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α-FUNCTIONALIZED KETENE N,S-ACETALS AS TWO-CARBON SYNTHONS IN THE REACTION WITH 1,2-NAPHTHOQUINONE 1-METHIDE. SYNTHESIS OF 3-AMINO-1H-BENZO[f]CHROMENES

Антон В. Лукашенко, Дмитрий В. Осипов, Виталий А. Осянин, Юрий Н. Климочкин
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Abstract


A series of 3-amino-1H-benzo[f]chromenes were obtained in the reaction of 1-[(dimethylamino)methyl]naphthalen-2-ol with push-pull ketene N,S-acetals containing an electron-withdrawing group in the α-position. It is assumed that the reaction proceeds as a [4+2] cycloaddition of ketene N,S-acetals to in situ generated 1,2-naphthoquinone 1-methide. Quantum-chemical methods were used to study the synchronicity of the Diels–Alder reaction.

Keywords


3-amino-1H-benzo[f]chromene; ketene N,S-acetals; 1,2-naphthoquinone 1-methide; push-pull olefin; Diels–Alder reaction.

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