Turkish Journal of Chemistry
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.
DOI
10.55730/1300-0527.3625
Keywords
Metal-carbenoid, diazocarbonyl, dihydrofuran, insertion, heteroaryl
First Page
1429
Last Page
1437
Recommended Citation
EROĞLU, K, ANAÇ, O, & KIŞKAN, F. Ş (2023). Comparison of metal-carbenoid reactions of β-2-five-membered heteroaryl substituted α,β-unsaturated ketones. Turkish Journal of Chemistry 47 (6): 1429-1437. https://doi.org/10.55730/1300-0527.3625
