REACTION OF 1-ALPHA-ETHYL-1-BETA-(MESYLOX 6,7,12,12B-BETA-OCTAHYDRO-INDOLO[2,3-A]QUINOLIZINE WITH N-NUCLEOPHILES, S-NUCLEOPHILES AND AMBINENT NUCLEOPHILES

Some years ago Prof. Szantay's research group discovered the favourabl e vasodiloator and angioprotective activities of (-)-1 (Vintoperol). T he aim of these theses was the investigation of the nucleophilic subst itution reactions of the racemic hydroxymethyl compound 1 (see in the Hungarian text). Its mesylate ester was reacted with several primary a mines and secondary amino derivatives 2 were prepared, which intramole cular Mannich-reaction gave 15-aza-E-homoeburnane derivatives 3. Some interesting unexpected ring-transformations were observed in the case of certain aromatic amines. In the second part of the work the racemic hydroxymethyl compound was converted to its mercapto derivative (4) i n various ways. The reaction of the mesylate ester of 1 with ambident nucleophiles yielded several products. When it was made react with thi ocyanate, three products (5, 6 and 7) were obtained. he thiocyanato de rivative 5 and the imino-homo-thiaeburnane 6 were reduced to the thiol 4. In an independent way, the aza-homo-eburnane derivative 8, the str uctural isomer of 6 was also synthesized.