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The reactions between bisimidoyl chlorides of oxalic acid 1 and different thioamides derived from CH-acidic methylene compounds 2, 7 as well as thiobiuretes 9-11 were investigated. The hitherto unknown cyclic keten-N,S-acetals 3 with an oxalic acid substructure were mainly formed by an ambidoselective cycloacylation reaction. Comparison of  13 C NMR data suggests a thiazolidine structure with three exocyclic doubly bound residues. In the case of compound 3 g the exact configuration (Z) was determinated on the basis of a heteronuclear Overhauser experiment.

zeitschrift für naturforschung b

Regioselektive Cyclisierung von Thiocarbonsäureamiden mit Bisimidoyl- chloriden -Synthese von Thiazolidinen mit einer Ketenacetal-Substruktur / Regioselective Cyclization of Thiocarboxylic Amides with Bisimidoyl Chlorides - Synthesis of Thiadiazolidines Containing a Ketenacetal Substructure