Synthesis, spectroscopic and antibacterial investigations of new hydroxy ethers and heterocyclic coumarin derivatives

Abstract

O OH O N N R a: R=H b: R=Ph O OH O O OH O O NMe 2 NH 2 NHR Toluene 6a-bThe reactions between oligoethylene glycol diglycidyl ethers 2a-c with both 7-hydroxy-4-methyl-2Hchromen-2-one and 4-hydroxy-2H-chromen-2-one lead to new hydroxy ethers 3 and 4 containing coumarin moieties in good yield. The synthesis of 3-(3-(dimethylamino)acryloyl)-4-hydroxy-2H-chromen-2-one 5 and new heterocyclic compounds 4-hydroxy-3-(1H-pyrazol-3-yl)-2H-chromen-2-one 6a, 4-hydroxy-3-(1-phenylpyrazol-3-yl)-2H-chromen-2-one 6b and 4-hydroxy-3-(isoxazol-3-yl)-2H-chromen-2-one 6c is also described. All compounds were characterized by 1 H NMR, 13 C{ 1 H} NMR, 2D-1 H-13 C HMBC, 2D-1 H NOESY NMR, IR, and MS spectroscopy. Additionally, the antibacterial activity of the new products containing coumarin moiety was evaluated. This activity is clearly dependent on the chemical structure of compounds.

Expedious synthesis for α, β-unsaturated coumarin derivatives using boran chelates: A novel class of potential antibacterial and antioxidant agents

“…In the course of our continuous interest on the synthesis of coumarin derivatives including 4-hydroxyl coumarin with antibacterial and antioxidant activities [24,25], we have extended our research to the synthesis and biological evaluation of new coumarinyl chalcones using 3-acetyl-4-difluoro boryloxycoumarin coumarin (2) via an easy, efficient and quit method.…”

3-Acetyl-4-hydroxycoumarin: Synthesis, reactions and applications

“…Moreover, several reports on synthetic routes for 3-acetyl-4-hydroxycoumarin 1 have been published during the last decade via the reaction of 2 with acetic acid or acetic anhydride 4 in the presence of phosphorous oxychloride as a catalyst (Sukdolak et al, 2004;Li et al, 2012a;Traven et al, 2000;Lyssenko and Antipin, 2013;Mulwad and Hegde, 2009;Hamdi et al, 2008;Eisenhauer and Link, 1953;Klosa, 1955;Ukita et al, 1950;Dholakia et al, 1968) (Scheme 2).…”

“…In a similar manner, the reaction of 3-acetyl-4-hydroxycoumarin 1 with an excess of N,N-dimethyl formamide dimethyl acetal (DMF-DMA) 29 Hamdi et al, 2008;Siddiqui and Farooq, 2012;Ahmed and Siddiqui, 2013 afforded the corresponding 3-(3-(dimethylaminoacryloyl)-3-acetyl-4-hydroxycoumarin 30 (Scheme 20). Synthesis of 3-Acetyl-4-hydroxycoumarin…”

Recent advances in 4-hydroxycoumarin chemistry. Part 1: Synthesis and reactions

“…The synthesis of the podands 180 could be achieved via the base-catalyzed reaction of 2 equivalents of 4-hydroxycoumarin 1 with oligoethylene glycol diglycidyl ether 179 in refluxing methanol afforded directly the expected coumarin hydroxy ether in good yield (Hamdi et al, 2008a;Li et al, 2012) …”