Premium
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)