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冠醚苯并恶唑菁染料的合成
引用本文:刘秀芳,涂荣华,徐汉生.冠醚苯并恶唑菁染料的合成[J].有机化学,1992,12(4):405-408.
作者姓名:刘秀芳  涂荣华  徐汉生
作者单位:武汉大学化学系,武汉大学化学系,武汉大学化学系 湖北,武汉,430072,湖北,武汉,430072,湖北,武汉,430072
摘    要:本文报道含冠迷苯并恶唑菁染料及半菁染料的合成,采用一种简便方法合成了关健中间体2-甲基6,7-二羟基苯并恶唑:从2,3,4-三羟基苯乙酮肟经beckmann重排而得到,将它再与三甘醇或四甘醇二氯化物反应 ,分别得到相应的冠醚化合物:2-甲基-6,7-并(12-冠-4)苯并恶唑和2-甲基-6,7-并(15-冠-5)苯并恶唑,将它们制成相应的季铵盐 ,然后分别与原甲酸乙酯或对二甲胺基甲醛作用,得到相应的冠醚恶唑菁染料,或半菁染料.

关 键 词:冠式化合物  苯乙酮  P    三甘醇  菁染料  光敏剂  季胺  苯并恶唑  P  半菁染料  多甘醇

Synthesis of benzoxazole crown ether cyanine dyes
LIU Xiu-Fang,TU Rong-Hua,XU Han-Sheng.Synthesis of benzoxazole crown ether cyanine dyes[J].Chinese Journal of Organic Chemistry,1992,12(4):405-408.
Authors:LIU Xiu-Fang  TU Rong-Hua  XU Han-Sheng
Institution:LIU Xiu-Fang,TU Rong-Hua,XU Han-Sheng Department of Chemistry,Wuhan University,430072 Wuhan,Hubei
Abstract:2-methyl-6, 7-dihydroxyl benzoxazole was synthesized from 2,3, 4-trihydroxyl ace-tophenone oxime via Beckmann rearrangement conveniently. Then treatment of the dihydro-xyl benzoxazole with triglycol dichloride gave 2-methyl-6, 7-(12-crown-4) benzoxazole (1).Quaternization of 1 by ethyl iodide yielded 3. The reaction of quaternary ammonium salt 3with ethyl orthoformate then afforded the coresponding benzoxazole crown ether cyanine dye5. The reaction of 3 with p-dimethylamino benzaldehyde gave the hemicyanines 7. Via thesimilar sequence. the benzoxazole (15-crown-5) cyanine dye (6) and hemicyanine 8 weresynthesized from 2-methyl-6, 7-dihydroxyl benzoxazole and tetraglycol dichloride.
Keywords:crown ether  cyanine dye  hemicyanine dye  benzoxazole  photosensitizer
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