L. Xiu
1992
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Journal
Chinese Journal of Organic Chemistry
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.