Regardless of the substantial desire for n. H-6), 7.40C6.99 (20H, m, aromatics), 4.93, 4.89 (2 1H, 2d, = 11.0 Hz in each, Ph= 10.8 Hz in each, Ph= 12.2 Hz in each, Ph= 11.3 Hz in each, Ph= 9.5 Hz, H-1), 3.94 (1H, pt, = buy BKM120 9.5, 9.2 Hz, Rabbit Polyclonal to HSP90B (phospho-Ser254) H-3 or H-4), 3.85 (1H, pt, = 9.4, 9.3 Hz, H-2 or H-3 or H-4), 3.84 (1H, pt, = 9.5, 9.3 buy BKM120 Hz, H-2 or H-3 or H-4), 3.79 (1H, dd, = 11.9, 5.2 Hz, H-6a), 3.64 buy BKM120 (1H, dd, = buy BKM120 11.9, 1.9 Hz, H-6b), 3.52-3.49 (1H, m, H-5); 13C NMR (100 MHz, CDCl3) (ppm): 168.8, 163.3 (C-2, C-4), 160.5 (C-6), 138.3, 138.1, 137.7, 136.9, 129.0C127.9 (aromatics), 114.8 ((10b) and (10c). The title compounds were prepared from compound 1 (400 mg, 0.66 mmol) and ethyl 2-cyano-3-ethoxyacrylate 4 (224 mg, 1.33 mmol) according to general procedure 1. Reaction time: 1 h. Purification by column chromatography (EtOAc-hexane = 1:3) yielded 10b as the 1st and 10c as the second fraction. 10b: Yield: 167 mg (37%), colourless syrup. Rf = 0.25 (EtOAc-hexane = 1:2); []D = +54 (c 0.20, CH2Cl2); 1H NMR (400 MHz, CDCl3) (ppm): 8.81 (1H, s, H-6), 7.84 (1H, br s, NH2), 7.31C6.97 (20H, m, aromatics), 6.38 (1H, br s, NH2), 4.93, 4.89 (2 1H, 2d, = 11.2 Hz in each, PhCH2), 4.84, 4.57 (2 1H, 2d, = 10.7 Hz in each, PhCH2), 4.60, 4.27 (2 1H, 2d, = 11.4 Hz in each, PhCH2), 4.60, 4.27 (2 1H, 2d, = 12.2 Hz in each, PhCH2), 4.36 (2H, q, i = 7.2 Hz, CH2CH3), 4.36 (1H, d, = 9.6 Hz, H-1), 4.03 (1H, pt, = 9.6, 9.0 Hz, H-2), 3.84 (1H, pt, = 9.2, 9.0 Hz, H-3), 3.76C3.3.71 (3H, m, H-4, H-6a, H-6b), 3.65 (1H, ddd, = 9.5, 4.5, 2.2 Hz, H-5), 1.40 (3H, t, = 7.2 Hz, CH2CH3); 13C NMR (100 MHz, CDCl3) (ppm): 168.9, 166.0, 162.8 (C-2, C-4, COOEt), 159.6 (C-6), 138.8, 138.2, 138.2, 138.1, 128.5C127.5 (aromatics), 104.3 (C-5), 87.1, 82.9, 81.3, 79.8, 77.3 (C-1CC-5), 75.7, 75.2, 74.8, 73.5 (4 PhCH2), 69.1 (C-6), 61.3 (CH2CH3), 14.4 (CH2CH3). ESI-MS positive mode (= 11.3 Hz in each, PhCH2), 4.86, 4.60 (2 1H, 2d, = 10.8 Hz in each, PhCH2), 4.71, 4.46 (2 1H, 2d, = 11.5 Hz in each, PhCH2), 4.54, 4.48 (2 1H, 2d, = 12.0 Hz in each, PhCH2), 4.37 (1H, d, = 9.5 Hz, H-1), 3.86-3.70 (6H, m, H-2CH-6a,b); 13C NMR (100 MHz, CDCl3) (ppm): 162.9, 160.0 (C-2, C-6), 161.1 (C-4), 138.1, 137.9, 137.6, 137.1, 128.7C127.9 (aromatics), 113.3 (CN), 103.2 (C-5), 85.8, 79.2, 78.9, 78.2, 77.7 (C-1CC-5), 75.6, 75.2, 74.6, 73.4 (4 PhCH2), 69.0 (C-6). ESI-MS buy BKM120 positive mode ((10d). Prepared from compound 1 (400 mg, 0.66 mmol) and diethyl 2-(ethoxymethylene)malonate 5 (265 L, 1.33 mmol) according to general procedure 1. Reaction time: 1 h. Purified by column chromatography (EtOAc-hexane 1:1) to give 367 mg (80%) colourless syrup. Rf = 0.21 (EtOAc-hexane = 1:1); []D = +9 (c 0.50, CH2Cl2); 1H NMR (400 MHz, CDCl3) (ppm): 11.35 (1H, br s, NH), 8.55 (1H, s, H-4), 7.32C7.11 (20H, m, aromatics), 4.88, 4.84 (2 1H, 2d, = 11.2 Hz in each, Ph= 10.9 Hz in each, Ph= 11.4 Hz in each, Ph= 12.1 Hz in each, Ph= 7.2 Hz, = 9.5 Hz, H-1), 3.86C3.65 (6H, m, H-2CH-6a,b), 1.38 (3H, t, = 7.2 Hz, CH2(10e). Prepared from compound 1 (400 mg, 0.66 mmol) and 2-benzylidenemalononitrile 6 (204 mg, 1.33 mmol) according to general procedure 1. Reaction time: 1 h. The title compound precipitated from your reaction combination was a pale yellow amorphous solid. Yield: 373 mg (78%). Rf = 0.41 (EtOAc-hexane = 2:3); []D = ?12 (c 0.27, CH2Cl2); 1H NMR (400.