DBU骨架含N杂环的合成及产物的核磁共振分析

摘要

DBU (1,8-diazabicyclo [5.4.0]undec-7-ene)-skeleton N-containing heterocycles were synthesized through the cyclization reaction between N-benzyl-N-phenyl-3-arylpropiolamide with DBU in acetonitrile at 80 ℃. Weinreb amide also could react with DBU and give the same skeleton products.When ethyl 3-phenylpropiolate reacted with DBU at 80 ℃ in acetonitrile,two DBU-skeleton N-containing heterocycle isomers were obtained.Its structure was elucidated by 1D (1 H-NM R,13 C-NM R) and 2D (1 H-detected heteronuclear multiple bond correlation) nuclear magnetic spectra and mass spectra.%1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)与N-苯基-N-苄基苯丙炔酰胺化合物在80℃下以乙腈为溶剂反应,得到DBU骨架的三元并环含氮杂环化合物.进一步以苯丙炔weinreb酰胺为底物研究了该反应,含有苯基、对甲苯基、对氯苯基和间氯苯基的苯丙炔weinreb酰胺均能与DBU反应得到相应的并环含氮杂环化合物.当苯丙炔酸乙酯与DBU在80℃下以乙腈为溶剂反应时,得到了以DBU为骨架的两种同分异构体,通过一维(1H-NMR,13C-NMR)与碳氢远程相关二维(HMBC)核磁共振谱图、质谱等对产物的结构进行了确认.