Condensation of 2-alkoxypropenals with N,N- and N,O-1,2-binucleophiles. A route to 2-(1'-alkoxyvinyl)imidazo-lidines and -oxazolidines
Condensation of 2-alkoxypropenals with N,N- and N,O-1,2-binucleophiles. A route to 2-(1'-alkoxyvinyl)imidazo-lidines and -oxazolidines
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DOI：
10.1007/s10593-009-0213-y
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发表时间：
2008-12-01
影响因子：
1.5
通讯作者：
Funtikova, E. A.
中科院分区：
文献类型：
--
作者：
Keiko, N. A.;Vchislo, N. V.;Funtikova, E. A.
2-乙氧基原酸与二氨基乙烯在不同溶剂(CHCl（3), MeCN， H(2)O， DMSO）下室温缩合得到平衡混合物（1:1-1.5）的互变异构体2-（1′-乙氧基乙烯）-1,3-咪唑烷和2-乙氧基原酸的2-氨基乙基亚胺以及1,2-二（2′-乙氧基丙烯-同一氨基）乙烯。后者是很容易制备定量产率使用两倍过量的醛。(1)利用核磁共振表征了加热对环链互变异构平衡动力学的影响。2-烷氧丙烯与N-甲基和N，N'-二苯基-1,2-二氨基乙烯以及N-苯基氨基乙醇反应得到相应的取代咪唑烷，收率为43-95%。
Condensation of 2-ethoxypropenal with diaminoethylene in different solvents (CHCl(3), MeCN, H(2)O, DMSO) at room temperature gives an equilibrium mixture (1:1-1.5) of tautomeric 2-(1'-ethoxyvinyl)-1,3-imidazolidine and 2-aminoethylimine of 2-ethoxypropenal as well as 1,2-bis(2'-ethoxypropenyl-ideneamino)ethylene. The latter is readily prepared in quantitative yield using a twofold excess of the aldehyde. (1)H NMR was used to demonstrate the effect of heating on the dynamics of the ring-chain tautomeric equilibrium. Reaction of the 2-alkoxypropenals with N-methyl- and N,N'-diphenyl-1,2-diaminoethylenes and with N-phenylaminoethanol gives only the corresponding substituted imidazolidines in 43-95% yield.