Synthesis of azepinoquinazoloncs from 2-methyl-3-(o-tolyl)-4-quinazolone

Some new azepinoquinazolones were synthesized from 2-methyl-3(o-tolyl)-4(3H)quinazolone (metliaqualone )as potential hypnotic agents. Methaqualone (I) reacted with dimethyl acetylene-dicarboxylate (dmad) to give the azepinoquinazolone (II) which on treatment with PPA gave the pentacyclic ketone (V). Subsequent sodium borohydride reduction of the ketone (V) gave the fused azepine (VIa). Reaction of the azepinoquinazolone (II) with formic acid resulted in cleavage of the quinazolone nucleus to give the azepine (VIII). None of the compounds synthesized exhibited significant hypnotic activity.     

Untersuchungen zum Einfluss der Stereochemie auf die Elektronenstossinduzierte ‘Retro-Diels-Alder’-Reaktion

The investigation of suitable model compounds shows that it is impossible to generalise about the mechanisms of the electron-impact-induced ‘Retro-Diels-Alder’ reaction on the basis of stereochemical effects.     

Investigations on the formation of 4-aminobicyclo[2.2.2]-octanones

Benzylidene acetone reacts with thiocyanates derived from secondary amines in a one-pot reaction to give 4-aminobicyclo[2.2.2]octan-2-ones. The reaction mixture was investigated for the presence of possible intermediates using GC-MS. These intermediates - diketones and enamines - were prepared and exposed to the same reaction conditions to examine the reaction mechanism. The reaction of ethyl styryl ketone with thiocyanates of secondary amines yielded cyclohexanone derivatives instead of the expected bicyclo- octanones. Their structures were established by means of a single crystal structure analysis.     

Incorporation and manipulation of coronene in an organic template structure

A two-dimensional molecular template structure of 1,3,5-benzenetricarboxylic acid (trimesic acid, TMA) was formed on a highly oriented pyrolytic graphite surface (HOPG) by self-assembly at the liquid-solid interface. Scanning tunneling microscopy (STM) investigations show high-resolution images of the porous structure on the surface. After the host structure was created, coronene molecules were inserted as guest molecules into the pores. STM results indicate that some of the guest molecules rotate inside their molecular bearing. Further investigations show that single coronene molecules can be directly kicked out of their pores by means of STM.     

Fuzzy quantum spaces and compatibility

Using ideas from fuzzy set theory, we generalize the notion of a quantum (probability) space introduced by Suppes to so-called fuzzy quantum spaces and we study the compatibility problem.     

Massenspektrometrische Untersuchung von Amiden. IV—Nachbargruppenbeteiligung Bei der Elektronensto-Ssinduzierten Fragmentierung von O-Nitrobenzoesaurepiperidid

The differences in the electron-impact-induced fragmentation of ortho and para- nitrobenzoylpiperidine are connected with neighbouring group participation of the NO₂ group. New oxygen migration, as well as the formation of stabilised radicals by intramolecular interaction of both functions, are only possible with the ortho compound.