Some common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, molecular formula is C12H6N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C12H6N2O
To a three-necked round bottom flask were added 5,5′-(9,9′-spirobi[fluorene]-20,7-diyl)bis(4-(2-ethylhexyl)thiophene-2-carbaldehyde) (205 mg, 0.27 mmol), 1,1-dicyanomethylene-3-indanone (430 mg, 2.2 mmol), chloroform (50 mL), and 0.9 mLpyridine. The mixture was deoxygenated with nitrogen for 30 minand then refluxed for 12 h. After cooling down to room temperature,the mixture was poured into methanol (200 mL) and filtered.The residue was purified by column chromatography on silica gelusing petroleum ether/dichloromethane (1:1) as eluent yield anorange solid (207 mg, 69%). 1H NMR (400 MHz, CDCl3): delta 8.77 (s,2H), 8.68 (d, J 6.9 Hz, 2H), 7.96 (s, 1H), 7.93 (d, J 2.7 Hz, 2H), 7.89(d, J 4.8 Hz, 2H), 7.86 (d, J 1.8 Hz, 1H), 7.76 (m, 4H), 7.61 (d,J 5.4 Hz, 4H), 7.45 (t, J 7.5 Hz, 2H), 7.21 (t, J 7.5 Hz, 2H), 6.92 (s,2H), 6.82 (d, J 7.5 Hz, 2H), 2.39 (d, J 6.9 Hz, 4H),1.42 (m, 2H),1.09(m, 16H), 0.75 (m, 6H), 0.59 (t, J 6.9 Hz, 6H). 13C NMR (100 MHz,CDCl3): delta 188.63, 161.13, 157.22, 149.46, 149.27, 148.30, 143.36,141.49, 141.22, 140.47, 138.67, 137.35, 135.67, 135.47, 135.10, 133.58,130.17, 129.32, 128.84, 125.88, 125.17, 124.72, 124.37, 123.20, 121.23,121.15, 115.08, 114.99, 70.28, 66.57, 40.64, 32.95, 32.60, 28.90, 25.88,23.49, 14.65, 10.92. MS (MALDI): m/z calcd for C75H60N4O2S2 H:1114.4; found: 1114.1. Anal. Calcd for C75H60N4O2S2: C, 80.90; H,5.43; N, 5.03. Found: C, 80.77; H, 5.58; N, 5.33.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1080-74-6, its application will become more common.
Reference:
Article; Wang, Jiayu; Dai, Shuixing; Yao, Yuehan; Cheng, Pei; Lin, Yuze; Zhan, Xiaowei; Dyes and Pigments; vol. 123; (2015); p. 16 – 25;,
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