Monocyclic 1,2,3‐Triazin‐4(3 H )‐ones: Synthesis, Structure and Photochemical Behaviour | Zendy

Celli Angela Maria | Zendy; Ferrini Serena | Zendy; Ponticelli Fabio | Zendy

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Monocyclic 1,2,3‐Triazin‐4(3 H )‐ones: Synthesis, Structure and Photochemical Behaviour

Author(s) -

Celli Angela Maria,

Ferrini Serena,

Ponticelli Fabio

Publication year - 2006

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200600119

Subject(s) - chemistry , pyrazolones , sodium borohydride , alkyl , dehydrogenation , medicinal chemistry , stereochemistry , organic chemistry , catalysis

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, 69451 Weinheim, Germany, 2006)

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