Supporting Information

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1 Supporting Information Visible-Light-Photocatalyzed Synthesis of Phenanthridinones and Quinolinones via Direct Oxidative C H Amidation Yonghoon Moon, a,b Eunyoung Jang, a,b Soyeon Choi, a,b and Sungwoo Hong*,b,a a Department of Chemistry, Korea Advance Institute of Science and Technology (KAIST), Daejeon , Korea b Center for Catalytic Hydrocarbon Functionalization Institute for Basic Science (IBS), Daejeon, , Korea I. General Methods and Materials S2 II. Optimization Study S2 III. Stern-Volmer Quenching Experiments S4 IV. Experimental Procedure S9 V. Compound Charicterization S9 Appendix I Spectral Copies of 1H- and 13C- NMR Data Obtained in this Study S25

2 I. General Methods and Materials Unless stated otherwise, reactions were performed in flame-dried glassware. Analytical thin layer chromatography (TLC) was performed on precoated silica gel 60 F 254 plates and visualization on TLC was achieved by UV light (254 and 365 nm). Flash column chromatography was undertaken on silica gel ( mesh). 1 H NMR was recorded on 600 MHz and chemical shifts were quoted in parts per million (ppm) referenced to the appropriate solvent peak or 0.0 ppm for tetramethylsilane. The following abbreviations were used to describe peak splitting patterns when appropriate: br = broad, s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, dd = doublet of doublet, td = doublet of triplet, ddd = doublet of doublet of doublet. Coupling constants, J, were reported in hertz unit (Hz). 13 C NMR was recorded on 150 MHz and was fully decoupled by broad band proton decoupling. Chemical shifts were reported in ppm referenced to the center line of a triplet at 77.0 ppm of CDCl 3. Mass spectral data were obtained from the KAIST Basic Science Institute by using ESI method. Commercial grade reagents and solvents were used without further purification except as indicated below. Infrared (IR) spectra were acquired on Bruker Alpha-E FT-IR Spectrometer. Frequencies are given in wave numbers (cm -1 ) and only selected peaks were reported. Stern-Volmer experiments were conducted on a Shimadzu RF-6000 Spectro Fluorophotometer and the solution were irradiated at 420 nm and luminescence was measured at 497 nm. II. Optimization Study Table S1. Optimization study of phenanthridinone derivatives. [a] Entry Photocatalyst (2.5 mol%) Base (0.5 equiv) Solvent Temp. ( o C) Yield [%] [b] 1 [c][d] [Ir(dFCF 3 ppy) 2 bpy]pf 6 NMeBu 3 OP(O)(OBu) 2 1,2-DCE [Ir(dFCF 3 ppy) 2 bpy]pf 6 NMeBu 3 OP(O)(OBu) 2 1,2-DCE Ru(bpy) 3 (PF 6 ) 2 NMeBu 3 OP(O)(OBu) 2 1,2-DCE 25 N.R. 4 Ir(ppy) 3 NMeBu 3 OP(O)(OBu) 2 1,2-DCE 25 N.R. 5 Eosin Y NMeBu 3 OP(O)(OBu) 2 1,2-DCE 25 N.R.

3 6 [Ir(dFCF 3 ppy) 2 bpy]pf 6 NMeBu 3 OP(O)(OBu) 2 MeCN [Ir(dFCF 3 ppy) 2 bpy]pf 6 NMeBu 3 OP(O)(OBu) 2 DMSO [Ir(dFCF 3 ppy) 2 bpy]pf 6 NMeBu 3 OP(O)(OBu) 2 Dioxane [Ir(dFCF 3 ppy) 2 bpy]pf 6 NMeBu 3 OP(O)(OBu) 2 1,2-DCE [Ir(dFCF 3 ppy) 2 bpy]pf 6 NMeBu 3 OP(O)(OBu) 2 1,2-DCE [e] [Ir(dFCF 3 ppy) 2 bpy]pf 6 NMeBu 3 OP(O)(OBu) 2 1,2-DCE [e] [Ir(dFCF 3 ppy) 2 bpy]pf 6-1,2-DCE [Ir(dFCF 3 ppy) 2 bpy]pf 6 K 3 PO 4 1,2-DCE [Ir(dFCF 3 ppy) 2 bpy]pf 6 NBu 4 OP(O)(OBu) 2 1,2-DCE [Ir(dFCF 3 ppy) 2 bpy]pf 6 NaHCO 3 1,2-DCE [Ir(dFCF 3 ppy) 2 bpy]pf 6-1,2-DCE [Ir(dFCF 3 ppy) 2 bpy]pf 6 TFA 1,2-DCE [f] [Ir(dFCF 3 ppy) 2 bpy]pf 6 NMeBu 3 OP(O)(OBu) 2 1,2-DCE 60 N.R NMeBu 3 OP(O)(OBu) 2 1,2-DCE 60 N.R. 20 [c] [Ir(dFCF 3 ppy) 2 bpy]pf 6 NMeBu 3 OP(O)(OBu) 2 1,2-DCE 60 N.R. [a] Reactions were performed using 1a (0.1 mmol, 1.0 equiv), photocatalyst (0.025 equiv), base (0.5 equiv) and 1,2-dichloroethane (3.0 ml) under air balloon for 20 h with light irradiation using a 14 W Blue LED. [b] Yield was determined by 1H NMR. N.R. = no reaction

4 Intensity (a.u.) III. Stern-Volmer Quenching Experiments no 1a 3mM 1a 6mM 1a 9mM 1a 12mM 1a wavelength (nm) Figure S1. Quenching of the Ir(dFCF 3 ppy) 2 (bpy)pf 6 emission (0.3 mm in 1,2-dichloroethane) in the presence of NMeBu 3 OP(O)(OBu) 2 (1.5 mm in 1,2-dichloroethane) and increasing amounts of amide (1a) at room temperature.

5 Intensity (a.u.) no 1a 3mM 1a 6mM 1a 9mM 1a 12mM 1a wavelength (nm) Figure S2. Quenching of the Ir(dFCF 3 ppy) 2 (bpy)pf 6 emission (0.3 mm in 1,2-dichloroethane) in the presence of increasing amounts of amide (1a) at room temperature.

6 Intensity (a.u.) no 1a 24mM 1a 48mM 1a wavelength (nm) Figure S3. Quenching of the Ir(dFCF 3 ppy) 2 (bpy)pf 6 emission (0.3 mm in 1,2-dichloroethane) in the presence of increasing amounts of amide (1a) at 60 o C.

7 Intensity (a.u.) 4000 no 1a 24mM 1a 48mM 1a wavelength (nm) Figure S4. Quenching of the Ir(dFCF 3 ppy) 2 (bpy)pf 6 emission (0.3 mm in 1,2-dichloroethane) in the presence of hydrogen peroxide (2.0 mm in 1,2-dichloroethane), sodium hydroxide (1.5 mm in 1,2-dichloroethane) and increasing amounts of amide (1a) at 60 o C.

8 I o /I 1.6 with phosphate base at r.t. without phosphate base at r.t. with hydroperoxy anion at 60 o C without phosphate base at 60 o C a (mm) Figure S5. Stern-Volmer quenching plot. Figure S6. Monitoring isomerization progress starting from the E and Z isomers.

9 IV. Experimental Procedure General procedure for synthesis of phenanthridinone and quinolinone derivatives: Reactions were conducted in test tube (16 ml) sealed with rubber septa. N-phenyl-[1,1'-biphenyl]-2-carboxamide (1a) (27.3 mg, 0.1 mmol), Ir[(dFCF 3 ppy) 2 bpy)pf 6 (0.025 equiv), and NMeBu 3 OP(O)(OBu) 2 (0.5 equiv) were combined in anhydrous 1,2-dichloroethane (3.0 ml) with air balloon. The reaction mixture was stirred at 60 o C for h under 14 W Blue LED irradiation. The reaction mixture was monitored by TLC (using ethyl acetate : n- hexane = 1 : 5 as the mobile phase) and stirred until starting material disappeared. The crude mixture was extracted three times with dichloromethane and ammonium chloride solution, and washed with water and brine. The combined organic layer was dried over magnesium sulfate, and filtered. The resulting mixture was purified by flash column chromatography on silica gel (ethyl acetate : n-hexane = 1:5) to obtain the desired product compound 2a (81%, 21.9 mg) as a pale yellow solid. Gram scale procedure: Reactions were conducted in round-bottom-flask (250 ml) sealed with rubber septa. N-phenyl-[1,1'-biphenyl]-2- carboxamide (1a) (1.01 g, 3.66 mmol), Ir[(dFCF 3 ppy) 2 bpy]pf 6 (0.025 equiv), and NMeBu 3 OP(O)(OBu) 2 (0.5 equiv) were combined in anhydrous 1,2-dichloroethane (54.0 ml) with air balloon. The reaction mixture was stirred at 60 o C for 42 h under 14 W Blue LED irradiation. The reaction mixture was monitored by TLC (using ethyl acetate : n-hexane = 1 : 5 as the mobile phase) and stirred until starting material disappeared. The crude mixture was extracted three times with dichloromethane and ammonium chloride solution, and washed with water and brine. The combined organic layer was dried over magnesium sulfate, and filtered. The resulting mixture was purified by flash column chromatography on silica gel (ethyl acetate : n-hexane = 1 : 5) to afford the desired product compound 2a (74%, 725 mg) as a pale yellow solid. V. Compound Characterizations:

10 5-phenylphenanthridin-6(5H)-one (2a). From N-phenyl-[1,1'-biphenyl]-2-carboxamide (27.3 mg, 0.1 mmol), compound 2a (Yield 81% mg.) was obtained. Pale yellow solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.56 (d, J = 7.9 Hz, 1H), 8.32 (d, J = 8.3 Hz, 1H), 8.29 (dd, J = 7.6, 1.9 Hz, 1H), 7.80 (t, J = 7.7 Hz, 1H), (m, 3H), 7.53 (t, J = 7.5 Hz, 1H), 7.33 (d, J = 7.3 Hz, 2H), (m, 2H), 6.69 (dd, J = 7.7, 1.7 Hz, 1H). 13 C NMR (150 MHz, CDCl 3 ) δ 161.6, 139.1, 138.2, 134.0, 132.8, 130.1, 129.0, 129.0, 128.7, 128.1, 125.8, 122.9, 122.6, 121.7, 119.0, IR (cm -1 ) 3066, 2326, 1656, 1607, 1486, 1454, 1434, 1347, 1321, 747, 724, 697, 655. HRMS (ESI + ) m/z calcd. C 19 H 13 NNaO + [M+Na] + : , found: (4-methoxyphenyl)phenanthridin-6(5H)-one (2b). From N-(4-methoxyphenyl)-[1,1'-biphenyl]-2-carboxamide (30.3 mg, 0.1 mmol), compound 2b (Yield 82% mg.) was obtained. Yellow solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.56 (dd, J = 8.0, 1.5 Hz, 1H), 8.31 (d, J = 8.2 Hz, 1H), 8.28 (dd, J = 7.9, 1.7 Hz, 1H), 7.79 (td, J = 7.5, 1.5 Hz, 1H), 7.60 (t, J = 7.5 Hz, 1H), (m, 2H), 7.24 (d, J = 8.8 Hz, 2H), 7.11 (d, J = 8.8 Hz, 2H), 6.76 (dd, J = 8.2, 1.4 Hz, 1H), 3.89 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 161.9, 159.5, 139.4, 133.9, 132.7, 130.7, 129.9, 129.0, 129.0, 128.0, 125.8, 122.9, 122.5, 121.7, 119.0, 117.0, 115.4, IR (cm -1 ) 3072, 2369, 2328, 1657, 1608, 1511, 1436, 1317, 1249, 1032, 827, 751, 725, 654. HRMS (ESI + ) m/z calcd. C 20 H 15 NNaO + 2 [M+Na] + : , found: (p-tolyl)phenanthridin-6(5H)-one (2c). From N-(p-tolyl)-[1,1'-biphenyl]-2-carboxamide (28.7 mg, 0.1 mmol), compound 2c (Yield 78% mg.) was obtained. White solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.55 (dd, J = 8.0, 1.5 Hz, 1H), 8.32 (d, J = 8.2 Hz, 1H), 8.28 (dd, J = 7.7, 1.7 Hz, 1H), 7.79 (t, J = 7.6 Hz, 1H), 7.59 (t, J = 7.6 Hz, 1H), 7.40 (d, J = 7.8 Hz, 2H), (m, 2H), 7.20 (d, J = 7.8 Hz, 2H), 6.73 (dd, J = 8.0, 1.6 Hz, 1H), 2.47 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 161.8, 139.3, 138.7, 135.6, 134.0, 132.7, 130.8, 129.0, 128.7, 128.1, 125.9, 122.9, 122.5, 121.7, 119.0, 117.1, IR (cm -1 ) 3070, 2354, 2326, 2880, 1655, 1607, 1511, 1487,

11 1435, 1317, 1122, 812, 749, 725, 654, 519. HRMS (ESI + ) m/z calcd. C 20 H 15 NNaO + [M+Na] + : , found: (4-(tert-butyl)phenyl)phenanthridin-6(5H)-one (2d). From N-(4-(tert-butyl)phenyl)-[1,1'-biphenyl]-2- carboxamide (32.9 mg, 0.1 mmol), compound 2d (Yield 90% mg.) was obtained. White solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.56 (dd, J = 8.1, 1.3 Hz, 1H), 8.33 (d, J = 8.2 Hz, 1H), 8.30 (dd, J = 7.9, 1.6 Hz, 1H), 7.80 (ddd, J = 8.3, 7.1, 1.4 Hz, 1H), (m, 3H), (m, 2H), 7.24 (d, J = 8.3 Hz, 2H), 6.74 (dd, J = 8.2, 1.3 Hz, 1H), 1.41 (s, 9H). 13 C NMR (150 MHz, CDCl 3 ) δ 161.7, 151.6, 139.4, 135.5, 134.0, 132.7, 129.0, 128.4, 128.0, 127.1, 126.0, 122.9, 122.5, 121.7, 119.0, 117.2, 34.8, IR (cm -1 ) 3068, 2876, 2359, 2328, 1657, 1608, 1513, 1435, 1346, 1334, 1318, 1124, 1040, 825, 750, 725, 656, 563, 518. HRMS (ESI + ) m/z calcd. C 23 H 21 NNaO + [M+Na] + : , found: (m-tolyl)phenanthridin-6(5H)-one (2e). From N-(m-tolyl)-[1,1'-biphenyl]-2-carboxamide (28.7 mg, 0.1 mmol), compound 2e (Yield 81% mg.) was obtained. White solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.55 (dd, J = 8.0, 1.5 Hz, 1H), 8.32 (d, J = 8.3 Hz, 1H), 8.29 (dd, J = 7.7, 1.8 Hz, 1H), 7.80 (ddd, J = 8.4, 7.1, 1.5 Hz, 1H), 7.60 (t, J = 7.2 Hz, 1H), 7.48 (t, J = 7.7 Hz, 1H), 7.33 (d, J = 7.8 Hz, 1H), (m, 2H), (m, 2H), 6.71 (dd, J = 8.1, 1.6 Hz, 1H), 2.43 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 161.7, 140.3, 139.2, 138.2, 134.0, 132.7, 130.0, 129.6, 129.5, 129.0, 129.0, 128.1, 125.9, 125.9, 122.9, 122.6, 121.7, 119.0, 117.1, IR (cm -1 ) 3051, 2881, 2350, 2328, 1659, 1607, 1487, 1435, 1318, 1290, 1265, 1121, 1043, 781, 750, 725, 701, 647. HRMS (ESI + ) m/z calcd. C 20 H 15 NNaO + [M+Na] + : , found:

12 5-(o-tolyl)phenanthridin-6(5H)-one (2f). From N-(o-tolyl)-[1,1'-biphenyl]-2-carboxamide (28.7 mg, 0.1 mmol), compound 2f (Yield 85% mg.) was obtained. Pale yellow solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.57 (dd, J = 7.9, 1.8 Hz, 1H), 8.34 (d, J = 8.2 Hz, 1H), 8.31 (dd, J = 7.3, 2.0 Hz, 1H), 7.81 (ddd, J = 8.3, 7.0, 1.7 Hz, 1H), 7.61 (t, J = 7.5 Hz, 1H), (m, 3H), (m, 2H), 7.21 (dd, J = 7.3, 1.8 Hz, 1H), 6.59 (d, J = 6.7 Hz, 1H), 2.04 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 161.1, 138.4, 137.1, 136.5, 134.1, 132.8, 131.6, 129.4, 129.1, 128.9, 128.1, 127.8, 125.9, 123.1, 122.7, 121.8, 119.1, 116.4, IR (cm -1 ) 3073, 2887, 2357, 2320, 1657, 1608, 1488, 1435, 1318, 1289, 1267, 751, 725, 654. HRMS (ESI + ) m/z calcd. C 20 H 15 NNaO + [M+Na] + : , found: (4-bromophenyl)phenanthridin-6(5H)-one (2g). From N-(4-bromophenyl)-[1,1'-biphenyl]-2-carboxamide (35.2 mg, 0.1 mmol), compound 2g (Yield 70% mg.) was obtained. Pale yellow solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.53 (dd, J = 8.0, 1.4 Hz, 1H), 8.32 (d, J = 8.2 Hz, 1H), 8.29 (dd, J = 7.6, 1.9 Hz, 1H), 7.80 (ddd, J = 8.4, 7.1, 1.5 Hz, 1H), 7.73 (d, J = 8.5 Hz, 2H), 7.60 (t, J = 7.6 Hz, 1H), (m, 2H), 7.21 (d, J = 8.5 Hz, 2H), 6.68 (dd, J = 7.8, 1.7 Hz, 1H). 13 C NMR (150 MHz, CDCl 3 ) δ 161.6, 138.8, 137.3, 134.0, 133.5, 133.0, 130.9, 129.2, 129.0, 128.2, 125.7, 123.1, 122.9, 122.8, 121.8, 119.1, IR (cm -1 ) 3063, 2882, 2801, 2328, 2362, 1649, 1604, 1487, 1345, 1319, 1124, 1098, 1012, 816, 749, 725, 688, 650, 512. HRMS (ESI + ) m/z calcd. C 19 H 12 BrNNaO + [M+Na] + : , found:

13 5-(4-iodophenyl)phenanthridin-6(5H)-one (2h). From N-(4-iodophenyl)-[1,1'-biphenyl]-2-carboxamide (39.9 mg, 0.1 mmol), compound 2h (Yield 74% mg.) was obtained. Pale yellow solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.52 (dd, J = 8.0, 1.4 Hz, 1H), 8.32 (d, J = 8.2 Hz, 1H), 8.29 (dd, J = 7.6, 1.9 Hz, 1H), 7.93 (d, J = 8.4 Hz, 2H), 7.80 (ddd, J = 8.3, 7.2, 1.4 Hz, 1H), 7.60 (t, J = 7.5 Hz, 1H), (m, 2H), 7.08 (d, J = 8.4 Hz, 2H), 6.68 (dd, J = 7.9, 1.6 Hz, 1H). 13 C NMR (150 MHz, CDCl 3 ) δ 161.6, 139.5, 138.8, 138.0, 134.0, 133.0, 131.2, 129.2, 129.0, 128.2, 125.7, 123.1, 122.9, 121.8, 119.1, 116.8, IR (cm -1 ) 3057, 2887, 2357, 2328, 1650, 1605, 1487, 1457, 1320, 1264, 1126, 1101, 1013, 814, 746, 725, 706. HRMS (ESI + ) m/z calcd. C 19 H 12 INNaO + [M+Na] + : , found: methoxy-5-(4-methoxyphenyl)phenanthridin-6(5H)-one (2i). From 4'-methoxy-N-(4-methoxyphenyl)-[1,1'- biphenyl]-2-carboxamide (33.3 mg, 0.1 mmol), compound 2i (Yield 76% mg.) was obtained. Yellow solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.49 (dd, J = 8.0, 1.0 Hz, 1H), 8.18 (t, J = 8.1 Hz, 2H), 7.74 (ddd, J = 8.3, 7.2, 1.4 Hz, 1H), 7.51 (ddd, J = 8.1, 7.1, 1.1 Hz, 1H), 7.22 (d, J = 8.8 Hz, 2H), 7.09 (d, J = 8.8 Hz, 2H), 6.84 (dd, J = 8.8, 2.5 Hz, 1H), 6.22 (d, J = 2.5 Hz, 1H), 3.88 (s, 3H), 3.69 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 162.3, 160.3, 159.6, 141.0, 134.2, 132.8, 130.8, 129.9, 129.0, 127.0, 124.7, 124.4, 121.2, 115.5, 112.7, 109.3, 102.0, 55.5, IR (cm -1 ) 3008, 2887, 2357, 2326, 1659, 1611, 1584, 1508, 1455, 1348, 1320, 1291, 1245, 1220, 1179, 1027, 850, 822, 770, 717. HRMS (ESI + ) m/z calcd. C 21 H 17 NNaO + 3 [M+Na] + : , found:

14 5-(4-methoxyphenyl)-3-(trifluoromethyl)phenanthridin-6(5H)-one (2j). From N-(4-methoxyphenyl)-4'- (trifluoromethyl)-[1,1'-biphenyl]-2-carboxamide (37.1 mg, 0.1 mmol), compound 2j (Yield 58% mg.) was obtained. Pale yellow solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.56 (dd, J = 8.0, 1.4 Hz, 1H), 8.38 (d, J = 8.4 Hz, 1H), 8.34 (d, J = 8.1 Hz, 1H), 7.84 (ddd, J = 8.4, 7.2, 1.5 Hz, 1H), 7.67 (ddd, J = 8.1, 7.2, 1.1 Hz, 1H), 7.49 (dd, J = 8.2, 0.9 Hz, 1H), 7.22 (d, J = 8.8 Hz, 2H), 7.12 (d, J = 8.8 Hz, 2H), 6.99 (s, 1H), 3.90 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 161.8, 159.9, 139.6, 133.1, 132.8, (q, J = 32.7 Hz), 129.9, 129.8, 129.3, 126.5, 123.8, (q, J = Hz), 122.2, 121.7, (q, J = 3.6 Hz), 115.7, (q, J = 4.1 Hz), IR (cm -1 ) 3079, 2357, 2320, 2887, 1665, 1609, 1510, 1416, 1326, 1298, 1250, 1173, 1127, 1083, 1033, 820, 774, 727, 663, 538. HRMS (ESI + ) m/z calcd. C 21 H 14 F 3 NNaO + 2 [M+Na] + : , found: (tert-butyl)-5-(4-methoxyphenyl)phenanthridin-6(5H)-one (2k). From 4'-(tert-butyl)-N-(4-methoxyphenyl)- [1,1'-biphenyl]-2-carboxamide (35.9 mg, 0.1 mmol), compound 2k (Yield 80% mg.) was obtained. White solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.52 (dd, J = 7.9, 1.4 Hz, 1H), 8.28 (d, J = 8.1 Hz, 1H), 8.20 (d, J = 8.5 Hz, 1H), 7.77 (ddd, J = 8.4, 7.1, 1.5 Hz, 1H), 7.56 (ddd, J = 8.0, 7.1, 1.1 Hz, 1H), 7.31 (dd, J = 8.4, 1.9 Hz, 1H), 7.24 (d, J = 8.8 Hz, 2H), 7.11 (d, J = 8.8 Hz, 2H), 6.75 (d, J = 1.8 Hz, 1H), 3.90 (s, 3H), 1.19 (s, 9H). 13 C NMR (150 MHz, CDCl 3 ) δ 162.2, 159.5, 152.7, 139.4, 134.0, 132.7, 130.9, 130.0, 129.0, 127.6, 125.7, 122.6, 121.5, 120.1, 116.7, 115.4, 113.9, 55.5, 34.9, IR (cm -1 ) 3057, 2881, 2360, 2326, 1658, 1611, 1510, 1407, 1320, 1264, 1249, 1034, 826, 773, 729, 702. HRMS (ESI + ) m/z calcd. C 24 H 23 NNaO + 2 [M+Na] + : , found:

15 3-chloro-5-(4-methoxyphenyl)phenanthridin-6(5H)-one (2l). From 4'-chloro-N-(4-methoxyphenyl)-[1,1'- biphenyl]-2-carboxamide (33.8 mg, 0.1 mmol), compound 2l (Yield 67% mg.) was obtained. White solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.52 (dd, J = 8.0, 1.4 Hz, 1H), 8.24 (dd, J = 8.0, 1.0 Hz, 1H), 8.18 (d, J = 8.6 Hz, 1H), 7.79 (ddd, J = 8.4, 7.2, 1.4 Hz, 1H), 7.60 (ddd, J = 8.1, 7.2, 1.1 Hz, 1H), (m, 3H), 7.11 (d, J = 8.8 Hz, 2H), 6.73 (d, J = 2.0 Hz, 1H), 3.90 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 161.8, 159.8, 140.4, 135.0, 133.3, 133.0, 130.1, 129.9, 129.2, 128.4, 125.7, 124.3, 122.8, 121.7, 117.6, 116.8, 115.7, IR (cm -1 ) 3073, 2882, 2356, 2328, 1664, 1603, 1510, 1403, 1335, 1308, 1250, 1104, 1032, 811, 767, 529. HRMS (ESI + ) m/z calcd. C 20 H 14 ClNNaO + 2 [M+Na] + : , found: (4-methoxyphenyl)-3-methylphenanthridin-6(5H)-one (2m). From N-(4-methoxyphenyl)-4'-methyl-[1,1'- biphenyl]-2-carboxamide (31.7 mg, 0.1 mmol), compound 2m (Yield 52% mg.) was obtained. Pale yellow solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.51 (d, J = 7.9 Hz, 1H), 8.27 (d, J = 8.2 Hz, 1H), 8.16 (d, J = 8.2 Hz, 1H), 7.76 (t, J = 7.7 Hz, 1H), 7.55 (t, J = 7.6 Hz, 1H), 7.21 (d, J = 7.8 Hz, 2H), (m, 3H), 6.52 (s, 1H), 3.90 (s, 3H), 2.29 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 162.1, 159.5, 139.5, 134.1, 132.7, 130.9, 130.0, 129.0, 127.6, 125.5, 123.8, 122.9, 121.5, 117.2, 116.7, 115.4, 110.0, 55.5, IR (cm -1 ) 3068, 2887, 2359, 2328, 1660, 1610, 1510, 1317, 1249, 1132, 1033, 823, 769, 724, 692, 650, 545. HRMS (ESI + + ) m/z calcd. C 21 H 17 NNaO 2 [M+Na] + : , found:

16 2-methoxy-5-(4-methoxyphenyl)phenanthridin-6(5H)-one (2n). From 3'-methoxy-N-(4-methoxyphenyl)-[1,1'- biphenyl]-2-carboxamide (33.3 mg, 0.1 mmol), compound 2n (Yield 75% mg.) was obtained. White solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.54 (d, J = 7.9 Hz, 1H), 8.25 (d, J = 8.2 Hz, 1H), 7.78 (t, J = 7.7 Hz, 1H), 7.73 (d, J = 2.7 Hz, 1H), 7.59 (t, J = 7.5 Hz, 1H), 7.22 (d, J = 8.8 Hz, 2H), 7.09 (d, J = 8.8 Hz, 2H), 6.90 (dd, J = 9.1, 2.7 Hz, 1H), 6.67 (d, J = 9.2 Hz, 1H), 3.89 (s, 3H), 3.88 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 161.5, 159.5, 155.2, 133.9, 133.6, 132.6, 131.0, 130.0, 129.2, 128.2, 126.2, 121.8, 119.9, 118.3, 116.2, 115.4, 106.7, 55.8, IR (cm -1 ) 2947, 2882, 2359, 2328, 1653, 1509, 1424, 1345, 1299, 1248, 830, 778, 717, 613. HRMS (ESI + ) m/z calcd. C 21 H 17 NNaO + 3 [M+Na] + : , found: chloro-5-(4-methoxyphenyl)phenanthridin-6(5H)-one (2o). From 5-chloro-N-(4-methoxyphenyl)-[1,1'- biphenyl]-2-carboxamide (33.8 mg, 0.1 mmol), compound 2o (Yield 70% mg.) was obtained. White solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.46 (d, J = 8.6 Hz, 1H), 8.26 (d, J = 1.9 Hz, 1H), 8.18 (dd, J = 8.0, 1.5 Hz, 1H), 7.53 (dd, J = 8.4, 1.9 Hz, 1H), 7.32 (ddd, J = 8.5, 7.2, 1.5 Hz, 1H), 7.27 (t, J = 7.6 Hz, 1H), 7.21 (d, J = 8.9 Hz, 2H), 7.10 (d, J = 8.8 Hz, 2H), 6.74 (dd, J = 8.5, 1.3 Hz, 1H), 3.88 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 161.3, 159.7, 139.9, 139.5, 135.5, 130.9, 130.4, 129.9, 129.8, 128.4, 124.3, 123.1, 122.8, 121.7, 117.9, 117.2, 115.5, IR (cm -1 ) 3057, 2882, 2362, 2328, 1655, 1604, 1510, 1435, 1344, 1322, 1264, 1245, 1106, 1031, 826, 752, 729, 702, 680, 534. HRMS (ESI + ) m/z calcd. C 20 H 14 ClNNaO + 2 [M+Na] + : , found:

17 8-methoxy-5-(4-methoxyphenyl)phenanthridin-6(5H)-one (2p). From 4-methoxy-N-(4-methoxyphenyl)-[1,1'- biphenyl]-2-carboxamide (33.3 mg, 0.1 mmol), compound 2p (Yield 61% mg.) was obtained. White solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.26 (d, J = 9.0 Hz, 1H), (m, 1H), 7.98 (d, J = 2.4 Hz, 1H), 7.40 (d, J = 8.9 Hz, 1H), (m, 4H), 7.13 (d, J = 8.2 Hz, 2H), (m, 1H), 3.95 (s, 3H), 3.91 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 161.7, 159.6, 159.6, 138.5, 130.9, 130.0, 128.0, 127.5, 127.2, 123.6, 122.6, 122.5, 122.4, 119.2, 117.0, 115.4, 109.4, 55.6, IR (cm -1 ) 3063, 2887, 2367, 2328, 1653, 1608, 1510, 1354, 1317, 1268, 1248, 1035, 737, 574. HRMS (ESI + ) m/z calcd. C 21 H 17 NNaO + 3 [M+Na] + : , found: fluoro-5-(4-methoxyphenyl)phenanthridin-6(5H)-one (2q). From 4-fluoro-N-(4-methoxyphenyl)-[1,1'- biphenyl]-2-carboxamide (32.1 mg, 0.1 mmol), compound 2q (Yield 71% mg.) was obtained. Pale yellow solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.31 (dd, J = 9.0, 4.9 Hz, 1H), 8.20 (dd, J = 7.8, 1.7 Hz, 1H), 8.18 (dd, J = 9.1, 2.9 Hz, 1H), 7.50 (td, J = 8.4, 2.8 Hz, 1H), (m, 2H), 7.22 (d, J = 8.7 Hz, 2H), 7.11 (d, J = 8.7 Hz, 2H), 6.75 (dd, J = 8.0, 1.5 Hz, 1H), 3.89 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 163.2, 161.5, (d, J = 2.9 Hz), 159.7, 139.0, 130.5, (d, J = 2.8 Hz), 129.9, 128.9, (d, J = 7.9 Hz), (d, J = 7.8 Hz), (d, J = 2.9 Hz), (d, J = 23.2 Hz), 118.5, 117.2, 115.5, (d, J = 23.0 Hz), IR (cm -1 ) 3079, 2881, 2361, 2334, 1654, 1607, 1591, 1510, 1486, 1455, 1345, 1318, 1299, 1251, 1126, 935, 896, 822, 751, 648, 566, 538. HRMS (ESI + ) m/z calcd. C 20 H 14 FNNaO + 2 [M+Na] + : , found:

18 1-phenylquinolin-2(1H)-one (4a). From (E)-N-phenylcinnamamide (22.3 mg, 0.1 mmol), compound 4a (Yield 70% mg.) was obtained. White solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 7.77 (d, J = 9.6 Hz, 1H), (m, 3H), 7.51 (t, J = 7.5 Hz, 1H), 7.31 (t, J = 7.8 Hz, 1H), 7.27 (d, J = 7.4 Hz, 2H), 7.18 (t, J = 7.5 Hz, 1H), 6.77 (dd, J = 9.6, 1.4 Hz, 1H), 6.63 (d, J = 8.5 Hz, 1H). 13 C NMR (150 MHz, CDCl 3 ) δ 162.3, 141.2, 139.8, 137.7, 130.2, 130.2, 128.9, 128.8, 128.3, 122.3, 122.2, 120.3, IR (cm -1 ) 3057, 1663, 1593, 1567, 1498, 1452, 1405, 1331, 1298, 1264, 835, 737, 704, 575, 528. HRMS (ESI + ) m/z calcd. C 15 H 11 NNaO + [M+Na] + : , found: methoxy-1-phenylquinolin-2(1H)-one (4b). From (E)-3-(4-methoxyphenyl)-N-phenylacrylamide (25.3 mg, 0.1 mmol), compound 4b (Yield 50% mg.) was obtained. Yellow solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 7.71 (d, J = 9.4 Hz, 1H), 7.58 (t, J = 7.6 Hz, 2H), (m, 2H), 7.26 (d, J = 7.4 Hz, 2H), 6.78 (dd, J = 8.7, 2.2 Hz, 1H), 6.64 (d, J = 9.5 Hz, 1H), 6.07 (d, J = 2.1 Hz, 1H), 3.64 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 162.8, 161.4, 142.8, 139.7, 137.7, 130.2, 129.7, 129.0, 128.7, 118.9, 114.7, 110.1, 100.3, IR (cm -1 ) 3052, 1663, 1621, 1597, 1495, 1241, 1210, 1180, 1049, 1024, 841, 742, 704, 580, 526. HRMS (ESI + ) m/z calcd. C 16 H 13 NNaO + 2 [M+Na] + : , found:

19 7-methyl-1-phenylquinolin-2(1H)-one (4c). From (E)-N-phenyl-3-(p-tolyl)acrylamide (23.6 mg, 0.1 mmol), compound 4c (Yield 58% mg.) was obtained. White solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 7.72 (d, J = 9.4 Hz, 1H), 7.59 (t, J = 7.6 Hz, 2H), 7.51 (t, J = 7.5 Hz, 1H), 7.45 (d, J = 7.9 Hz, 1H), 7.26 (d, J = 8.4 Hz, 2H), 7.00 (d, J = 7.9 Hz, 1H), 6.69 (d, J = 9.5 Hz, 1H), 6.41 (s, 1H), 2.27 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 162.5, 141.3, 140.9, 139.6, 137.8, 130.2, 128.8, 128.8, 128.1, 123.7, 121.1, 118.2, 116.0, IR (cm -1 ) 3057, 1660, 1624, 1601, 1561, 1498, 1418, 1326, 1264, 1246, 1148, 1117, 901, 840, 808, 733, 698, 575. HRMS (ESI + ) m/z calcd. C 16 H 13 NNaO + [M+Na] + : , found: (tert-butyl)-1-phenylquinolin-2(1H)-one (4d). From (E)-3-(4-(tert-butyl)phenyl)-N-phenylacrylamide (27.8 mg, 0.1 mmol), compound 4d (Yield 60% mg.) was obtained. White solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 7.76 (d, J = 9.5 Hz, 1H), 7.61 (t, J = 7.8 Hz, 2H), 7.53 (dd, J = 9.9, 7.9 Hz, 2H), 7.30 (d, J = 7.3 Hz, 2H), (m, 1H), 6.74 (d, J = 9.5 Hz, 1H), 6.63 (d, J = 1.7 Hz, 1H), 1.17 (s, 9H). 13 C NMR (150 MHz, CDCl 3 ) δ 162.6, 154.0, 141.1, 139.4, 137.7, 130.1, 128.8, 128.8, 127.8, 121.4, 120.1, 118.1, 112.6, 35.1, IR (cm -1 ) 2962, 2871, 1669, 1624, 1604, 1498, 1416, 1259, 1161, 1123, 1032, 844, 758, 696, 575, 523. HRMS (ESI + ) m/z calcd. C 19 H 19 NNaO + [M+Na] + : , found: methyl-1-phenylquinolin-2(1H)-one (4e). From (E)-N,3-diphenylbut-2-enamide (23.8 mg, 0.1 mmol), compound 4e (Yield 60% mg.) was obtained. White solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 7.71 (dd, J = 7.9, 1.8 Hz, 1H), 7.57 (td, J = 7.8, 1.9 Hz, 2H), 7.50 (t, J = 7.4 Hz, 1H), 7.31 (ddd, J = 8.7, 7.1, 1.8 Hz, 1H), (m, 2H), 7.21 (t, J = 7.6 Hz, 1H), 6.66 (s, 1H), 6.65 (d, J = 8.7 Hz, 1H), 2.52 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 162.1, 147.3, 140.9, 137.7, 130.1, 130.0, 129.0, 128.8, 124.8, 122.1, 121.5, 121.1, 116.3, IR (cm -1 ) 3063, 1662, 1598, 1450, 1320, 1264, 873, 733, 709, 703, 671, 528. HRMS (ESI + ) m/z calcd. C 16 H 13 NNaO + [M+Na] + : , found:

20 4-ethyl-1-phenylquinolin-2(1H)-one (4f). From (E)-N,3-diphenylpent-2-enamide (25.0 mg, 0.1 mmol), compound 4f (Yield 53% mg.) was obtained. White solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 7.76 (d, J = 8.0 Hz, 1H), 7.57 (t, J = 7.5 Hz, 2H), 7.50 (t, J = 7.5 Hz, 1H), 7.30 (t, J = 7.9 Hz, 1H), 7.26 (d, J = 7.8 Hz, 2H), 7.19 (t, J = 7.6 Hz, 1H), 6.68 (s, 1H), 6.65 (d, J = 8.9 Hz, 1H), 2.92 (q, J = 7.6 Hz, 2H), 1.38 (t, J = 7.4 Hz, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 162.3, 152.4, 141.1, 137.8, 130.2, 129.8, 129.0, 128.8, 124.3, 122.1, 120.3, 119.5, 116.5, 25.1, IR (cm -1 ) 3063, 2975, 2931, 1660, 1596, 1564, 1498, 1448, 1394, 1347, 1320, 1264, 1076, 879, 733, 709, 671. HRMS (ESI + ) m/z calcd. C 17 H 15 NNaO + [M+Na] + : , found: methoxy-4-methyl-1-phenylquinolin-2(1H)-one (4g). From (E)-3-(4-methoxyphenyl)-N-phenylbut-2-enamide (26.7 mg, 0.1 mmol), compound 4g (Yield 61% mg.) was obtained. Yellow solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 7.63 (dd, J = 8.9, 1.8 Hz, 1H), 7.58 (t, J = 7.3 Hz, 2H), 7.50 (t, J = 7.2 Hz, 1H), 7.26 (d, J = 7.7 Hz, 2H), 6.80 (d, J = 8.7 Hz, 1H), 6.52 (s, 1H), 6.10 (s, 1H), 3.65 (s, 3H), 2.49 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 162.6, 161.0, 147.3, 142.6, 137.9, 130.2, 128.9, 128.8, 126.2, 118.7, 115.3, 109.5, 100.6, 55.3, IR (cm -1 ) 3063, 2969, 1657, 1600, 1557, 1390, 1323, 1264, 1230, 1081, 1030, 855, 733, 698. HRMS (ESI + ) m/z calcd. C 17 H 15 NNaO + 2 [M+Na] + : , found:

21 6,7,8-trimethoxy-4-methyl-1-phenylquinolin-2(1H)-one (4h). From (E)-N-phenyl-3-(3,4,5- trimethoxyphenyl)but-2-enamide (32.7 mg, 0.1 mmol), compound 4h (Yield 53% mg.) was obtained. Yellow oil. 1 H NMR (600 MHz, CDCl 3 ) δ 7.44 (t, J = 7.7 Hz, 2H), 7.35 (t, J = 7.4 Hz, 1H), 7.21 (d, J = 7.5 Hz, 2H), 6.89 (s, 1H), 6.57 (s, 1H), 3.92 (s, 3H), 3.81 (s, 3H), 3.12 (s, 3H), 2.45 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 162.9, 149.0, 146.7, 145.9, 142.3, 141.7, 129.6, 128.6, 127.6, 127.3, 120.9, 118.2, 102.0, 60.9, 60.8, 56.2, IR (cm -1 ) 3068, 2939, 1657, 1613, 1552, 1492, 1449, 1413, 1395, 1282, 1195, 1136, 1089, 1016, 865, 844, 764, 709, 607, 557. HRMS (ESI + ) m/z calcd. C 17 H 15 NNaO + 2 [M+Na] + : , found: phenyl-4-(3-phenylpropyl)quinolin-2(1H)-one (4i). From (E)-N,3,6-triphenylhex-2-enamide (34.2 mg, 0.1 mmol), compound 4i (Yield 53% mg.) was obtained. White solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 7.66 (d, J = 8.1 Hz, 1H), 7.60 (t, J = 7.3 Hz, 2H), 7.52 (t, J = 7.1 Hz, 1H), (m, 8H), 7.18 (td, J = 7.7, 2.1 Hz, 1H), 6.70 (s, 1H), 6.67 (dd, J = 8.5, 2.3 Hz, 1H), 2.90 (t, J = 7.2 Hz, 2H), 2.82 (t, J = 7.1 Hz, 2H), (m, 2H). 13 C NMR (150 MHz, CDCl 3 ) δ 162.1, 150.9, 141.4, 141.2, 137.8, 130.1, 129.9, 128.9, 128.8, 128.5, 128.4, 126.1, 124.4, 122.1, 120.5, 120.2, 116.5, 35.5, 31.5, IR (cm -1 ) 3057, 1662, 1597, 1498, 1452, 1320, 1264, 898, 732, 706. HRMS (ESI + ) m/z calcd. C 24 H 21 NNaO + [M+Na] + : , found: cyclopropyl-1-phenylquinolin-2(1H)-one (4j). From (E)-3-cyclopropyl-N,3-diphenylacrylamide (26.5 mg, 0.1 mmol), compound 4j (Yield 60% mg.) was obtained. White solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.12 (dd, J = 8.1, 1.4 Hz, 1H), 7.60 (t, J = 7.6 Hz, 2H), 7.52 (t, J = 7.5 Hz, 1H), 7.34 (ddd, J = 8.5, 7.1, 1.4 Hz, 1H), (m, 3H), 6.66 (dd, J = 8.6, 1.2 Hz, 1H), 6.53 (s, 1H), (m, 1H), (m, 2H), (m, 2H). 13 C NMR (150 MHz, CDCl 3 ) δ 162.5, 152.2, 140.9, 137.8, 130.1, 129.9, 128.9, 128.8, 125.0, 122.1, 121.4, 117.8, 116.3, 12.6, 7.0. IR (cm -1 ) 3068, 2920, 1660, 1597, 1496, 1449, 1408, 1320, 1010, 879, 753, 709, 696, 619, 545. HRMS (ESI + ) m/z calcd. C 18 H 15 NNaO + [M+Na] + : , found:

22 1,4-diphenylquinolin-2(1H)-one (4k). From N,3,3-triphenylacrylamide (29.9 mg, 0.1 mmol), compound 4k (Yield 79% mg.) was obtained. Pale yellow solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 7.61 (td, J = 7.9, 2.0 Hz, 2H), 7.57 (d, J = 8.1 Hz, 1H), (m, 6H), (m, 3H), 7.12 (t, J = 7.6 Hz, 1H), 6.75 (s, 1H), 6.72 (d, J = 8.4 Hz, 1H). 13 C NMR (150 MHz, CDCl 3 ) δ 161.9, 151.8, 141.4, 137.7, 137.1, 130.2, 130.2, 128.9, 128.9, 128.9, 128.8, 128.6, 127.3, 122.1, 121.6, 120.2, IR (cm -1 ) 3057, 1662, 1600, 1492, 1447, 1380, 1323, 1301, 1264, 1076, 1057, 882, 752, 739, 702, 676, 545. HRMS (ESI + ) m/z calcd. C 21 H 15 NNaO + [M+Na] + : , found: phenyl-4-(pyridin-4-yl)quinolin-2(1H)-one (4l). From (E)-N,3-diphenyl-3-(pyridin-4-yl)acrylamide and (Z)- N,3-diphenyl-3-(pyridin-4-yl)acrylamide mixtures (30.0 mg, 0.1 mmol), compound 4l (Yield 56% mg.) was obtained. Pale yellow solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 8.79 (d, J = 5.9 Hz, 2H), 7.62 (t, J = 7.7 Hz, 2H), 7.54 (t, J = 7.5 Hz, 1H), 7.44 (dd, J = 8.1, 1.4 Hz, 1H), 7.42 (d, J = 5.9 Hz, 2H), 7.36 (ddd, J = 8.6, 7.1, 1.4 Hz, 1H), 7.32 (dd, J = 8.3, 1.3 Hz, 2H), 7.15 (t, J = 7.6 Hz, 1H), (m, 2H). 13 C NMR (150 MHz, CDCl 3 ) δ 161.4, 150.2, 149.0, 145.0, 141.5, 137.4, 130.7, 130.3, 129.1, 128.8, 126.6, 123.6, 122.5, 122.0, 119.0, IR (cm -1 ) 3057, 1665, 1600, 1591, 1495, 1452, 1383, 1320, 1265, 882, 838, 758, 734, 709, 550. HRMS (ESI + ) m/z calcd. C 20 H 14 N 2 NaO + [M+Na] + : , found:

23 7-methoxy-4-(4-methoxyphenyl)-1-phenylquinolin-2(1H)-one (4m). From 3,3-bis(4-methoxyphenyl)-Nphenylacrylamide (35.9 mg, 0.1 mmol), compound 4m (Yield 77% mg.) was obtained. Yellow solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 7.59 (t, J = 7.8 Hz, 2H), (m, 2H), 7.41 (d, J = 8.1 Hz, 2H), 7.31 (d, J = 7.1 Hz, 2H), 7.02 (d, J = 8.1 Hz, 2H), 6.70 (d, J = 8.9 Hz, 1H), 6.57 (s, 1H), 6.14 (s, 1H), 3.88 (s, 3H), 3.64 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 162.5, 161.1, 160.0, 151.4, 143.2, 137.9, 130.2, 130.1, 129.7, 128.9, 128.8, 128.8, 118.5, 114.5, 114.0, 109.5, 100.6, 55.4, IR (cm -1 ) 3057, 2964, 1655, 1610, 1547, 1508, 1455, 1422, 1380, 1321, 1291, 1263, 1231, 1177, 1125, 1028, 835, 733, 699, 538. HRMS (ESI + + ) m/z calcd. C 23 H 19 NNaO 3 [M+Na] + : , found: (4-iodophenyl)quinolin-2(1H)-one (4n). From (E)-N-(4-iodophenyl)cinnamamide (34.9 mg, 0.1 mmol), compound 4n (Yield 72% mg.) was obtained. White solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 7.91 (d, J = 8.4 Hz, 2H), 7.77 (d, J = 9.5 Hz, 1H), 7.57 (dd, J = 7.7, 1.5 Hz, 1H), 7.33 (ddd, J = 8.6, 7.2, 1.5 Hz, 1H), 7.19 (td, J = 7.5, 1.0 Hz, 1H), 7.03 (d, J = 8.5 Hz, 2H), 6.75 (d, J = 9.6 Hz, 1H), 6.65 (d, J = 8.5 Hz, 1H). 13 C NMR (150 MHz, CDCl 3 ) δ 162.1, 140.8, 140.0, 139.5, 137.4, 130.9, 130.3, 128.4, 122.5, 122.1, 120.3, 115.7, IR (cm -1 ) 3046, 1663, 1597, 1545, 1449, 1145, 1010, 841, 758, 742, 583, 528, 515. HRMS (ESI + ) m/z calcd. C 15 H 10 INNaO + [M+Na] + : , found: (4-(tert-butyl)phenyl)quinolin-2(1H)-one (4o). From (E)-N-(4-(tert-butyl)phenyl)cinnamamide (27.9 mg, 0.1 mmol), compound 4o (Yield 63% mg.) was obtained. Yellow solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 7.76 (d, J = 9.5 Hz, 1H), (m, 3H), 7.31 (ddd, J = 8.6, 7.2, 1.5 Hz, 1H), (m, 3H), 6.76 (d, J = 9.6 Hz, 1H), 6.66 (d, J = 8.5 Hz, 1H), 1.38 (s, 9H). 13 C NMR (150 MHz, CDCl 3 ) δ 162.4, 151.7, 141.4, 139.7, 134.8, 130.1, 128.2, 128.1, 127.2, 122.3, 122.2, 120.3, 116.1, 34.8, IR (cm -1 ) 3052, 2964, 1664, 1593, 1564, 1450, 1405, 1298, 1246, 1142, 832, 753, 605, 523. HRMS (ESI + ) m/z calcd. C 19 H 19 NNaO + [M+Na] + : , found:

24 1-(p-tolyl)quinolin-2(1H)-one (4p). From (E)-N-(p-tolyl)cinnamamide (23.7 mg, 0.1 mmol), compound 4p (Yield 65% mg.) was obtained. White solid. mp o C. 1 H NMR (600 MHz, CDCl 3 ) δ 7.76 (dd, J = 9.6, 1.5 Hz, 1H), 7.56 (dd, J = 7.8, 1.7 Hz, 1H), 7.38 (d, J = 7.7 Hz, 2H), 7.31 (dd, J = 8.7, 7.0 Hz, 1H), (m, 3H), 6.77 (dd, J = 9.5, 1.5 Hz, 1H), 6.67 (d, J = 8.5 Hz, 1H), 2.44 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 162.4, 141.3, 139.7, 138.8, 134.9, 130.9, 130.1, 128.5, 128.2, 122.3, 122.2, 120.3, 116.0, IR (cm -1 ) 3057, 2926, 1662, 1591, 1564, 1515, 1449, 1264, 1249, 835, 735, 704, 610, 526. HRMS (ESI + ) m/z calcd. C 16 H 13 NNaO + [M+Na] + : , found: (o-tolyl)quinolin-2(1H)-one (4q). From (E)-N-(o-tolyl)cinnamamide (23.7 mg, 0.1 mmol), compound 4q (Yield 55% mg.) was obtained. Colorless oil. 1 H NMR (600 MHz, CDCl 3 ) δ 7.79 (d, J = 9.5 Hz, 1H), 7.59 (d, J = 7.6 Hz, 1H), (m, 3H), 7.31 (t, J = 7.8 Hz, 1H), (m, 2H), 6.78 (d, J = 9.5 Hz, 1H), 6.53 (d, J = 8.4 Hz, 1H), 2.00 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 161.8, 140.5, 139.8, 136.6, 136.3, 131.6, 130.4, 129.2, 128.7, 128.4, 127.8, 122.3, 122.3, 120.4, 115.4, IR (cm -1 ) 3057, 2926, 1658, 1593, 1564, 1495, 1449, 1298, 1249, 1131, 832, 757, 742, 586, 531. HRMS (ESI + ) m/z calcd. C 16 H 13 NNaO + [M+Na] + : , found: (m-tolyl)quinolin-2(1H)-one (4r). From (E)-N-(m-tolyl)cinnamamide (23.7 mg, 0.1 mmol), compound 4r (Yield 54% mg.) was obtained. Colorless oil. 1 H NMR (600 MHz, CDCl 3 ) 7.76 (d, J = 9.6 Hz, 1H), 7.56 (d, J

25 = 7.7 Hz, 1H), 7.46 (t, J = 7.6 Hz, 1H), (m, 2H), 7.17 (t, J = 7.5 Hz, 1H), (m, 2H), 6.76 (d, J = 9.5 Hz, 1H), 6.65 (d, J = 8.5 Hz, 1H), 2.41 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ 162.3, 141.2, 140.3, 139.7, 137.5, 130.1, 130.0, 129.7, 129.2, 128.2, 125.7, 122.2, 122.2, 120.3, 116.0, IR (cm -1 ) 3057, 2926, 1659, 1594, 1562, 1491, 1449, 1295, 1245, 1139, 830, 782, 753, 735, 699, 630, 525. HRMS (ESI + ) m/z calcd. C 16 H 13 NNaO + [M+Na] + : , found:

26 Appendix Ⅰ Spectral Copies of 1 H and 13 C NMR Data Obtained in this Study

27 5-pheny lphenanthridin-6(5h)-one (2a)

28 5-(4-methoxyphenyl)phenanthridin-6(5H)-one (2b)

29 5-(p-tolyl)phenanthridin-6(5H)-one (2c)

30 5-(4-(tert-butyl)phenyl)phenanthridin-6(5H)-one (2d)

31 5-(m-tolyl)phenanthridin-6(5H)-one (2e)

32 5-(o-tolyl)phenanthridin-6(5H)-one (2f)

33 5-(4-bromophenyl)phenanthridin-6(5H)-one (2g)

34 5-(4-iodophenyl)phenanthridin-6(5H)-one (2h)

35 3-methoxy-5-(4-methoxyphenyl)phenanthridin-6(5H)-one (2i)

36 5-(4-methoxyphenyl)-3-(trifluoromethyl)phenanthridin-6(5H)-one (2j)

37 3-(tert-butyl)-5-(4-methoxyphenyl)phenanthridin-6(5H)-one (2k)

38 3-chloro-5-(4-methoxyphenyl)phenanthridin-6(5H)-one (2l)

39 5-(4-methoxyphenyl)-3-methylphenanthridin-6(5H)-one (2m)

40 2-methoxy-5-(4-methoxyphenyl)phenanthridin-6(5H)-one (2n)

41 9-chloro-5-(4-methoxyphenyl)phenanthridin-6(5H)-one (2o)

42 8-methoxy-5-(4-methoxyphenyl)phenanthridin-6(5H)-one (2p)

43 8-fluoro-5-(4-methoxyphenyl)phenanthridin-6(5H)-one (2q)

44 1-phenylquinolin-2(1H)-one (4a)

45 7-methoxy-1-phenylquinolin-2(1H)-one (4b)

46 7-methyl-1-phenylquinolin-2(1H)-one (4c)

47 7-(tert-butyl)-1-phenylquinolin-2(1H)-one (4d)

48 4-methyl-1-phenylquinolin-2(1H)-one (4e)

49 4-ethyl-1-phenylquinolin-2(1H)-one (4f)

50 7-methoxy-4-methyl-1-phenylquinolin-2(1H)-one (4g)

51 6,7,8-trimethoxy-4-methyl-1-phenylquinolin-2(1H)-one (4h)

52 1-phenyl-4-(3-phenylpropyl)quinolin-2(1H)-one (4i)

53 4-cyclopropyl-1-phenylquinolin-2(1H)-one (4j)

54 1,4-diphenylquinolin-2(1H)-one (4k)

55 1- phenyl-4-(pyridin-4-yl)quinolin-2(1h)-one (4l)

56 7-methoxy-4-(4-methoxyphenyl)-1-phenylquinolin-2(1H)-one (4m)

57 1-(4-iodophenyl)quinolin-2(1H)-one (4n)

58 1-(4-(tert-butyl)phenyl)quinolin-2(1H)-one (4o)

59 1-(p-tolyl)quinolin-2(1H)-one (4p)

60 1-(o-tolyl)quinolin-2(1H)-one (4q)

61 1-(m-tolyl)quinolin-2(1H)-one (4r)