Darstellung cyclischer Hydraziniumdithiokohlensäurediester-Salze sowie deren Umsetzung mit C- und N-Nucleophilen

Synthesis of Cyclic Hydraziniumdithiocarbonic Acid Diester Salts and their Chemical Reaction with C- and N-Nucleophiles The aim of this dissertation was the synthesis of novel hydraziniumdithiocarbonic acid ester salts via cyclic dithiocarbazic acid esters. To get new insights into the synthetic potential of these reactive intermediates a considerable number of tests have been carried out. Certain dithiocarbazic acid esters have shown a variety of biological activities, e.g. fungitoxical and antibiotic potency respectively. Modification of cyclic dithiocarbazic acid derivatives like 3-amino-2-thioxo-tetrahydro-1,3-thiazine-4-ones and 3-amino-4-tert-butyl-3H-thiazole-2-thiones in position 2 leads to products with potential pharmacological activities. In order to carry out these modifications it was necessary to activate the molecules mentioned above. Methylation of the exocyclic sulphur of the 2-thioxo-thiazines and 2-thioxo-3H-thiazoles leads to reactive hydrazinium salts. The electrophilic carbon center reacts with simple, phenylogous and vinylogous C- and N-nucleophiles like malononitrile, acetonitrile derivatives, acetic acid ester derivatives, 2-cyanobutenenitriles, benzenesulfonamides and 3-amino-2-cyanophenylacrylonitriles. By reaction with similar strong C- and N-nucleophiles the hydrazinium salts have been converted into a considerable number of condensated products. Some interesting side reaction products hava been isolated.