lie'sume'. Les oximes des dihydro-9,10-4H-benzo [4,5] cyclohepta [l, 2-b] thiophhones-4 et leurs derives ont i t 6 synthktisds e t transposks selon Beckmann en benzo [b] In der vorliegenden Arbeit beschreiben wir die Synthese der Oxime und basisch substituierten Oximderivate I sowie verschiedene Umlagerungsreaktionen, die zu Azocinen fiihren. Bestandiger sind die Oximather (Tab. 1). Wir erhielten sie entweder aus den Oximen I (R' = H) mit Dialkylaminoalkylhalogeniden in athanolischer Natriumathylatlosung oder aus den Ketonen IV durch Kondensation mit w-Dialkylaniinoalkyloxyamin oder, neben Udagerungsprodukten, durch vorsichtiges Behandeln des Tosylats V rnit dem entsprechenden Aminoalkyl-alkohol.
918HELVETICA CHlMICA ACTA 9-(~-Didthylarni~zo-athyl)-l-hydroxy-l, 3-dimethyl-l12, 3,4-tetvahydvo-y-carbolan (X V I I ) : Behandelt man 8,16 g der oben beschriebenen sekundaren Base in 13 ml Eisessig mit 2,7 ml 40-proz. A new synthesis of y-carbolines is described. Starting from 2-lithium l-alkylindoles, reaction with an a-dialkylaminoketone yields 2-indolylethanolamines, which are aminomcthylated with formaldehyde and dimethylamine in the 3-position of the indole nucleus. The dimethylaminomethyl nitrogen of this gramine derivative may be selectively quaternized with methyl iodide and the quaternary gramine derivative cyclized to N(b)-quaternized 1-hydroxy-1 ,2,3,4-tetrahydro-y-carboline derivatives by hcating. Thc latter products may be aromatized at higher temperatures to quaternary y-carboline derivativcs. The generality of thc new method is verified by numerous examples.Forschungslaboratorien der CIBA AKTIENGESELLSCHAFT, Basel Pharmazeutische Abteilung
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