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Benzyl (3S,4E)-4-[(dimethylamino)methylidene]-5-oxotetrahydrofuran-3-ylcarbamate 5 was prepared in 4 steps from L-aspartic acid 1. Acid-catalysed treatment of 5 with amines 6 gave the dimethylamine substitution products 7. Benzyl (3S,4E)-4-[(arylamino)methylidene]-5oxotetrahydrofuran-3-ylcarbamates 7c–n were prepared by parallel solution phase synthesis from 5 and anilines 6c–n in 45–94% yields. Enaminone 5 reacted with potassium cyanide in the presence of 18-crown-6 to afford benzyl 4-cyanomethyl-5-oxo-2,5-dihydrofuran-3-ylcarbamate 9. Upon reaction of 9 with nitrile oxide 10 the 1,2,4-oxadiazole derivative 11 was isolated in poor yield, while treatment of 9 with diazomethane 12 furnished the methylation products 13 and 14.

Parallel solution phase synthesis of benzyl (3S,4E)-4-[(arylamino)methylidene]-5-oxotetrahydrofuran-3-ylcarbamates