REDUCTIVE REARRANGEMENT OF 2-AROYL-2,3-DIHYDROBENZOFURANS INTO 2-HYDROXYDIHYDROCHALCONES AND FLAV-2-ENES

Authors

  • Дмитрий В. Осипов Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia
  • Максим Р. Демидов 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/10.1007/6473

Keywords:

2-aroyl-2, 3-dihydrobenzofurans, 4H-chromenes, flav-2-enes, 2-hydroxydihydrochalcones, o-quinone methides, samarium, zinc, reductive rearrangement.

Abstract

A two-step procedure was proposed for the synthesis of 2-aryl- and 2,4-diaryl-substituted 4H-chromenes by the formal [4+1] cycloaddition reaction of o-quinone methides and pyridinium ylides followed by reductive rearrangement of 2-aroyl-2,3-dihydrobenzofurans by the action of zinc in acetic acid or samarium and trimethylchlorosilane in 1,4-dioxane. The reduction of 3-unsubstituted 2aroyl-2,3-dihydrobenzofurans by the action of zinc in acetic acid leads mainly to 2-hydroxydihydrochalcones.

 

Author Biographies

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

к.х.н., доцент кафедры органической химии

Максим Р. Демидов, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia

к.х.н., доцент кафедры органической химии

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

д.х.н., профессор кафедры органической химии

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

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

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Published

2021-12-14

Issue

Vol. 57 No. 12 (2021)

Section

Original Papers