Comparison of metal-carbenoid reactions of β-2-five-membered heteroaryl substituted α, β-unsaturated ketones

Kumsal Eroǧlu*, Olcay Anaç, Füsun Şeyma Kişkan

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

In this study, β-2-heteroaryl substituted (N-methyl 2-pyrrolyl, 2-thiophenyl, 2-furyl) α,β-unsaturated ketones were reacted with two α-diazo carbonyl compounds that had different characteristics (dimethyl diazo malonate and 1-diazo-1-phenyl-propane-2-one) in the presence of both copper and rhodium catalysts. In the case of reactions with N-methyl 2-pyrrolyl α,β-unsaturated ketones, the major product was the insertion derivative. However, in the reactions of 2-thiophenyl and 2-furyl α,β-unsaturated ketones with dimethyl diazomalonate (acceptor-acceptor disubstituted), only dihydrofuran products were formed over carbonyl ylides. When 2-thiophenyl and 2-furyl α,β-unsaturated ketones were reacted with 1-diazo-1-phenyl-propane-2-one (donor-acceptor disubstituted), 1-phenylpropane-1,2-dione was obtained under our reaction conditions.

Original languageEnglish
Pages (from-to)1429-1437
Number of pages9
JournalTurkish Journal of Chemistry
Volume47
Issue number6
DOIs
Publication statusPublished - 2023

Bibliographical note

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Keywords

  • Metal-carbenoid
  • diazocarbonyl
  • dihydrofuran
  • heteroaryl
  • insertion

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