Water → HCID 86638792, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-[4-(4-azidophenyl)-3-cyano-5,5-dimethyl-5H-furan-2-ylidene]malononitrile (60 mg, 0.20 mmol) and diethyl-(4-ethynyl-phenyl) amine (35 mg, 0.20 mmol) in ethanol (10 mL) was stirred at 60° C. Sodium ascorbate (14 mg, 0.07 mmol in 1 mL water) solution was added followed by copper sulfate (8 mg, 0.03 mmol in 1 mL water) solution. The mixture was stirred at 60° C. for 24 h, cooled, poured into cold water and was stirred at room temperature for 1 h. The precipitate formed was filtered off and air dried. The product was further purified by silica gel column chromatography using hexane/EAC 30-50% and finally recrystallized from dichloromethane/methanol. Yield: 70 mg (73%) Mp: 275° C. IR (neat) 3022, 2230, 1620 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.09 (s, 1H), 8.05 (d, J=8.8 Hz, 2H), 7.93 (d, J=8.8 Hz, 2H), 7.72 (d, J=8.8 Hz, 2H), 6.73 (d, J=8.8 Hz, 2H), 3.40 (q, 4H), 1.83 (s, 6H), 1.18 (t, 6.8 Hz, 6H); 13CNMR (CDCl3) δ 175.44, 174.40, 149.64, 147.93, 140.30, 129.83, 128.81, 126.91, 126.14, 120.32, 115.77, 114.36, 110.77, 110.79, 109.99, 102.25, 98.91, 59.89, 44.11, 26.07, 12.30. Anal. Calcd for C28H25N7O: C, 70.72; H, 5.30; N, 20.62. Found: C, 69.83; H, 5.63; N, 20.87. UV-Vis (CH2Cl2): λmax=319 nm ε=3.562×104 L·mol−1 cm−1.

Provenance & Evidence