Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
On the Reactions of 1, 3, 4-Oxadiazolium Salts with Dialkyl Acylphosphonates. A Novel Synthesis of 1, 3, 4-Oxadiazin-5-one Derivatives
AKIRA TAKAMIZAWAHISAO SATO
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1975 Volume 23 Issue 5 Pages 948-954

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Abstract
Reaction of 3-ethyl-5-aryl-1, 3, 4-oxadiazolium salts (X) with dialkyl acylphosphonates (V) in the presence of triethylamine afforded 2-aryl-4-ethyl-6-alkyl (or aryl)-5, 6-dihydro-4H-1, 3, 4-oxadiazin-5-one derivatives (XII) via an acyclic intermediate (XI) which is a 1 : 1 adduct of X and V. The mechanism of this novel reaction involving ring expansion is discussed briefly.
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© The Pharmaceutical Society of Japan
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