Two-Step Synthesis of 1,3-Oxazin-6-One Derivatives Involving N-Selective Alkenylation of Isoxazol-5-Ones Using
Yuta Iino1, Yasuyuki Matsushima1, Kosuke Nakashima1
1Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Abstract:
A highly regioselective N-alkenylation of isoxazol-5-ones using β-phenylsulfonylenones as alkenyl donors quickly afforded N-alkenylisoxazol-5-one derivatives in excellent yield. Subsequent treatment of these derivatives with 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) generated 1,3-oxazin-6-one derivatives in high yield. To our knowledge, this report is the first report to successfully synthesize 1,3-oxazin-5-one derivatives via N-selective alkenylation of isoxazol-5-one derivatives and subsequent transformation of the resulting N-alkenylisoxazol-5-ones.
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