Tetrahedron p. 1791 - 1799 (1980)
Update date:2022-08-02
Topics:
Rudorf, W.-D.
The ketene S,S-acetals 1 readily react with aziridine to give the corresponding 3-(1-aziridinyl)-3-methylthio-acrylnitriles 2 and 3,3-bis-(1-aziridinyl)-acrylnitriles 3.Ketene S,N-acetals 4 yield 3-anilino-3-(1-aziridinyl)-acrylnitriles 5.Reaction of 5 with potassium iodide in acetone at room temperature leads to imidazolidines 8.The isomerisation is explained in terms of a two-step mechanism.The iodide ion-catalysed rearrangement was not successful when applied to 2a.Cyclisation of 5b in the presence of sodium hydride and following hydrolysis form the tautomeric quinolone 10.On contrary to 1 and 4 mercapto ethylenes 11 and 13 with aziridine give the thiazolidine 15.
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