6
Tetrahedron
ACCEPTED MANUSCRIPT
4.3.1 3-Phenylquinolin-4(1H)-one (2a). White solid (216.6
4.3.8 3-(2-Tolyl)quinolin-4(1H)-one (2h). Yellowish-brown
mg, 98% yield), mp 259-260 °C (lit. 258-261 °C)1l; H NMR
(400 MHz, DMSO-d6) δ 11.98 (d, J = 4.8 Hz, 1H), 8.15 (d, J =
7.9 Hz, 1H), 8.08 (d, J = 6.2 Hz, 1H), 7.67 (s, 1H), 7.65 (s, 1H),
7.62-7.56 (m, 1H), 7.53 (d, J = 8.1 Hz, 1H), 7.30 (m, 3H), 7.21 (t,
J = 7.3 Hz, 1H).; 13C NMR (100 MHz, DMSO-d6) δ174.75,
139.25, 138.11, 136.11, 131.55, 128.39 (2C), 127.82(2C),
126.34, 125.81, 125.57, 123.26, 119.76, 118.18; HRMS (ESI)
calculated for C15H12NO [M+H]+ 222.0913, found 222.0902.
solid (222.7 mg, 95% yield), mp 250-251 °C (lit. 243-245 °C)1k;
1H NMR (400 MHz, DMSO-d6) δ 11.97 (s, 1H), 8.18 (d, J = 7.9
Hz, 1H), 7.91 (s, 1H), 7.73-7.53 (m, 2H), 7.35 (t, J = 7.3 Hz, 1H),
7.30-7.08 (m, 4H), 2.17 (s, 3H); 13C NMR (100MHz, DMSO-d6)
δ 174.47, 139.63, 138.48, 137.52, 136.48, 131.46, 130.62,
129.38, 127.03, 125.44, 125.37, 125.29, 123.10, 121.76, 118.19,
19.85; HRMS (ESI) calculated for C16H14NO [M+H]+ 236.1070,
found 236.1037.
1
4.3.2 3-(2-Fluorophenyl)quinolin-4(1H)-one (2b). White solid
(217.6 mg, 91% yield), mp > 270°C (lit. 257-261 °C)1k; 1H NMR
(400 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.19 (d, J = 8.0 Hz, 1H),
8.08 (s, 1H), 7.68 (t, J = 7.5 Hz, 1H), 7.61 (d, J = 8.2 Hz, 1H),
7.52 (t, J = 7.4 Hz, 1H), 7.37 (t, J = 6.9 Hz, 2H), 7.23 (t, J = 8.3
Hz, 2H); 13C NMR (100 MHz, DMSO-d6) δ 174.28, 159.95 (d, J
(C, F)= 245.4 Hz, 1C), 139.50, 139.17 (d, J (C, F)= 2.0 Hz, 1C),
132.29 (d, J (C, F)= 3.0 Hz, 1C), 131.73, 128.81 (d, J (C, F)= 8.1 Hz,
1C), 125.43, 125.40, 123.88 (d, J (C, F)= 15.2 Hz, 1C), 123.84(d, J
(C, F)= 4.0 Hz, 1C ), 123.41, 118.28, 115.35, 115.13; HRMS (ESI)
calculated for C15H11FNO [M+H]+ 240.0819, found 240.0840.
4.3.9 3-(4-Methoxyphenyl)quinolin-4(1H)-one (2i). Light
brown solid (236.5 mg, 94% yield), mp > 270 °C (lit. 292 °C)5;
1H NMR (400 MHz, DMSO-d6) δ 11.98 (s, 1H), 8.21 (d, J = 8.0
Hz, 1H), 8.10 (s, 1H), 7.76-7.52 (m, 4H), 7.34 (t, J = 7.4 Hz, 1H),
6.97 (s, 1H), 6.95 (s, 1H), 3.78 (s, 3H); 13C NMR (100 MHz,
DMSO-d6)
δ
174.78, 157.94, 139.19, 137.40, 131.38,
129.46(2C), 128.40, 125.67, 125.54, 123.07, 119.52, 118.11,
113.28(2C), 55.04; HRMS (ESI) calculated for C16H14NO2
[M+H]+ 252.1019, found 252.1006.
4.3.10 3-(Thiophen-3-yl)quinolin-4(1H)-one (2j).Yellowish-
1
brown solid (215.2 mg, 95% yield), mp > 270 °C; H NMR (400
4.3.3 3-(3-Fluorophenyl)quinolin-4(1H)-one (2c). White solid
(220.5 mg, 92% yield), mp 261-262 °C; H NMR (400 MHz,
MHz, DMSO-d6) δ 12.00 (s, 1H), 8.35 (d, J = 4.1 Hz, 1H), 8.21
(d, J = 2.5 Hz, 1H), 8.13 (d, J = 8.0 Hz, 1H), 7.63-7.46 (m, 3H),
7.42 (dd, J = 4.8, 3.1 Hz, 1H), 7.24 (t, J = 7.3 Hz, 1H); 13C NMR
(100 MHz, DMSO-d6) δ 174.43, 138.74, 137.49, 136.00, 131.40,
126.54, 125.61, 125.52, 124.62, 123.31, 121.38, 118.22, 115.11;
HRMS (ESI) calculated for C13H10NOS [M+H]+ 228.0478, found
228.0454.
1
DMSO-d6) δ 12.17 (s, 1H), 8.28 (s, 1H), 8.23 (d, J = 8.0 Hz, 1H),
7.77-7.64 (m, 2H), 7.62 (s, 1H), 7.60 (s, 1H), 7.43 (q, J = 7.6 Hz,
1H), 7.37 (t, J = 7.5 Hz, 1H), 7.10 (td, J = 8.5, 2.7 Hz, 1H); 13C
NMR (100 MHz, DMSO-d6) δ 174.53, 161.92 (d, J (C, F) = 241.4
Hz, 1C), 139.17, 138.65, 138.56 (d, J (C, F) = 9.1 Hz, 1C), 131.70,
129.56 (d, J (C, F) = 8.1 Hz, 1C), 125.87, 125.57, 123.96 (d, J (C, F)
= 3.0 Hz,1C), 123.48, 118.25, 117.96 (d, J (C, F) = 2.0 Hz, 1C),
114.81 (d, J (C, F) = 22.2 Hz, 1C), 112.89 (d, J (C, F) = 21.2 Hz, 1C);
HRMS (ESI) calculated for C15H11FNO [M+H]+ 240.0819, found
240.0830.
4.3.4 3-(4-Fluorophenyl)quinolin-4(1H)-one (2d). White solid
(219.8 mg, 92% yield), mp > 270 °C (lit. 244-246 °C)1l; 1H NMR
(400 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.26-8.20 (m, 1H), 8.18
(s, 1H), 7.84-7.73 (m, 2H), 7.67 (td, J = 7.6, 6.9, 1.3 Hz, 1H),
7.60 (d, J = 8.1 Hz, 1H), 7.42-7.31 (m, 1H), 7.22 (t, J = 8.9 Hz,
2H); 13C NMR (100 MHz, DMSO-d6) δ 174.63, 160.93 (d, J (C, F)
= 244.4 Hz, 1C), 139.26, 138.07, 132.41 (d, J (C, F) = 2.0 Hz, 1C)
131.58, 130.21(d, J (C, F) = 8.1 Hz, 2C), 125.74, 125.53, 123.30,
118.68, 118.19, 114.53 (d, J (C, F) = 21.2 Hz, 2C); HRMS (ESI)
calculated for C15H11FNO [M+H]+ 240.0819, found 240.0821.
4.3.11 3-(3-Bromo-4-methoxyphenyl)quinolin-4(1H)-one (2k).
1
Yellowish-brown solid (299.8 mg, 91% yield), mp > 270 °C; H
NMR (400 MHz, DMSO-d6) δ 12.09 (d, J = 6.2 Hz, 1H), 8.22 (s,
1H), 8.20 (s, 1H), 8.06 (d, J = 2.1 Hz, 1H), 7.73 (dd, J = 8.5, 2.1
Hz, 1H), 7.67 (t, J = 7.6 Hz, 1H), 7.60 (d, J = 8.2 Hz, 1H), 7.36
(t, J = 7.4 Hz, 1H), 7.15 (d, J = 8.5 Hz, 1H), 3.88 (s, 3H).;13C
NMR (100 MHz, DMSO-d6) δ 174.59, 153.90, 139.17, 137.90,
132.45, 131.52, 129.97, 128.53, 125.69, 125.50, 123.28, 118.20,
117.80, 112.07, 109.95, 56.18; HRMS (ESI) calculated for
C16H13BrNO2 [M+H]+ 330.0124, found 330.0109.
4.3.12 3-(3,4-Bis(benzyloxy)phenyl)quinolin-4(1H)-one (2l).
Yellowish-brown solid (390.2 mg, 90% yield), mp 182-185 °C;
1H NMR (400 MHz, DMSO-d6) δ 12.01 (d, J = 5.9 Hz, 1H), 8.22
(d, J = 8.0 Hz, 1H), 8.11 (d, J = 6.1 Hz, 1H), 7.65 (t, J = 7.6 Hz,
1H), 7.62-7.54 (m, 2H), 7.49 (m, 4H), 7.43-7.26 (m, 8H), 7.08 (d,
J = 8.4 Hz, 1H), 5.17 (s, 4H); 13C NMR (100 MHz, DMSO-d6) δ
174.72, 147.73, 147.03, 139.12, 137.67, 137.45, 131.42, 129.40,
128.34(3C), 128.33(2C), 127.70, 127.67, 127.57(2C),
127.42(2C), 125.73, 125.56, 123.15, 121.20, 119.30, 118.12,
115.18, 114.24, 70.32, 70.12; HRMS (ESI) calculated for
C29H24NO3 [M+H]+ 434.1751, found 434.1734.
4.3.13 6-Chloro-3-phenylquinolin-4(1H)-one (2m). Yellowish-
brown solid (232.7 mg, 91% yield), mp > 270 °C (lit. > 300 °C)1l;
1H NMR (400 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.21 (s, 1H),
8.15 (d, J = 2.4 Hz, 1H), 7.69 (m, 4H), 7.40 (t, J = 7.6 Hz, 2H),
7.29 (t, J = 7.3 Hz, 1H); 13C NMR (100 MHz, DMSO-d6) δ
173.52, 138.53, 137.89, 135.70, 131.67, 128.37 (2C), 127.93,
127.85 (2C), 126.79, 126.55, 124.45, 120.71, 119.99; HRMS
(ESI) calculated for C15H11ClNO [M+H]+ 256.0524, found
256.0507.
4.3.5 3-(4-Bromophenyl)quinolin-4(1H)-one (2e). Light brown
1
solid (278.9 mg, 93% yield), mp > 270 °C; H NMR (400 MHz,
DMSO-d6) δ 12.14 (s, 1H), 8.24 (d, J = 9.4 Hz, 2H), 7.76 (s, 1H),
7.74 (s, 1H), 7.68 (t, J = 7.1 Hz, 1H), 7.60 (m, 3H), 7.37 (t, J =
7.3 Hz, 1H); 13C NMR (100 MHz, DMSO-d6) δ 174.51, 139.22,
138.28, 135.37, 131.64, 130.67(2C), 130.32(2C), 125.80, 125.55,
123.42, 119.33, 118.25(2C); HRMS (ESI) calculated for
C15H11BrNO [M+H]+ 300.0019, found 300.0005.
4.3.6 3-(4-Chlorophenyl)quinolin-4(1H)-one (2f). Light brown
solid (240.5 mg, 94% yield), mp 253-255 °C (lit. 250-252 °C)1k;
1H NMR (400 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.23 (d, J = 6.8
Hz, 2H), 7.82 (s, 1H), 7.80 (s, 1H), 7.73-7.64 (m, 1H), 7.61 (d, J
= 8.1 Hz, 1H), 7.45 (s, 1H), 7.43 (s, 1H), 7.37 (t, J = 7.4 Hz, 1H);
13C NMR (100 MHz, DMSO-d6) δ 174.55, 139.23, 138.30,
134.99, 131.64, 130.81, 129.96(2C), 127.75(2C), 125.80, 125.55,
123.40, 118.23(2C); HRMS (ESI) calculated for C15H11ClNO
[M+H]+ 256.0524, found 256.0525.
4.3.14 7-Chloro-3-phenylquinolin-4(1H)-one (2n). Yellowish-
1
brown solid (240.1 mg, 94% yield), mp > 270 °C; H NMR (400
4.3.7 3-(4-Tolyl)quinolin-4(1H)-one (2g). Yellowish-brown
MHz, DMSO-d6) δ 11.99 (s, 1H), 8.20 (d, J = 8.7 Hz, 1H), 8.17
(s, 1H), 7.75-7.67 (m, 2H), 7.64 (d, J = 2.0 Hz, 1H), 7.42-7.33
(m, 3H), 7.32 – 7.26 (m, 1H); 13C NMR (100 MHz, DMSO-d6) δ
174.19, 140.02, 138.62, 136.11, 135.66, 128.38(2C), 127.96,
127.84(2C), 126.56, 124.40, 123.59, 120.39, 117.29; HRMS
(ESI) calculated for C15H11ClNO [M+H]+ 256.0524, found
256.0533
1
solid (221.5 mg, 94% yield), mp > 270 °C (lit. 287-289 °C)1l; H
NMR (400 MHz, DMSO-d6) δ 11.97 (s, 1H), 8.11 (s, 1H), 8.01
(s, 1H), 7.77-7.72 (m, 1H), 7.71 (s, 1H), 7.50 (s, 2H), 7.39 (t, J =
7.6 Hz, 2H), 7.27 (t, J = 7.3 Hz, 1H), 2.43 (s, 3H).; 13C NMR
(100 MHz, DMSO-d6) δ 174.48, 137.74, 137.34, 136.31, 132.95,
132.52, 128.36(2C), 127.79(2C), 126.22, 125.78, 124.75, 119.40,
118.11, 20.79; HRMS (ESI) calculated for C16H14NO [M+H]+
236.1070, found 236.1047.
4.3.15 6-Methyl-3-phenylquinolin-4(1H)-one (2o). Yellowish-
brown solid (214.2 mg, 91% yield), mp > 270 °C (lit. >300 °C)1l;