COMPLEMENTARY COUPLING OF <i>o</i>-QUINONE METHIDES WITH 3-(<i>N,N</i>-DIETHYLAMINO)ACROLEIN – SYNTHESIS OF 1<i>H</i>-BENZO[<i>f</i>]CHROMENE-2-CARBALDEHYDES

Authors

  • Антон В. Лукашенко Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Виталий А. Осянин Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Дмитрий В. Осипов Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Юрий Н. Климочкин Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

DOI:

https://doi.org/10.1007/3346

Keywords:

1H-benzo[f]chromene-2-carbaldehydes, Mannich bases, о-quinone methides, cascade reactions, Diels–Alder reaction

Abstract

A series of 1H-benzo[f]chromene-2‑carbaldehydes was obtained from naphthol Mannich bases and 3-(N,N-diethylamino)acrolein via a cascade reaction comprising [4+2] cycloaddition of generated in situ 1,2-naphthoquinone-2-methides and a push-pull β-enaminoaldehyde with consecutive elimination of diethylamine.

Authors: Anton V. Lukashenko, Vitaly A. Osyanin*,
Dmitry V. Osipov, Yuri N. Klimochkin

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Published

2016-09-23

Issue

Vol. 52 No. 9 (2016): Pericyclic reactions in heterocyclic chemistry

Section

Original Papers