Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
On the Reactions of Oxazolium Salts with Dialkyl Acylphosphonates. A Novel Synthesis of 1, 4-Oxazin-3-one and Azetidin-2-one Derivatives
高見沢 映佐藤 久夫
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1974 年 22 巻 7 号 p. 1526-1541

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Reaction of Oxazolium salts (IX) with dialkyl acylphosphonates (IV) in the presence of triethylamine afforded 1, 4-oxazin-3-one (XII) and/or azetidin-2-one derivatives (XIII). In the reaction of IXa-b with IVa, stable reaction intermediates (Xa-b) were isolated. Some of the products were confirmed to be identical with authentic samples synthesized by an independent pathway. The mechanism of this novel reaction involving ring expansion and ring contraction, substituent effects on the reactivity, and stereochemistry of XIII are discussed.
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© The Pharmaceutical Society of Japan
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