Synthesis of benzoxazole crown ether cyanine dyes

Abstract

Beckmann rearrangement reaction of 2,3,4-trihydroxyacetophenone oxime gave 2-methyl-6,7-dihydroxybenzoxazole (I), which was treated with triglycol dichloride to give 2-methyl-6,7-benzo(12-crown-4)-benzoxazole (II). The II, quaternized with EtI, was reacted with Et orthoformate to give the corresponding benzoxazole crown ether cyanine dye or with p-dimethylaminobenzaldehyde to give hemicyanines. Benzoxazole 15-crown-5 cyanine and hemicyanine dyes were prepared similarly from I and tetraglycol dichloride.

Key words: ACETOPHENONE P, CROWN ETHER COMPOUNDS, PHOTOSENSITIVE DRUG, OXIME, CYANINE DYES, TRITHYLENE GLYCOL, QUATERNARY AMMONIUM COMPOUNDS

CLC Number:

O644

Cite this article

LIU XIUFANG;TU RONGHUA;XU HANSHENG. Synthesis of benzoxazole crown ether cyanine dyes[J]. Chin. J. Org. Chem., 1992, 12(4): 405-408.

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