Anil Synthesis in the Design of Push−Pull Systems. Synthesis of 2- and 4-(4-Styrylphenyl)-substituted Diphenylpyrimidines
Russian Journal of Organic Chemistry(2020)
摘要
The potential of anil synthesis for the preparation of 2,4,6-triaryl-substituted pyrimidines with an extended chain of delocalized π-bonds was studied. The reaction of ( E )-3-phenyl-1-( p -tolyl)prop-2-en-1-one or chalcone with benzamidine, 4-methylbenzamidine, or 4-isobutoxybenzamidine hydrochlorides in ethanol in the presence of KOH gave 2,4-diphenyl-6-( p -tolyl)pyrimidine, 4,6-diphenyl-2-( p -tolyl)pyrimidine, and 2-(4-isobutoxyphenyl)-4-phenyl-6-( p -tolyl)pyrimidine. The synthesized pyrimidines were reacted with ( E )- N -(phenyl- or 2-chlorophenyl)-1-arylmethanimines in DMF in the presence of a KOH/LiH mixture to obtain ( E )-4,6-diphenyl-2-(4-styrylphenyl)pyrimidines and ( E )-2,6-diphenyl-4-(4-styrylphenyl)pyrimidines were obtained.
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关键词
2,4-diphenyl-6-(p-tolyl)pyrimidine,4,6-diphenyl-2-(p-tolyl)pyrimidine,2-(4-isobutoxyphenyl)-4-phenyl-6-(p-tolyl)pyrimidine,(E)-3-phenyl-1-(p-tolyl)prop-2-en-1-one,chalcone,condensation,DMF/KOH/LiH,(E)-4,6-diphenyl-2-(4-styrylphenyl)pyrimidines,(E)-2,6-diphenyl-4-(4-styrylphenyl)pyrimidines
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