4-氰基-3,4-二甲基-3-甲氧羰甲基-γ-丁内酰胺的合成

Synthesis of 4-Cyano-3,4-dimethyl-3-methoxycarbonylmethyl- γ-butyrolactam

以2,3 丁二酮和丙二腈为原料,经缩合、水解、胺化、氰基取代、重氮甲烷酯化等反应制得合成托尼卟吩A的重要中间体氰基二甲基甲氧羰甲基丁内酰胺的二立体异构体混合物,反应的总收率约为10%。采用高效液相色谱(HPLC)对产物进行分离,得到反式和顺式异构体产物,其质量分数分别为64 4%和33 7%,通过UV-vis、1HNMR、13CNMR、IR、MS和元素分析对产物结构进行了确认。

The distereoisomeric mixture of cyanodimethylmethoxycarbonylmethylbutyrolactam,which is the important intermediate of tolyporphin A,was synthesized with total yield of about 10% from 2,3-butandione and malononitrile through condensation,hydrolysis,amination,cyano-substitution and esterification with diazomethane.By means of HPLC the product was separated into the trans- and cis-isomers with mass percents of 64.6% and 33.7% respectively.Their structures were characterized by elementary analysis,UV-vis,~1HNMR,^(13)CNMR,IR and MS spectra.