Water → HCID 86638791, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[4-(4-azido phenyl)-3-cyano-5,5-dimethyl-5H-furan-2-ylidene]malononitrile (100 mg, 0.33 mmol) and phenylacetylene (40 mg, 0.40 mmol) in 15 mL ethanol was stirred at 50° C. under N2. Sodium ascorbate (20 mg, 0.10 mmol in 2 mL water) solution was added followed by copper sulfate (12 mg, 0.048 mmol, 2 mL water) solution and stirred at 50° C. for 24 h. The reaction mixture was cooled, poured into cold water (100 mL) and was stirred at room temperature for 1 h. The precipitate formed was filtered off and air-dried. The crude product was further purified by recrystallization from EAC/1-propanol. Yield: 70 mg (52%) mp: 280° C. IR (neat) 3097, 2232, 1645, 1530 cm−1; 1H NMR (400 MHz, DMSO) δ 9.46 (s, 1H), 8.24 (d, J=8.8 Hz, 2H), 8.06 (d, J=8.8 Hz, 1H), 7.95-7.97 (m, 3H), 7.41-7.54 (m, 3H), 1.80 (s, 6H); 13CNMR (DMSO) δ 176.68, 176.52, 149.83, 147.27, 139.40, 130.17, 129.45, 128.86, 128.08, 126.9, 125.20, 120.34, 111.88, 111.00, 110.58, 103.71, 100.49, 54.80, 24.40; Anal. Calcd for C24H16N6O: C, 71.28; H, 3.99; N, 20.78. Found: C, 71.58; H, 3.84; N, 20.64. UV-Vis (CH2Cl2): λmax=369 nm, ε=2.05×104 L·mol−1 cm−1.

Provenance & Evidence