α-FUNCTIONALIZED KETENE <i>N</i>,<i>S</i>-ACETALS AS TWO-CARBON SYNTHONS IN THE REACTION WITH 1,2-NAPHTHOQUINONE 1-METHIDE. SYNTHESIS OF 3-AMINO-1<i>H</i>-BENZO[<i>f</i>]CHROMENES
Authors
Антон В. Лукашенко
Samara State Technical University,
244 Molodogvardeyskaya St., Samara 443100, Russia
Дмитрий В. Осипов
Samara State Technical University,
244 Molodogvardeyskaya St., Samara 443100, Russia
Виталий А. Осянин
Samara State Technical University,
244 Molodogvardeyskaya St., Samara 443100, Russia
Юрий Н. Климочкин
Samara State Technical University,
244 Molodogvardeyskaya St., Samara 443100, Russia
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.