Beilstein J. Org. Chem.2020,16, 190–199, doi:10.3762/bjoc.16.22
Vuyisa Mzozoyana Fanie R. van Heerden Craig Grimmer School of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X01, Scottsville, 3209, Pietermaritzburg, South Africa 10.3762/bjoc.16.22 Abstract 4-(2-Fluorophenyl)-7-methoxycoumarin (6) was synthesized by Pechmannreaction under mild
: DFT; F···H hydrogen bond; fluorinated phenylcoumarin; Pechmannreaction; through-space coupling; Introduction
Coumarins constitute one of the big classes of naturally occurring compounds. The first coumarin was isolated from the tonka bean (Dipteryx odorata) in 1820 and, to date, more than 1300
chloride (1) to yield methyl 2-fluorobenzoylacetate (3) [38][39]. These reactions are very rare in the literature, however, there are similar reactions for the synthesis of β-keto esters as reported by Sijbesma et al. [40] and Anwar [41]. The second step of the synthesis was the Pechmannreaction, commonly
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Graphical Abstract
Scheme 1:
Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin (6).