The Journal of Organic Chemistry

The Vilsmeier-Haack reaction of isoxazolin-5-ones. Synthesis and reactivity of 2-(dialkylamino)-1, 3-oxazin-6-ones

EM Beccalli, A Marchesini

Index: Beccalli, Egle M.; Marchesini, Alessandro Journal of Organic Chemistry, 1987 , vol. 52, # 15 p. 3426 - 3434

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Citation Number: 22

Abstract

The Vilsmeier-Haack reaction on isoxazolin-5-ones gives 2-(dialkylamino)-l, 3-oxazin-6- ones, and a reaction path is proposed depending on substitution pattern of the isoxazolin-5- ones studied. A thermal equilibrium between the oxazinones, imino ketenes, and vinyl isocyanates is hypothesized to explain most of the chemical reactivity of the 2-(dialkylamino)- 1, 3-oxazin-6-ones.