A SYNTHESIS OF CARBONYL-SUBSTITUTED 4-ARYL-4<i>H</i>-BENZO[<i>h</i>]CHROMENES BASED ON A THREE-COMPONENT CONDENSATION OF α-NAPHTHOL, AROMATIC ALDEHYDES, AND β-ENAMINONES

Authors

  • Ирина А. Семенова 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/10.1007/6918

Keywords:

aromatic aldehydes, 4-aryl-4H-benzo[h]chromenes, α-naphthol, 1, 2-naphthoquinone-2-methides, push-pull olefins, Diels–Alder reaction, three-component reactions

Abstract

A three-component condensation of α-naphthol, aromatic aldehydes, and β-enaminones in acetic acid under reflux led to β-carbonylsubstituted (with respect to the pyran oxygen atom) 4-aryl-4H-benzo[h]chromenes. The reaction is a cascade process involving the generation of 1,2-naphthoquinone-2-methide, the Diels–Alder reaction involving push-pull β-enaminone, and the subsequent elimination of a secondary amine.

Authors: Irina А. Semenova, Vitaly А. Osyanin*, Dmitry V. Osipov*, Yuri N. Klimochkin

Author Biographies

Ирина А. Семенова, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

аспирант кафедры органической химии

Виталий А. Осянин, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

д.х.н., профессор кафедры органической химии

Дмитрий В. Осипов, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

к. х. н., доцент кафедры органической химии

Юрий Н. Климочкин, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

д.х.н., профессор, заведующий кафедрой органической химии

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Published

2022-11-17

Issue

Vol. 58 No. 11 (2022)

Section

Short Communications