A Practical Preparation of 7-Methoxy-3(2H)-Benzofuranone

Novel Radioiodinated Aurones as Probes for SPECT Imaging of β-Amyloid Plaques in the Brain

“…Postmortem brain tissues from an autopsy-confirmed case of AD (73-year-old male) and a control subject (36-year-old male) were obtained from BioChain Institute Inc. The presence and localization of plaques on the sections were confirmed with immunohistochemical staining using a monoclonal Aβ antibody BC05 (Wako) as reported (23). The sections were incubated with [ 125 I]15 (120000 cpm/100 µL) for 1 h at room temperature.…”

“…The target aurone derivatives (9, 14, 15, 16, and 17) were prepared as shown in Schemes 1-3. The synthesis of h i b i t e d .the aurone backbone was achieved by an Aldol reaction of benzofuranones with benzaldehydes using Al 2 O 3(23). In this process, benzofuranones were reacted with methoxy benzaldehyde or hydroxy benzaldehyde in the presence of Al 2 O 3 in chloroform at room temperature to form compounds 5 and 14 in yields of 85.7% and 87.0%, respectively.Compound 5 was converted to 6 by demethylation with BBr 3 in CH 2 Cl 2 (5.2% yields).…”

Development of Dual-Acting Benzofurans for Thromboxane A2 Receptor Antagonist and Prostacyclin Receptor Agonist: Synthesis, Structure−Activity Relationship, and Evaluation of Benzofuran Derivatives

“…The preparation of compounds 8a-c is described in Scheme 2. We began the synthesis from 7-methoxy-2H-benzofuran-3one (19), which was easily prepared by the procedure of Bryant. 19 Thus, compound 19 was treated with lithium chloromethylene to obtain compound 20 in 10% yield.…”

“…We began the synthesis from 7-methoxy-2H-benzofuran-3one (19), which was easily prepared by the procedure of Bryant. 19 Thus, compound 19 was treated with lithium chloromethylene to obtain compound 20 in 10% yield. The low yield occurred because the carbonyl group of 19 was easily enolized upon treatment with base, and compound 19 was subject to intermolecular aldol condensation.…”

“…(7-Methoxybenzofuran-3-yl)acetic Acid Methyl Ester (24). To a solution of 7-mehtoxy-3(2H)-benzofuranone (19) (1.80 g, 11.0 mmol) in xylene (40 mL) was added Ph 3PCHCOOMe (4.10 g, 12.3 mmol), and the mixture was stirred at 140 °C for 18 h. The reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (AcOEt/n-hexane ) 1/3) to afford 24 (1.11 g, 46%).…”