Eingegangen a m 3 I . Januar 1969 p-Hydroxy-benzoldiazoniumchlorid (1) und 2.6-Dichlor-benzochinon-(1.4)-diazid-(4) (2) werden mit 3-b;thoxycarbonyl-piperidon-(2) (3) und rnit 2-Acetyl-4-cyan-buttersaureathylester (10) nach Japp und Klingemann zu den 4-Hydroxy-phenylhydrazonen 6 und 7 bzw. 11 und 12 umgesetzt. Die Hydrazone 6 und 7 lassen sich nach E. Fischer in die 5-Hydroxyindol-Derivate 8 und 9 iiberfiihren, wahrend das Hydrazon 12 zu den Tetrahydropyridazin-Derivaten 13 und 14 cyclisiert.
Reactions wirh Diazocarbonyl Compounds, XXXII1). Synthesis of' 2-Carboxy-5-hydroxytryptamine and Pyridazine Derivatives. Japp-Klingemann-Synthesis wirh p -Hydroxy-phenyl-diazonium Salts or p-Chinon-diazides, respectivelyp-Hydroxybenzenediazoniumchloride (1) and 2,6-dichloro-1,4-benzoquinone-4-diazide (2) react with 3-ethoxycarbonyl-2-piperidone (3) and with ethyl 2-acetyl-4-cyanobutyrate (10) (Japp-Klingemann synthesis) t o give 4-hydroxyphenylhydrazones 6, 7 and 11, 12, respectively. The hydrazones 6 and 7 are converted into the 5-hydroxyindole derivatives 8 and 9 (E. Fischer indole synthesis), while the hydrazone 12 is cyclized t o the tetrahydropyridazine derivatives 13 and 14.
Bei der Photolyse oder Thermolyse von Anthradichinon-(2.3 ; 9. IO)-diazid-(3) (1 a) in aromatischen Kohlenwasserstoffen erhalt man unter Nz-Abspaltung 2-Hydroxy-3-arylanthrachinone-(9.10) (Za, c, e, f ; Tab. 1).
Yates
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