N-(2-苦胺基乙基)单氮杂冠醚的合成

研究并比较了氮支套索型生色冠醚1a和1b两条不同的合成路线, 结果表明, 由N-苦基乙二胺(2)与1,11-二碘-3,6,9-三氧杂十一烷进行N-烷基化环化反应, 可方便地制备N-(2-苦胺基乙基)单氮杂-12-冠-4(1a), 但按此法未能获得更大环的-15-冠-5(1b);若从N-对甲苯磺酰基乙二胺(6)或N-(2-对甲苯磺酰胺基乙基)二乙醇胺(7)出发, 经环化, 脱除对甲苯磺酰基而制得的N-(2-氨基乙基)单氮杂冠醚5a和5b分别与苦基氯反应, 则可获得高产率的生色生色冠醚11a和1b.

Synthesis of N-(2-picrylaminoethyl) monoazacrown ethers

Two different synthetic pathways for the chromogenic N-pivot lariat crown ethers (1a and 1b) were studied comparatively. It was found that N-(2-picrylaminoethyl) monoaza -12-crown-4 (1a) could be synthesized conveniently by the N-cycloalkylation of N-picrylethylenediamine (2) with 1,11-diiodo-3,6,9-trioxaundecane (3) but this method became invalid to obtain 15-crown-5 (1b), however the picryl chloride reacted with N-(2 -aminoethyl) monoazacrown ethers (5a and 5b), which were obtained via the cyclozation of N-tosylethylenediamine (6) or N-(2-tosylamidoethyl) diethanolamine (7) followed by detosylation giving 1a and 1b in good yield.