The Synthesis of Hexahydrooxoepithiopyridinedicarboximides by the Reaction of Thioamides with N-substituted Maleimides

Article abstract of DOI:10.1002/jhet.5570350229

The synthesis of hexahydrooxoepithiopyridinedicarboxyimide (5: X₂ = N-Ph) by the reaction of thioamides 1 with N-substituted maleimide (2a) was examined. The reaction of primary thioamides, such as thiobenzamide and N-toluthioamide with N-phenylmaleimide gives compounds 5 together with corresponding 4-hydroxy-1,3-thiazoles 4, However, a similar reaction of secondary thioamides, such as N-methylthioacetamide, thiobenzanilide, with N-phenylmaleimide did not provide compounds 5 without addition of acid. The reaction pathway and the configuration of 5 were also investigated.