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

DOI:

https://doi.org/10.1007/5609

Keywords:

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

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.

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Published

2020-05-28

Issue

Vol. 56 No. 5 (2020)

Section

Original Papers