Design, Synthesis and Pharmacological Tests - Dissertation Example

Chemical shifts are reported in parts per million (ppm) relative to TMS and the coupling constants (J) are described in hertz. IR spectrums were obtained using Perkin Elmer Spectrum 100 FT-IR spectrometer, wavenumbers (?) in cm-1 Methods 1. Preparation of (Z)-(((5-(2-bromo-2-nitrovinyl)-1,3-phenylene)bis(oxy))bis (methylene))dibenzene (43) Scheme 26 Synthesis of (E)-(((5-(2-nitrovinyl)-1,3-phenylene)bis(oxy))bis(methylene))dibenzene (43). In a 25 ml round bottom flask a solution of 3,5-dibenzyloxy-benzaldexyde (318.4 mg, 1.0 mmol) in xylene (mixture of isomers, 10 ml) were added bromonitromethane (279.

9 mg, 2 mmol), dimethylamine bromide (1.134 g, 9 mmol) and potassium fluoride (8.7 mg, 0.15 mmol). The flask was equipped with a Dean-Stark system and the mixture was heated at reflux temperature until the disappearance of the aryl-aldehyde by TLC (usually noted after a reaction time of 4-5 hours). Toluene (10 ml) was added and the reaction was left refluxing for 18 hours. After being cooled at room temperature, the reaction mixture was evaporated under vacuum to remove xylene, then diluted with water and extracted with CH2Cl2 (3? 20 mL). In some cases, a filtration over the Celite® surface was required to remove excess reagent residues before extraction.

The organic phase was then washed with water, dried over anhydrous MgSO4, filtered, and concentrated under a vacuum. The crude product was purified by chromatography on silica gel (40 g) using mixtures of Hexane and AcOEt of increased polarity. The target compound was afforded as a brown oil (45 mg, 10% yield) 2. Preparation of (E)-1-(benzyloxy)-4-(2-nitrovinyl)benzene (50) Scheme 27 Synthesis of (E)-1-(benzyloxy)-4-(2-nitrovinyl)benzene (50). In around 250 ml bottom flask, a solution of 4-bezyloxybenzaldehyde (6.36 g, 0.03 mmol) in toluene (75 ml) was prepared.

To this solution, nitromethane (17.7 ml, 0.33 mol), dimethylamine hydrobromide (15.108 g, 0.12 mmol), and potassium fluoride (341.5 mg, 4.5 mmol) was added. The flask was equipped with a Dean-Stark system and the mixture was heated at reflux temperature until the disappearance of the aryl-aldehyde by TLC.