Oxidation of the easily available 1-(alkylamino)pyrazolones allows the preparation of the title compounds, which are a new class of heterocycles, in good yields. The structure of these compounds is assigned on the basis of HR mass spectroscopy and sodium borohydride reduction to (Z,E)-2-methyl-3-phenyl-N- (1-phenylethyl)acrylamide. Ring contraction/rearrangement to 2-alkyl-2H-1,2,3-triazole is observed under UV irradiation. A possible mechanistic rationalisation of the observed processes is proposed. © Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Celli, A.M., Ferrini, S., Ponticelli, F. (2006). Monocyclic 1,2,3-Triazin-4(3H)-ones: Synthesis, Structure and Photochemical Behaviour. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(13), 3021-3025 [10.1002/ejoc.200600119].
Monocyclic 1,2,3-Triazin-4(3H)-ones: Synthesis, Structure and Photochemical Behaviour
Ponticelli, F.
2006-01-01
Abstract
Oxidation of the easily available 1-(alkylamino)pyrazolones allows the preparation of the title compounds, which are a new class of heterocycles, in good yields. The structure of these compounds is assigned on the basis of HR mass spectroscopy and sodium borohydride reduction to (Z,E)-2-methyl-3-phenyl-N- (1-phenylethyl)acrylamide. Ring contraction/rearrangement to 2-alkyl-2H-1,2,3-triazole is observed under UV irradiation. A possible mechanistic rationalisation of the observed processes is proposed. © Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
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https://hdl.handle.net/11365/17161
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