remain almost unknown. An exception is their reaction with 2-aminoethanol and 2,2′-iminodiethanol, leading exclusively to the formation of N-hydroxyalkyl derivatives [3]. Numerous examples demonstrated [4] that alcohols react with 2-(vinyloxymethyl)oxiranes as with typical aliphatic epoxy compounds to give the corresponding alcohol hydroxyalkylation products [4]. In the present work we examined reactions of ethylene glycol ether I with N,N-disubstituted amino alcohols IIa and IIb. Oxirane derivative I was heated with 3 equiv of 2-(dimethylamino)or 2-(diethylamino)ethanol IIa or IIb at 75–85°C over a period of 2 h. Excess amino alcohol II was necessary to suppress polymerization at the epoxy group. At an equimolar ratio of compounds I and IIa or IIb the yield of polymeric products was 45 and 31%, respectively. Hydroxyalkylation of 2-(dialkylamino)ethanols IIa and IIb involved both hydroxy and amino groups. Oxiranes are known to react with tertiary amines to form quaternary ammonium bases (see, e.g., [5]) and