Turkish Journal of Chemistry
DOI
10.55730/1300-0527.3625
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.
Keywords
Metal-carbenoid, diazocarbonyl, dihydrofuran, insertion, heteroaryl
First Page
1429
Last Page
1437
Recommended Citation
EROĞLU, KUMSAL; ANAÇ, OLCAY; and KIŞKAN, FÜSUN ŞEYMA
(2023)
"Comparison of metal-carbenoid reactions of β-2-five-membered heteroaryl substituted α,β-unsaturated ketones,"
Turkish Journal of Chemistry: Vol. 47:
No.
6, Article 12.
https://doi.org/10.55730/1300-0527.3625
Available at:
https://journals.tubitak.gov.tr/chem/vol47/iss6/12
