To a mixture of diketones 1 (0.3 g, 0.01mmol), Cinnamylideneacetophenones2 (0.220 g, 0.01mmol) and NaOEt (pinch sodium with 1 ml ethanol) were added. The reaction mixture was ground at room temperature until it became incompact solid. Then, the solid was heated in water-bath for 10 minutes at 90oC. The reaction was completed as shown by TLC. Then, the solid was treated with water and the water insoluble solid was separated and recrystalised in ethanol to provide styryl-cyclohexylderivatives3in good yield.
(3-Benzoyl-4-hydroxy-4,6-diphenyl-2-styryl-cyclohexyl)-phenyl-methanone 3a:white solid: 73%, 230oC1HNMR (CDCl3, 400 MHz):2.23–2.27 (d, 1H), 2.48–2.54 (t, 1H), 4.03–4.09 (m, 1H), 4.14–4.25 (m, 2H), 4.47–4.50 (d, 1H, J = 10.8Hz), 5.38 (s, OH), 6.69–6.73 (t, 1H), 6.81–6.85(t, 2H), 6.98–7.28(m, 17H), 7.54–7.55 (m, 6H), 7.94–7.95 (d, 1H, J = 7.6 Hz). 13CNMR (CDCl3, 100 MHz):43.4, 45.8, 48.1, 56.7, 56.7, 75.3, 124.8, 126.7, 126.9, 127.0, 127.4, 127.5, 127.6, 127.7, 128.0, 128.1, 128.2, 128.4, 128.6, 131.8, 132.7, 138.1, 138.6, 138.9, 142.1, 145.9, 203.6, 207.2 ppm.
[4-Hydroxy-3-(4-methyl-benzoyl)-4-phenyl-2-styryl-6-p-tolyl-cyclohexyl]-phenyl-methanone 3b: white solid: 79%, 242oC1HNMR (CDCl3, 400 MHz):1.91 (s, 3H), 2.12 (s, 3H),2.18–2.23 (dd, 1H), 2.43–2.49 (t, 1H), 3.97–4.20 (m, 3H), 4.43–4.46(d, 1H, J = 10.8Hz), 5.33 (s, OH), 6.60–6.62 (d, 2H, J = 10.8Hz), 6.87–6.89(d, 2H, J = 8Hz), 7.02–7.05(m, 6H), 7.13–7.26 (m, 13H), 7.51–7.53 (d, 2H, J = 7.6 Hz). 13CNMR (CDCl3, 100 MHz):20.7, 20.9,42.9, 46.0, 47.6, 57.0, 57.1, 75.4, 124.8, 126.9, 127.5, 127.6, 127.7, 127.8, 128.1, 128.6, 128.7, 128.9, 131.6, 132.5, 135.6, 136.1, 136.3, 138.2, 139.1, 145.9, 203.8, 207.4 ppm.
[3-Benzoyl-6-(3-chloro-phenyl)-4-hydroxy-4-phenyl-2-styryl-cyclohexyl]-phenyl-methanone 3c: white solid: 77%, 230oC1HNMR (CDCl3, 400 MHz):2.21–2.25 (t, 1H), 2.40–2.47 (t, 1H), 3.99–4.04 (t, 2H), 4.13–4.17(t, 1H), 4.44–4.47(d, 1H, J = 10.8Hz), 5.38 (s, OH), 6.67–6.69 (d, 2H, J = 7.6Hz), 6.73–6.78(t, 3H), 6.94–7.33(m, 18H), 7.54–7.55 (d, 3H, J = 7.6 Hz). 13CNMR (CDCl3, 100 MHz):43.1, 45.8, 47.7, 56.0, 56.2, 75.3, 124.7, 126.6, 126.9, 127.1, 127.2, 127.4, 127.7, 127.8, 127.9, 128.0, 128.3, 129.5, 129.7, 132.4, 133.1, 133.9, 134.2, 137.8, 138.5, 140.6, 143.9, 145.5, 202.6, 206.6 ppm.
(3-Benzoyl-4-hydroxy-2-styryl-4,6-di-p-tolyl-cyclohexyl)-phenyl-methanone 3d:white solid: 79%, 240oC1HNMR (CDCl3, 400 MHz):1.91 (s, 3H), 2.12 (s, 3H),2.18–2.23 (dd, 1H), 2.43–2.49 (t, 1H), 3.97–4.03 (t, 1H), 4.10–4.20 (m, 2H), 4.43–4.46 (d, 1H, J = 10.8Hz), 5.33 (s, OH), 6.60–6.62 (d, 2H, J = 7.6Hz), 6.87–6.89(d, 2H, J = 7.6Hz), 6.99–7.05(m, 10H), 7.13–7.26 (m, 9H), 7.51–7.53 (d, 2H, J = 7.6 Hz). 13CNMR (CDCl3, 100 MHz): 20.7, 20.9,42.9, 46.0, 47.6, 57.0, 57.1, 75.4, 124.8, 126.9, 127.5, 127.6, 127.7, 127.8, 128.1, 128.7, 128.9, 131.6, 132.5, 135.6, 136.1, 136.3, 138.2, 139.0, 139.1, 145.9, 203.8, 207.4 ppm.
[4-Hydroxy-3-(4-methyl-benzoyl)-6-phenyl-2-styryl-4-p-tolyl-cyclohexyl]-phenyl-methanone 3e:white solid: 80%, 236oC1HNMR (CDCl3, 400 MHz):2.19(s, CH3), 2.22(s, CH3),2.39–2.49 (q, 2H), 4.04–4.06 (d, 1H, J = 8.8Hz), 4.15–4.20 (t, 2H), 4.44–4.46 (d, 1H, J = 10.4Hz), 5.46 (s, OH), 6.70–6.72 (d, 1H, J = 6.8Hz), 6.80–6.85(q, 3H), 6.97–7.26(m, 18H), 7.41–7.43 (d, 2H, J = 8Hz), 7.53–7.54 (d, 1H, J = 7.2 Hz). 13CNMR (CDCl3, 100 MHz):20.8, 21.5,43.4, 46.2, 48.1, 56.1, 56.8, 75.3, 124.7, 124.8, 126.6, 126.8, 127.4, 127.5, 127.6, 128.0, 128.1, 128.2, 128.3, 128.4, 128.5, 128.8, 131.7, 135.6, 136.4, 138.7, 139.0, 142.2, 143.2, 143.6, 203.7, 206.5 ppm.
[4-(4-Chloro-phenyl)-4-hydroxy-3-(4-methyl-benzoyl)-2-styryl-6-p-tolyl-cyclohexyl]-phenyl-methanone 3f:white solid: 91%, 238oC1HNMR (CDCl3, 400 MHz):2.12(s, CH3), 2.20(s, CH3),2.26–2.33 (t, 1H), 2.39–2.45(t, 2H), 3.99–4.43(m, 3H), 5.33–5.42 (d, OH), 6.59–6.61(d, 1H, J = 8Hz), 6.83–6.88(m, 2H), 6.95–7.05(m, 12H), 7.12–7.22 (m, 7H), 7.39–7.41 (d, 1H, J = 6.8 Hz).7.51–7.53 (d, 1H, J = 6 Hz). 13CNMR (CDCl3, 100 MHz):20.8, 21.4,42.9, 44.9, 46.3, 47.6,56.3, 57.0, 75.3, 124.7, 124.8, 127.3, 127.4, 127.5,127.7, 127.8, 128.0, 128.2, 128.3,128.6, 128.7, 128.9, 129.2, 131.5,135.6, 136.0, 136.1,136.3, 136.4, 139.1, 139.2, 203.9, 206.2 ppm.
(3-Benzoyl-4-hydroxy-4-phenyl-2-styryl-6-p-tolyl-cyclohexyl)-p-tolyl-methanone3g:white solid: 95%, 245oC1HNMR (CDCl3, 400 MHz):2.13(s, CH3), 2.19(s, CH3),2.20–2.23(t, 1H), 2.43–2.49(t, 1H), 4.0-4.10(d, 1H, J = 12Hz), 4.09–4.17 (q, 2H), 4.43–4.46 (d, 1H, J = 12Hz), 5.33 (s, OH), 6.61–6.63(d, 2H, J = 8Hz), 6.88–6.90(d, 2H,J = 8Hz ), 7.02–7.09(m, 8 H), 7.13–7.23 (m, 11H), 7.51–7.53 (d, 2H, J = 8 Hz). 13CNMR (CDCl3, 100 MHz):20.6, 20.8,42.9, 44.3, 46.1,47.6, 57.0, 75.3, 124.8, 125.6, 126.9, 127.1, 127.4, 127.5, 127.7,127.8, 128.1, 128.5, 128.7, 129.0, 131.5, 132.5, 135.6, 136.1, 136.3, 138.2, 139.0, 145.9, 203.7, 207.3 ppm.