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Note | Regular issue | Vol 55, No. 10, 2001, pp.1963-1969
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9297
Synthesis of 1,2,4-Oxadiazolylimidazo[1,5-a]thieno[2,3-e]pyrazines as Ligands for the γ-Aminobutyric Acid A/Benzodiazepine Receptor Complex

Thomas Erker* and Karin Trinkl

*Institute of Pharmaceutical Chemistry, University of Vienna, Pharmaziezentrum, Althanstrsse 14, A-1090 Vienna, Austria


Starting from 5-benzoyl-2-chloro-3-nitrothiophene the thieno[2,3-b]pyrazine-2,3-dione ring system (4) was synthesized. This compound was reacted with potassium tert-butoxide and diethyl chlorophosphate to give diethyl 7-benzoyl-4-isopropyl-3-oxo-3,4-dihydrothieno[2,3-b]pyrazin-2-ylphosphate (5), which gave with the desired 5-alkyl-3-isocyanomethyl-1,2,4-oxadiazoles in the presence of additional potassium tert-butoxide the 1,2,4-oxadiazolylimidazo[1,5-a]thieno[2,3-e]pyrazine derivatives (6-10) as ligands for the γ-aminobutyric acid A / benzodiaz-epine receptor complex.