Substituted 2-Phenoxypropionic and -butyric Acids and Derivatives

α2-Adrenoreceptors Profile Modulation. 2. Biphenyline Analogues as Tools for Selective Activation of the α2C-Subtype

“…)ethyl]-4,5-dihydrothiazole (25). A stirred solution of 2-(biphenyl-2-yloxy)propionic acid 41 (2.15 g, 8.89 mmol), 2-aminoethanethiol (0.683 g, 8.89 mmol), triphenylphosphine (6.97 g, 26.57 mmol), triethylamine (2.7 g, 26.57 mmol), and CCl4 (13.8 g, 88.9 mmol) in CH3CN (30 mL) was heated at 40 °C for 4 h. The solvent was removed under reduced pressure to give a residue that was taken up in AcOEt. The insoluble solid was filtered and washed with AcOEt.…”

“…)ethyl]-4,5-dihydrooxazole (24). 2-(Biphenyl-2-yloxy)propionic acid 41 (2.78 g, 11.47 mmol) was dissolved in dry CH2Cl2 under nitrogen atmosphere. After addition of oxalyl chloride (1.51 mL, 16.6 mmol) the mixture was stirred at room temperature for 2 days.…”

“…Imidazolines 8 and 26 were obtained from 2-(2-thiophen-3-yl-phenoxy)- ( 46 ) and 2-(biphenyl-2-yloxy)propionic acid methyl ester 36 by treatment with ethylenediamine in the presence of trimethylaluminum or by treatment with 1-vinyl-2-pyrrolidinone in the presence of NaH, respectively. Reaction of 2-(biphenyl-2-yloxy)propionic acid with 2-aminoethanethiol in the presence of triphenylphosphine provided compound 25 , and that with ethanolamine in the presence of oxalyl chloride and triethylamine yielded compound 24 (Scheme ).

2

…”