New method for the annelation of a pyridine ring on derivatives of imidazole and benzimidazole |
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Authors: | L M Potikha A R Turelyk V A Kovtunenko A V Turov |
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Institution: | (1) Taras Shevchenko Kiev National University, Kiev, 01033, Ukraine |
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Abstract: | The interaction of (Z)-1,3-diaryl-4-bromo-2-buten-1-ones with 1-substituted (benz)imidazoles in benzene gave (Z)-1-R-3-(2,4-diaryl-4-oxo-2-butenyl)-1H-imidazolium
bromides and (Z)-1-R-3-(2,4-diaryl-4-oxo-2-butenyl)-1H-benzimidazolium bromides which readily cyclize in the presence of base
to form derivatives of 7,9-diarylpyrido1,2-a]benzimidazole and 6,8-diarylpyrimidazo1,2-a]pyridine. The effects of the nature of substituents in the benzene ring of the diarylbutenones and the substituent at N(1)
in the (benz)imidazoles on the alkylation and cyclization reactions has been studied. The optimum conditions for the synthesis
of the 5-R-4-hydroxy-2,4-diphenyl-4,5-dihydro-1H-pyrido1,2-a]benz-imidazol-10-ium, 5-R-2,4-diaryl-4-hydroxy-4,5-dihydro-3H-pyrido1,2-a]benzimidazol-10-ium, and 5-R-2,4-diaryl-5H-pyrido1,2-a]benzimidazol-10-ium
have been found. |
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