(untitled) - Qian, Q; Tan, Y; Zhao, B; Feng, T; Shen, Q; Yao, Y
Org. Lett. 2014, 16 4516.m-Terphenyls 3a–u; General Procedure A mixture of the appropriate α,β-unsaturated carbonyl compound (1.0 mmol) and β-enaminone (1.5 mmol) with I2 (10 mol%) and elemental sulfur (1.0 equiv) in a reaction vial was stirred at 120 °C until the reaction was complete (TLC). H2O was then added and the mixture was extracted with EtOAc. The extracts were washed with brine, dried (Na2SO4), and concentrated under vacuum to give a crude product that was purified by column chromatography [silica gel, hexane–EtOAc (95:5)]. Ethyl 5′-(Butylamino)-4-methoxy-[1,1′:3′,1′′-terphenyl]-4′-carboxylate (3b) Yellow solid; yield: 330 mg (82%); mp 112–115 °C. 1H NMR (600 MHz, CDCl3): δ = 7.62–7.60 (m, 2 H), 7.44–7.41 (m, 2 H), 7.37–7.34 (m, 1 H), 7.26–7.25 (m, 1 H), 7.24–7.24 (m, 1 H), 6.91–6.89 (m, 2 H), 6.82–6.79 (m, 2 H), 6.38 (s, 1 H), 3.91 (q, J = 7.2 Hz, 2 H), 3.83 (s, 3 H), 3.23 (q, J = 7.2 Hz, 2 H), 1.69 (quin, J = 7.2 Hz, 2 H), 1.47 (sextet, J = 7.2 Hz, 2 H), 0.97 (t, J = 7.2 Hz, 3 H), 0.77 (t, J = 7.2 Hz, 3 H). 13C NMR (150 MHz, CDCl3): δ = 170.2, 158.8, 149.5, 144.8, 144.5, 141.2, 136.4, 129.2, 128.8, 127.9, 127.4, 117.5, 113.5, 112.3, 108.5, 60.4, 55.5, 43.3, 31.5, 20.4, 14.0, 13.5. HRMS (ESI): m/z [M + H]+ calcd for C26H30NO3: 404.21; found: 404.21. Ethyl 3-(Butylamino)-5-(1-naphthyl)biphenyl-2-carboxylate (3c) Yellow solid; yield: 313 mg (74%); mp 71–74 °C. 1H NMR (600 MHz, CDCl3): δ = 8.07 (s, 1 H), 7.90–7.85 (m, 3 H), 7.76 (dd, J = 1.8, 7.2 Hz, 1 H), 7.50–7.48 (m, 2 H), 7.37–7.32 (m, 5 H), 6.98 (d, J = 1.2 Hz, 1 H), 6.95 (d, J = 1.2 Hz, 1 H), 6.57 (br s, 1 H), 3.88 (q, J = 7.2 Hz, 2 H), 3.29 (q, J = 7.2 Hz, 2 H), 1.72 (quin, J = 7.2 Hz, 2 H), 1.50 (sextet, J = 7.2 Hz, 2 H), 0.989 (t, J = 7.2 Hz, 3 H), 0.699 (t, J = 7.2 Hz, 3 H). 13C NMR (150 MHz, CDCl3): δ = 170.1, 149.9, 145.3, 144.8, 144.1, 138.4, 133.7, 133.1, 128.5, 128.4, 128.1, 128.0, 127.8, 126.8, 126.5, 126.2, 125.6, 117.7, 111.9, 109.0, 60.4, 43.3, 31.5, 20.5, 14.1, 13.2. HRMS (ESI): m/z [M + H]+ calcd for C29H30NO2: 424.21; found: 424.21