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
Sunzmavy. Treatment of the arylhydrazones of 1,3-disubstitutcd 4-piperidones with ethanolic hydrogen chloride (FISCHER reaction conditions) affords 1,2,3,4-tetrahydropyrimido [3,4-a]-indoles in good yields. During catalytic hydrogenation in the presence of protons these tetrahydropyrimido-indoles are split into 2-(2-mcthylamino-ethyl)-indoles. The formation of these tricyclic products can be explained by rearrangement immediately following the normal FISCI~ER reaction.If the substituent at the piperidine nitrogen is an acyl group, normal or rearranged products are formed, depending on the nature of the 3-substituent.Bei der FIscHER'schen Indolsynthese werden aus Phenylhydrazonen von Aldehyden oder Ketonen je nach Substitution der Carbonylverbindung Indole oder auch
Regiospecific reduction of 1,3,3-trisubstituted succinimides by diborane
SummaryIt is possible to reduce 1,3,3-trisubstituted succinimides regiospecifically by diborane at the less substituted carbonyl group to yield the corresponding lactams. This method was used specially for the reduction of 2,8-diazaspiro [4,5] Weitere Literatur uber selektive Reduktionen von Succinimiden siehe [5]
ZusammenfassungDas p-Tolylhydrazon der (p-(n)-Butylpheny1)-glyoxylsaure (I) wurde durch Verteilungschromatographie auf Papier, sowie praparativ durch fraktionierte Kristallisation und Isomerisierung in die beiden syn-anti-isomeren Formen I11 (anti) und I V (syn) getrennt. Diese Konfigurationm wurde I den beiden Isomeren auf Grund von Smp., Loslichkeit, UV.-und 1R.-Spektren und pK'-Werten zugeordnet.Wisscnschaftliclie Abteilung der HACO A G., Gumligen
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