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Synthesis 2001(16): 2427-2430
DOI: 10.1055/s-2001-18721
DOI: 10.1055/s-2001-18721
PAPER
© Georg Thieme Verlag Stuttgart · New YorkSynthesis and Properties of O-Vinylamidoximes
Further Information
Received
21 August 2001
Publication Date:
05 August 2004 (online)
Publication History
Publication Date:
05 August 2004 (online)
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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