Synthesis of aryl substituted 2,4,5,6-tetrahydro-3H-1,2,4-triazepine-3-thiones/ones starting from chalcone-derived β-isothiocyanato ketones
2016
Fesenko, Anastasia A. | Grigoriev, Mikhail S. | Shutalev, Anatoly D.
A general two-step synthesis of 7-aryl substituted 2,4,5,6-tetrahydro-3H-1,2,4-triazepine-3-thiones from 1-aryl-3-isothiocyanatopropan-1-ones has been developed. The synthesis involved reaction of these isothiocyanato ketones with hydrazines followed by acid-catalyzed heterocyclization of the prepared 4-(3-oxopropyl)thiosemicarbazides or their hydrazones. Triazepine-3-thiones were converted into their 3-oxo analogs by oxidation with H2O2 under basic conditions. Conformations of the obtained triazepine-3-thiones/ones in DMSO solution and in solid state were established using 1H NMR spectroscopy and single crystal X-ray diffraction.
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