Collect. Czech. Chem. Commun. 1983, 48, 312-318

8-Substitution derivatives of D-6-methylergoline-I

Jiří Křepelka, Drahuše Vlčková, Jiří Holubek and Jiří Roubík

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


Reactions of esters I and II with methylsulphinylmethylsodium in dimethyl sulphoxide afforded β-keto sulphoxides III and IV, which were converted either into compounds V and VI under the conditions of the Pummerer rearrangement, or into ketones VII and VIII by the action of aluminium amalgam in 1,2-dimethoxyethane. Reduction of the compounds III and V with sodium borohydride produced β-hydroxy sulphoxide IX and dihydroxy derivative X respectively; the latter was characterised in the form of derivatives XI and XII. Condensation of the compound III with 1,2-diaminobenzene in acetic acid gave quinoxaline derivative XIII. The compounds prepared had no marked antilactation or antinidation activity.