α-Alkylmercapto- und α-Arylmercapto-alkylisocyanate

α-Alkylmercapto- and α-Arylmercapto-alkylisocyanates α-Alkylmercapto- and α-arylmercapto-alkylisocyanates 2 were prepared from α-halosulfides 1 by reaction with silver cyanate. With ammonia, primary or secondary amines they give the corresponding α-mercaptoalkyl-ureas 4 ; with alcohols, the α-mercaptoalkylurethans 3.     

Synthese und Antiserotoninaktivität einiger substituierter Tryptamine

Various N-substituted tryptamines are prepared by the oxalyl chloride method from 5-chloro- and 5-bromo-7-methylindole and 5-methyl-7-bromoindole. The antiserotonin activity of these substituted tryptamines on the isolated uterus of virgin rat is tested.     

Dimere Austauschprodukte aromatisch substituierter α-Aminonitrile VII. Mitt. über Umsetzungen von α-Aminonitrilen

Dimer Products of aromatic substituted Aminonitriles The dimer-products which in addition to hydrogen-exchange products are produced during the reaction of aromatic substituted aminonitriles with metallic sodium in toluene are unstable. The initially produced diphenyldiamine derivatives decompose during isolation under elimination of amine and then hydrolyse to form desoxybenzoin derivatives.     

Synthese substituierter 3-Adamantyloxocumarine unter Piperidinacetat/β-Alanin-Katalyse

Synthesis of Substituted 3-Adamantyloxocoumarines in the Presence of Piperidine acetate/β-Alanine The synthesis of the substituted 3-adamantyloxocoumarines 3a-h from the hydroxyaldehydes 1a-h by Knoevenagel reaction with 2 in the presence of piperidine acetate/β-alanine is described.     

Lactone, 10. Mitt. Zur Synthese N-heterocyclisch substituierter γ,γ-Diphenyl-γ-butyrolactone

Lactones, X: Synthesis of γ,γ-Diphenyl-γ-butyrolactones Substituted by N-Heterocycles Starting from 3 and 16 , syntheses of γ,γ-diphenyl-γ-butyrolactones with N-heterocycles at the α-position are described. Scope and limitation of the syntheses, tautomerism and stereochemistry of the products as well as spectroscopic results which are inconsistent with data from the literature are discussed.     

N-Glykoside und Glykamine von Cyclopentylamin, 1.2.3.4-Tetrahydro-1-naphthylamin und 5α-Cholestan-3β-amin

N-Glycosides and Glycamines of Cyclopentylamine, 1,2,3,4-Tetrahydro-1-naphthylamine and 5α-Cholestan-3β-amine The galactosyl-, mannosyl- and lactosyl-N-glycosides of cyclopentylamine and the galactosyl- and glucosyl-N-glycosides of the other two title compounds are described. All N-glycosides are reduced by cyanoborohydride to the corresponding glycamines.     

Synthese von γ,γ'-Dihydroxysulfonen und γ-Hydroxy-γ'-ketosulfonen

Syntheses of γ,γ'-Dihydroxysulfones and γ-Hydroxy-γ'-ketosulfones Reduction of γ,γ'-diketosulfones 1 with dimethylaminoborane leads to γ,γ'-dihydroxysulfones 3 via γ-hydroxy-γ'-ketosulfones 2 . The influence of substituents on the ratio of the yields of 2 and 3 is investigated.     

Neue Reaktionen an Phthalidisochinolinalkaloiden. Alkoxytauschreaktionen und Isomerisierungen an α- und β-Narcotin

New Reactions of Phthalidoisoquinoline Alkaloids. Alkoxy Exchange Reactions and Isomerisations of α- and β-Narcotine Substitution of the 7-methoxy group in α- and β-narcotine by other alkoxy groups occurs in an anhydrous ROH/RONa system. It is accompanied by isomerisation in position 3 with preference for the α-configuration (5R, 3S). In an alkaline aqueous system (ROH/KOH or 1N KOH only isomerisation in position 3 with preference for the β-configuration (5R, 3R) was observed. Some of the new 7-alkoxynarcotines were evaluated for their antitussive activity.     

Zur HPLC-Trennung einiger Mandelsäureesterderivate mittels α1-Glykoprotein (AGP)

HPLC-Separation of Some Mandelic Acid Ester Derivatives Using α₁-Acid Glycoprotein (AGP) Investigations on direct HPLC-resolution of the racemates of mandelic acid ester and phenylacetic acid ester derivatives using α₁-acid glycoprotein on silica (AGP) as the chiral stationary phase are described. The influence of various uncharged and charged modifiers (2-propanol, octanoic acid, N,N-dimethyloctylamine) in the mobile phase separately and in combination by variation of the pH-value was studied.     

α-Thiotetronsäuren, 1. Mitt.: Synthese und Eigenschaften von γ-Alkyliden-α-thiotetronsäuren

α-Thiotetronic Acids, I: Synthesis and Properties of γ-Alkylidene α-Thiotetronic Acids We report on the synthesis of the alkylidene α-thiotetronic acids 11 and 12a and a variety of their derivatives, starting with 2,3-dimethoxysuccinic thioanhydride ( 4 ) or diethyl 3-thioxoglutarate. The rhodium(II)-catalysed decomposition of the diazoketone 26 furnishes the reductone 12p and the aminoreductone 12r with the thietanone 27 as one of the by-products.     

Massenspektrometrische Untersuchungen an isomeren α,β- und β, γ-ungesättigten Ketonen mit raumerfüllenden Substituenten

A Mass Spectrometric Study on Isomeric α,β- and β,γ-Unsaturated Ketones with Bulky Substituents The mass spectra of the α,β- and β,γ-unsaturated ketones 1-4 (scheme 1) are very different depending on the stereochemistry of the double bond. The E-configurated ketone 2 predominantly shows McLafferty fragmentation, whereas Z-configurated ketone 1 reveals ?-cleavage. In the β, γ-unsaturated ketones 3 and 4, mainly loss of the pertinent allyl radical by α-cleavage was observed.     

Bis-thiolurethane aus α,ω-Alkandithiolen und Isocyanaten

Biscarbamothioates from α,ω-Alkanedithiols and Isocyanates Sixty biscarbamothioates 1 were prepared by triton-B catalyzed addition of α,ω-alkanedithiols to isocyanates. Some of the products were investigated for biological activity.     

Synthesen und Ringverengungsreaktionen α-halogenierter N-Phenylcamphersäureimide

Syntheses and Ringcontractions of β-Halo N-Phenylcamphoric Acid Imides By deprotonation and addition of electrophiles the N-phenylcamphoric acid imide 8 is transformed to the halo derivatives 3a–3c and to the deuterium labeled imide 3d . Under basic conditions 3b rearranges with ringcontraction to yield the bicyclic imido lacton 9a as a major product, whereas the regioisomer 4 is formed only in minor amounts.     

Darstellung und Reaktivität von α-Acyloxy-N-acylglycin-Derivaten

Synthesis and Reactivity of Derivatives of α-Acyloxy-N-acylglycine The N,O-Acylals 5–15 are obtainable from the chloro compounds 2 and carboxylic acids. Treatment of the electrophilic synthons with nucleophiles under basic conditions leads to products 16–19 by way of transamidoalkylation. A mechanism of the reaction is proposed.