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Synthesis 2001(16): 2427-2430
DOI: 10.1055/s-2001-18721
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Properties of O-Vinylamidoximes

Boris A. Trofimov*a, Elena Yu. Schmidta, Alexander M. Vasil’tsova, Al’bina I. Mikhalevaa, Alexey B. Zaitseva, Ludmila V. Morozovaa, Alexander G. Gorshkova, Jochem Henkelmannb, Jan-Dirk Arndtb
a A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation
Fax: +7(395)2396046; e-Mail: bat@irioch.irk.ru;
b BASF AG, Ammoniaklaboratorium ZAR/C-M 311, 67056 Ludwigshafen, Germany
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Publication History

Received 21 August 2001
Publication Date:
05 August 2004 (online)

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Abstract

O-Vinylamidoximes 2 are synthesized from amidoximes 1 and acetylene in superbase systems (KOH/DMSO, KOH/NMP, NaOH/CsF/NMP) in a preparative yield of up to 80%. They decompose explosively above 150 °C, being resistant to solvolysis in the KOH/DMSO system (100 °C, 3 h) and to polymerization (AIBN, UV). Trifluoroacetylation of O-vinylbenzamidoxime 2b with (CF3CO)2O/pyridine gives 5-trifluoromethyl-3-phenyl-1,2,4-oxadiazole (3) in 49% yield.

Key words

O-vinylamidoximes - amidoximes - acetylene - heterocycle - superbase - vinylation - trifluoroacetylation

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