ACCEPTED MANUSCRIPT
3H), 1.70 (s, 2H), 1.59 (s, 1H). 13C NMR (101 MHz, CDCl3)
1H), 7.55 (d, J = 8.2 Hz, 1H), 7.45 (ddd, J = 5.6, 3.6, 1.2 Hz, 2H),
7.23 (t, J = 7.5 Hz, 1H), 2.27 (s, 3H), 2.25 (s, 3H), 2.16 (s, 3H),
2.01 (d, J = 14.2 Hz, 6H), 1.85 (s, 3H). 13C NMR (101 MHz,
CDCl3) δ=169.99, 169.89, 140.15, 138.70, 137.03, 136.82, 136.60,
136.33, 132.03, 131.71, 130.64, 127.66, 127.52, 126.22, 124.09,
123.64, 123.44, 123.41, 123.08, 120.61, 119.61, 118.69, 110.96,
110.77, 14.61, 14.33, 13.53, 13.21, 13.17. MS (APCI): m/z
calculated for [M]+: 510.1; found 510.5. Anal. Calc. for
C30H26N2O2S2: C, 70.56; H, 5.13; N, 5.49; Found: C, 70.52; H,
5.18; N, 5.58.
δ=169.09, 143.14, 137.63, 137.13, 136.81, 136.73, 136.54, 136.33,
135.94, 135.61, 135.58, 131.93, 131.77, 131.56, 131.50, 130.64,
130.58, 130.33, 130.26, 130.20, 130.10, 128.40, 128.20, 128.08,
127.94, 127.56, 127.53, 127.41, 126.55, 126.50, 122.97, 121.51,
120.43, 120.18, 120.10, 116.16, 115.57, 115.48, 110.16, 21.38,
14.59, 14.41, 14.33, 14.02, 13.50, 13.46, 13.18, 13.00. MS (APCI):
m/z calculated for [M]+: 600.2; found 600.6. Anal. Calc. for
C37H32N2O2S2: C, 73.97; H, 5.37; N, 4.66; Found: C, 73.97; H,
5.37; N, 4.66.
15: yield: 65%. m.p. 216.2-216.9 °C . 1H NMR (400 MHz,
CDCl3) δ=8.26 (d, J = 7.7 Hz, 1H), 8.17 (d, J = 7.7 Hz, 1H),
7.51–7.35 (m, 7H), 7.34–7.27 (m, 2H), 7.08 (t, J = 6.4 Hz, 1H),
2.30–2.19 (m, 6H), 2.03 (s, 1H), 1.95 (s, 2H), 1.88 (d, J = 14.4 Hz,
3H), 1.79 (d, J = 10.6 Hz, 3H), 1.72 (s, 2H), 1.61 (s, 1H). 13C NMR
(101 MHz, CDCl3) δ=169.16, 169.12, 169.07, 142.92, 138.16,
137.51, 137.00, 136.76, 136.73, 136.63, 136.56, 136.50, 136.38,
136.09, 131.92, 131.86, 131.55, 131.52, 130.62, 130.55, 130.27,
130.23, 129.52, 129.47, 129.41, 129.34, 128.81, 128.54, 128.42,
128.20, 127.52, 127.47, 127.44, 127.34, 126.57, 123.01, 121.52,
120.54, 120.23, 115.48, 110.05, 14.78, 14.60, 14.38, 14.33, 13.81,
13.52, 13.32, 13.19, 13.17, 13.14. MS (APCI): m/z calculated for
[M]+: 586.2; found 586.5. Anal. Calc. for C36H30N2O2S2: C, 73.69;
H, 5.15; N, 4.77; Found: C, 73.54; H, 5.25; N, 4.80.
19: yield: 80%. m.p. 251.5.0-252.0 °C . 1H NMR (400 MHz,
CDCl3) δ=8.15 (s, 1H), 8.08 (d, J = 7.7 Hz, 1H), 7.55 - 7.45 (m,
3H), 7.42 (d, J = 8.1 Hz, 1H), 7.23 (d, J = 7.3 Hz, 1H), 4.32 (t, J =
7.2 Hz, 2H), 2.29 (s, 3H), 2.27 (s, 3H), 2.15 (s, 3H), 2.00 (s, 6H),
1.87 (dd, J = 13.7, 6.2 Hz, 2H), 1.83 (s, 3H), 1.42 - 1.20 (m, 12H),
0.87 (t, J = 6.8 Hz, 3H). 13C NMR (101 MHz, CDCl3) δ=169.88,
169.79, 141.02, 139.54, 136.99, 136.77, 136.56, 136.29, 132.07,
131.76, 130.55, 127.72, 127.58, 126.09, 123.94, 123.15, 123.10,
123.06, 123.03, 122.65, 120.72, 119.08, 118.78, 118.76, 109.00,
108.93, 43.27, 31.83, 29.41, 29.19, 29.01, 27.33, 22.64, 14.61,
14.34, 14.11, 13.52, 13.21, 13.19. MS (APCI): m/z calculated for
[M]+: 622.3; found 622.7. Anal. Calc. for C38H42N2O2S2: C, 73.27;
H, 6.80; N, 4.50; Found: C, 73.52; H, 6.68; N, 4.51.
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20: yield: 80%. m.p. 80.2-81.1 °C . H NMR (400 MHz, CDCl3)
16: yield: 67%. m.p. 262.3-263.5 °C . 1H NMR (400 MHz,
CDCl3) δ=8.24 (d, J = 7.7 Hz, 1H), 8.15 (d, J = 7.6 Hz, 1H), 7.38 (t,
J = 7.4 Hz, 4H), 7.31 (t, J = 7.4 Hz, 1H), 7.24 (s, 1H), 7.17–7.04
(m, 2H), 7.01 (dd, J = 8.1, 3.8 Hz, 1H), 2.24 (t, J = 9.1 Hz, 6H),
2.02 (s, 1H), 1.97 (s, 2H), 1.87 (d, J = 11.7 Hz, 3H), 1.81 (d, J =
7.6 Hz, 3H), 1.70 (s, 2H), 1.63 (s, 1H). 13C NMR (101 MHz, CDCl3)
δ=169.27, 169.17, 169.14, 163.07, 160.62, 160.60, 160.58, 142.96,
137.63, 137.60, 137.10, 136.82, 136.70, 136.66, 136.64, 136.48,
136.35, 134.11, 134.08, 131.85, 131.76, 131.43, 131.40, 130.82,
130.78, 130.73, 130.50, 130.46, 130.41, 130.35, 130.27, 130.09,
130.01, 127.53, 127.50, 127.44, 127.36, 127.27, 127.23, 126.69,
126.53, 122.99, 121.61, 120.70, 120.38, 120.32, 116.68, 116.63,
116.55, 116.46, 116.40, 116.33, 116.24, 115.47, 115.37, 109.85,
14.62, 14.49, 14.34, 13.59, 13.53, 13.20, 13.16, 13.05. MS (APCI):
m/z calculated for [M+1]+: 604.2; found 605.4. Anal. Calc. for
C36H29N2O2FS2: C, 71.50; H, 4.83; N, 4.63; Found: C, 71.40; H,
5.01; N, 4.56.
δ=8.19 (s, 1H), 8.12 (d, J = 7.8 Hz, 1H), 7.57 - 7.49 (m, 3H), 7.46
(d, J = 8.2 Hz, 1H), 7.26 (d, J = 7.4 Hz, 1H), 4.43 (q, J = 7.2 Hz,
2H), 2.32 (s, 3H), 2.30 (s, 3H), 2.18 (s, 3H), 2.03 (s, 6H), 1.86 (s,
3H), 1.47 (t, J = 7.2 Hz, 3H). 13C NMR (101 MHz, CDCl3)
δ=169.87, 169.78, 140.48, 139.08, 136.99, 136.77, 136.56, 136.28,
132.07, 131.75, 130.55, 127.71, 127.58, 126.12, 124.00, 123.99,
123.26, 123.10, 123.07, 122.77, 120.80, 119.13, 118.89, 118.87,
108.77, 108.70, 37.70, 14.61, 14.34, 13.85, 13.53, 13.21, 13.19.
MS (APCI): m/z calculated for [M-1]-: 538.2; found 537.6. Anal.
Calc. for C32H30N2O2S2: C, 71.34; H, 5.61; N, 5.20; Found: C,
71.23; H, 5.82; N, 5.29.
21: yield: 72%. m.p. 232.2-232.7 °C . 1H NMR (400 MHz,
CDCl3) δ=8.19 (d, J = 1.3 Hz, 1H), 8.11 (d, J = 7.7 Hz, 1H), 7.53 -
7.43 (m, 3H), 7.39 (d, J = 8.1 Hz, 1H), 7.31 - 7.22 (m, 4H), 7.15 (d,
J = 6.6 Hz, 2H), 5.54 (s, 2H), 2.29 (s, 3H), 2.27 (s, 3H), 2.14 (s,
3H), 1.99 (d, J = 2.3 Hz, 6H), 1.83 (s, 3H). 13C NMR (101 MHz,
CDCl3) δ=169.84, 169.75, 141.23, 139.75, 136.99, 136.87, 136.77,
136.60, 136.32, 132.07, 131.75, 130.58, 128.86, 127.69, 127.61,
127.55, 126.45, 126.39, 124.19, 123.56, 123.54, 123.38, 122.85,
120.78, 119.60, 118.80, 109.28, 109.17, 46.71, 14.62, 14.35, 13.53,
13.22, 13.20. MS (APCI): m/z calculated for [M]+: 600.2; found
600.6. Anal. Calc. for C37H32N2O2S2: C, 73.97; H, 5.37; N, 4.66;
Found: C, 73.85; H, 5.46; N, 4.60.
17: yield: 46%. m.p. 256.0.0-256.8 °C . 1H NMR (400 MHz,
CDCl3) δ=8.27 (d, J = 8.3 Hz, 1H), 7.74 (d, J = 7.0 Hz, 1H), 7.68
(d, J = 7.6 Hz, 1H), 7.52–7.41 (m, 3H), 7.36–7.28 (m, 1H), 7.15 (d,
J = 8.2 Hz, 2H), 6.83 (d, J = 8.0 Hz, 2H), 2.32–2.24 (m, 6H),
2.21–2.11 (m, 6H), 2.07 (s, 1H), 1.99 (d, J = 7.2 Hz, 3H), 1.88 (s,
2H). 13C NMR (101 MHz, CDCl3) δ=169.05, 169.02, 168.99,
168.95, 144.50, 140.96, 138.12, 138.03, 137.93, 137.90, 137.36,
136.98, 135.93, 135.80, 135.78, 135.75, 135.73, 133.06, 132.88,
132.52, 132.33, 132.31, 131.89, 131.61, 130.18, 130.15, 129.36,
128.87, 128.65, 128.17, 128.02, 127.78, 127.72, 127.03, 126.08,
125.52, 122.79, 120.21, 119.73, 119.26, 21.44, 14.53, 14.38, 14.35,
14.16, 13.34, 13.25, 13.20, 13.13, 13.04. MS (APCI): m/z
calculated for [M+1]+: 664.2; found 665.3. Anal. Calc. for
C37H32N2O4S3: C, 66.84; H, 4.85; N, 4.21; Found: C, 67.11; H, 4.82;
N, 4.07.
22: yield: 74%. m.p. 155.1-156.1 °C . 1H NMR (400 MHz,
CDCl3) δ=8.17 (d, J = 2.0 Hz, 1H), 8.09 (d, J = 7.6 Hz, 1H), 7.32
(dd, J = 5.8, 3.2 Hz, 8H), 7.26 - 7.21 (m, 5H), 7.19 (s, 1H), 7.11 (d,
J = 8.8 Hz, 2H), 2.29 (s, 3H), 2.26 (s, 3H), 2.13 (s, 3H), 1.97 (d, J =
5.1 Hz, 6H), 1.81 (s, 3H). 13C NMR (101 MHz, CDCl3) δ=169.80,
169.71, 141.28, 139.72, 138.63, 136.96, 136.75, 136.59, 136.31,
132.05, 131.74, 130.57, 128.75, 128.40, 128.01, 127.66, 127.52,
126.09, 123.91, 123.74, 123.51, 123.49, 123.27, 120.52, 119.56,
118.38, 111.12, 110.80, 62.52, 14.60, 14.33, 13.50, 13.19. MS
(APCI): m/z calculated for [M-1]-: 676.2; found 675.9. Anal. Calc.
for C43H36N2O2S2: C, 76.30; H, 5.36; N, 4.14; Found: C, 76.02; H,
18: yield: 92%. m.p. 225.0-226.0 °C . 1H NMR (400 MHz,
CD3CN) δ=9.54 (s, 1H), 8.18 - 8.06 (m, 2H), 7.62 (d, J = 8.6 Hz,
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