Synthesis and electrochemical study of new 3-(hydroxyphenyl)benzo[f]coumarins

Abstract

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Palladium-Catalyzed Weakly Coordinating Lactone-Directed C–H Bond Functionalization of 3-Arylcoumarins: Synthesis of Bioactive Coumestan Derivatives

“…The title compound 8i was synthesized following method D. The crude product was purified by using 2.0:8.0 ethyl acetate/hexane as an eluent: R f = 0.4; white solid (63.5 mg, 96%); mp = 213-215 °C (lit . mp 216–217 °C); 1 H NMR (400 MHz, CDCl 3 ) δ 8.75 (s, 1H), 8.37 (d, J = 8.4 Hz, 1H), 8.09 (d, J = 8.8 Hz, 1H), 7.99 (d, J = 8.0 Hz, 1H), 7.86 (s, 1H), 7.84–7.74 (m, 1H), 7.68–7.64 (m, 1H), 7.60 (d, J = 9.2 Hz, 1H), 7.46–7.41 (m, 2H), 7.15–7.09 (m, 2H); 13 C­{ 1 H} NMR (100 MHz, CDCl 3 ) δ 163.3, 155.3, 153.0, 139.7, 133.7, 131.1, 130.8, 130.6, 129.2, 129.0, 128.6, 126.6, 126.4, 123.6, 121.6, 121.5, 119.7, 116.5, 114.0; HRMS (ESI) m / z [M + H] + calcd for C 19 H 13 O 3 + 289.0859, found 289.0844.…”

“…29 f ]chromen-3-one (8i). 33 The title compound 8i was synthesized following method D. The crude product was purified by using 2.0:8.0 ethyl acetate/hexane as an eluent: R f = 0.4; white solid (63.5 mg, 96%); mp = 213-215 °C (lit. 33 Method E).…”

“…33 The title compound 8i was synthesized following method D. The crude product was purified by using 2.0:8.0 ethyl acetate/hexane as an eluent: R f = 0.4; white solid (63.5 mg, 96%); mp = 213-215 °C (lit. 33 Method E). An oven-dried 10 mL round-bottom flask was charged with 3-(2-hydroxyphenyl)-2H-chromen-2-one 8a (0.21 mmol, 50 mg), DDQ (0.42 mmol, 95 mg), and toluene (2 mL).…”

Fragmentation pathways of synthetic and naturally occurring coumarin derivatives by ion trap and quadrupole time‐of‐flight mass spectrometry

“…In addition, many molecules based on the coumarin ring system have been synthesized owing to their wide range of biological activities, including anticoagulant, antineurodegenerative, anticancer, antioxidant, antibacterial, and antifungal properties . Increasing numbers of coumarin derivatives are being isolated and synthesized, widening the structural diversity of this class of compounds.…”

Arylation of Carbonyl Compounds via Photoredox Catalysis

“…The 3-arylcoumarins can be synthetized in two different approaches. The first one is based on building the coumarin scaffold already having the aryl group present at the starting materials through condensation reactions, such as Pechmann 204,205 , Perkin 157,[206][207][208][209][210] or Knoevenagel 211,212 , catalyzed condensation by N-heterocyclic carbenes, carbonylative annulation between phenols and alkynes 213 and mediated synthesis by cyanuric chloride 214 .…”