Hetero Cope-Type Hydroamination of Hetero-Allenes with Oximes Having Olefin Moieties Leading to Nitrones, Causing
Yosuke Ide1, Naoto Matsuda1, Mei Osada1
1Showa Pharmaceutical University, 3-2-1 Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan.
Abstract:
Hetero-allenes such as isocyanates, isothiocyanates, and carbodiimides reacted with oxime having olefin moieties in the manner of hetero Cope-type hydroamination to generate N-modified nitrones, which underwent intramolecular cycloaddition to give intramolecular cycloadducts. Among them, the reaction of isocyanates with oximes proceeded at room temperature to provide the corresponding cycloadducts in very high yields. The efficiencies of these sequential cycloadditions were directly compared by competitive reactions. As a result, the order of reactivity to oxime 1a is isocyanate 2a, isothiocyanate 3a, and carbodiimide 6a. Theoretical studies were also conducted.
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