Reaction of 2-(N-Alkyl-p-hydroxyanilino)-1,4-benzoquinones with Diazomethane. N-(Alkyl-p-hydroxyanilino)-4,7-indazol-quinones and their Isomer N-Methylderivatives. Studies on Quinones VII

Article abstract of DOI:10.1007/BF00899675

The reaction of N-alkyl-p-hydroxyanilinobenzoquinones 1 a-d, its acetylderivatives 1 a₁-c₁ and the methoxyderivative 1 a₂ with diazomethan yields in dependence on the reaction-conditions the indazolquinones 2 a-d, 2 a₁-c₁ or 2 a₂, the 1-methylindazolquinones 3 a-d and 3 a₁-c₁, and finally the methoxy-1-methylindazolquinones 5 a-d.The 2-methyl-isomers 6 a-d are formed only in small amounts.Methylation of 2a with dimethylsulfate gives 5a and 6a in the ratio of appr. 2 to 1.Acetylation of 2 a-d with acetanhydride leads to the N-O-acetylderivates, which are easily hydrolyzed to 2 a₁-d₁ during work up; 3 a-d yields 3 a₁-d₁.The structures are established by the described crossexperiments and by spectroscopy (UV/VIS, IR, NMR). - Keywords: Anilinobenzoquinones, reaction with diazomethane; Indazolquinones; Tautomerism