Reactions of 4-aryl-1-hydrazinophthalazines with carbonyl compounds.
Reaction of 1-hydrazino-4-phenylphthalazine and 4-benzyl-1-hydrazinophthalazine with different carbonyl compounds are described. With oxalic acid, the two cyclic amidrazones reacted to give 6-aryl-1,2,4-triazolo[3,4-a]phthalazines. Reaction with diethyl oxalate, however, afforded the corresponding 7-aryl-3,4-dioxo-1,2,4-triazino[3,4-a]phthalazines. With pyruvic acid, ethyl pyruvate, or methyl phenyl glyoxylate the corresponding hydrazones were obtained which were cyclized to 7-aryl-3-methyl or 7-aryl-3-phenyl-1,2,4-triazino[3,4-a]phthalazines, respectively. Whereas the reaction of the two cyclic amidrazones with acetylacetone or ethyl phenyl propiolate gave pyrazole derivatives, their reaction with ethyl acetoacetate gave 6-aryl-3-methyl-1,2,4-triazolo[3,4-a]phthalazines. The results of biological testing of representative examples of the prepared compounds as insecticides and nematicides are reported.
Shaban
M A
MA
Department of Chemistry, Faculty of Science, Alexandria University, Egypt.
Taha
M A
MA
Nasr
A Z
AZ
D000090:Acetoacetates / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D000818:Animals; D000969:Antinematodal Agents / Q000138:chemical synthesis*; D006834:Hydrazines / Q000138:chemical synthesis* / Q000494:pharmacology; D007313:Insecta; D007306:Insecticides / Q000138:chemical synthesis*; D007651:Keto Acids / Q000737:chemistry; D009348:Nematoda; D010070:Oxalates / Q000737:chemistry; D010422:Pentanones / Q000737:chemistry; D010793:Phthalazines / Q000138:chemical synthesis* / Q000494:pharmacology; D010944:Plants
D000090:Acetoacetates; D000480:Alkynes; D000969:Antinematodal Agents; D006834:Hydrazines; D007306:Insecticides; D007651:Keto Acids; D010070:Oxalates; D010422:Pentanones; D010793:Phthalazines; C015202:ethylphenylpropiolate; C008790:acetylacetone; C024840:ethyl acetoacetate