Tetrahedron p. 5909 - 5922 (1999)
Update date:2022-08-04
Topics:
Rezessy, Bela
Zubovics, Zoltan
Kovacs, Jozsef
Toth, Gabor
The reaction of 1,2,4-triazepine-3-thiones (13) with 2-haloketones afforded thiazolo[3,2-b][1,2,4]triazepines (14) selectively. The same bicycles were obtained by reaction of the chalcones 11 with 3-amino-2-imino- 4-R-thiazolines. On the other hand, condensation of the chalcones 11 with 2- hydrazino-4-R-thiazoles led to the hydrazones 17 which upon treatment with acid underwent ring closure to yield the non-condensed bicyclic isomers of 14 i.e. the dihydropyrazolyl thiazoles 18. The elucidation of structures and stereochemistry was achieved by comprehensive one- and two-dimensional NMR spectroscopy.
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Doi:10.1016/S0040-4020(99)00529-3
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