Issue 0, 1979

Studies on keten and its derivatives. Part 88. Ethyl 5-oxo-4-oxaspi ro[2,3]hexane-1-carboxylate : synthesis and reactions

Abstract

Photoreaction of diketen with ethyl diazoacetate gave ethyl cis- and trans-5-oxo-4-oxaspiro[2,3]hexane-carboxylate (1). Ethanolysis of compound (1) with hydrogen chloride at room temperature gave diethyl 3-oxohexane-1,6-dioate (4). Heating of compound (1) with sodium hydroxide in ethanol gave 5-ethoxycarbonyl-4-oxopentanoic acid (5). Reaction of (1) with phenols gave the coumarin derivatives (7a and b). Reaction of (1) with anilines gave the 5-carbamoyl-4-oxopentanoate derivatives (2c and d). Compound (1) reacted with phenylhydrazine, hydroxylamine, and acetamidine to give the pyrazolone (10), isoxazolone (11), and pyrimidone derivative (12), respectively.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1979, 525-528

Studies on keten and its derivatives. Part 88. Ethyl 5-oxo-4-oxaspi ro[2,3]hexane-1-carboxylate : synthesis and reactions

T. Kato, N. Katagiri and R. Sato, J. Chem. Soc., Perkin Trans. 1, 1979, 525 DOI: 10.1039/P19790000525

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