10.1002/chem.201805000
Chemistry - A European Journal
COMMUNICATION
Compound 4e
66.2, 47.7, 47.0. HRMS (ESI) calcd for C25H23BrN2O2S [M+Na]+
517.0556; found 517.0521.
Pale yellow liquid. 1H NMR (500 MHz, CDCl3): δ 7.74 (dd, J = 8.0, 1.5 Hz,
1H), 7.59 (d, J = 8.0 Hz, 1H), 7.48 (d, J = 3.0 Hz, 1H), 7.32 (t, J = 8.0 Hz,
1H), 7.29-7.26 (m, 1H), 7.19-7.15 (m, 2H), 5.04 (s, 1H), 3.74-3.65 (m,
4H), 2.66-2.64 (m, 4H). 13C NMR (126 MHz, CDCl3): δ 137.2, 133.3,
130.7, 130.1, 129.4, 128.9, 127.0, 125.4, 125.3, 121.8, 84.3, 83.6, 67.2,
61.4, 49.8. HRMS (ESI) calcd for C17H16BrNOS [M+H]+ 362.0209; found
362.0191.
Compound 10c
Diastereomer 1: Off white solid, mp 100-102 °C. 1H NMR (500 MHz,
CDCl3): δ 7.81 (d, J = 8.5 Hz, 2H), 7.65 (d, J = 8.5 Hz, 2H), 7.35 (d, J =
8.0 Hz, 2H), 7.29-7.27 (m, 4H), 7.12 (d, J = 8.0 Hz, 2H), 5.78 (s, 1H),
3.19-3.16 (m, 2H), 2.99-2.96 (m, 2H), 2.41 (s, 3H), 2.35 (s, 3H), 1.71-
1.70 (m, 2H), 1.64-1.61 (m, 2H), 1.40-1.37 (m, 2H).13C NMR (126 MHz,
CDCl3): δ 142.9, 141.0, 139.9, 138.3, 132.7, 131.6, 129.4, 129.1, 128.9,
128.3, 128.3, 128.0, 120.4, 90.0, 83.8, 48.3, 46.3, 25.7, 23.8, 21.6, 21.5.
HRMS (ESI) calcd for C28H29ClN2OS [M+Na]+ 499.1581; found 499.1560.
Compound 4f
Pale yellow liquid. 1H NMR (500 MHz, CDCl3): δ 7.39 (d, J = 8.0 Hz, 2H),
7.13 (d, J = 8.0 Hz, 2H), 7.00 (d, J = 3.0 Hz, 1H), 6.60 – 6.59 (m, 1H),
4.90 (s, 1H), 3.76-3.73 (m, 4H), 2.73 – 2.68 (m, 2H), 2.65 – 2.61 (m, 2H),
2.46 (s, 3H), 2.36 (s, 3H). 13C NMR (126 MHz, CDCl3): δ 140.2, 140.0,
138.4, 131.7, 129.0, 126.2, 124.2, 119.6, 87.5, 83.6, 67.1, 57.9, 49.6,
21.5, 15.4. HRMS (ESI) calcd for C19H21NOS [M+H]+ 312.1417; found
312.1405.
Diastereomer 2: Off white solid, mp 98-100 °C. 1H NMR (500 MHz,
CDCl3): δ 7.77 (d, J = 8.5 Hz, 2H), 7.63 (d, J = 8.5 Hz, 2H), 7.34 (d, J =
8.5 Hz, 2H), 7.28-7.27 (m, 4H), 7.04 (d, J = 8.5 Hz, 2H), 5.58 (s, 1H),
2.89 (brs, 2H), 2.77-2.75 (m, 2H), 2.40 (s, 3H), 2.30 (s, 3H), 1.49-1.47 (m,
4H), 1.33-1.31 (m, 2H). 13C NMR (126 MHz, CDCl3): δ 142.9, 141.7,
137.9, 132.9, 132.9, 131.7, 129.4, 128.8, 128.7, 128.6, 128.3, 120.4,
90.4, 83.7, 47.7, 47.6, 25.4, 23.7, 21.6, 21.5. HRMS (ESI) calcd for
C28H29ClN2OS [M+Na]+ 499.1581; found 499.1556.
Compound 4h
Pale yellow liquid. 1H NMR (500 MHz, CDCl3): δ 7.33 (d, J = 8.0 Hz, 2H),
7.10 (d, J = 8.0 Hz, 2H), 3.79 – 3.72 (m, 4H), 3.39 (t, J = 7.5 Hz, 1H),
2.76 – 2.72 (m, 2H), 2.59 – 2.55 (m, 2H), 2.34 (s, 3H), 1.73 (q, J = 7.5 Hz,
2H), 1.07 (t, J = 7.5 Hz, 3H). 13C NMR (126 MHz, CDCl3): δ 138.0, 131.6,
128.9, 120.1, 86.3, 86.2, 67.1, 59.8, 49.7, 26.1, 21.4, 11.2. HRMS (ESI)
calcd for C16H21NO [M+H]+ 244.1696; found 244.1670.
Compound 10d
Diastereomer 1: Yellowish sticky liquid. 1H NMR (500 MHz, CDCl3): δ
7.94 (d, J = 8.0, 2H), 7.61 (t, J = 7.0 Hz, 1H), 7.55-7.52 (m, 3H), 7.42-
7.40 (m, 1H), 7.33 (d, J = 8.0 Hz, 2H), 7.14-7.08 (m, 3H), 5.79 (s, 1H),
3.77-3.71 (m, 4H), 3.21 (brs, 2H), 3.00 (brs, 2H), 2.36 (s, 3H).13C NMR
(126 MHz, CDCl3): δ 150.1 (dd, J = 248.2, 12.6 Hz), 149.5 (dd, J = 246.9,
12.6 Hz), 139.0, 138.6, 134.2, 132.7, 131.4, 129.2, 128.9, 127.8, 123.1
(m), 119.6, 116.7 (d, J = 17.6 Hz), 116.4 (d, J = 17.6 Hz), 89.0, 84.2, 66.4,
47.4, 45.7, 21.4. HRMS (ESI) calcd for C26H24F2N2O2S [M+Na]+
489.1419; found 489.1389.
Compound 10a
Diastereomer 1: Yellowish sticky liquid. 1H NMR (500 MHz, CDCl3): δ
7.94 (d, J = 8.5 Hz, 2H), 7.59-7.56 (m, 3H), 7.51 (t, J = 8.0 Hz, 2H), 7.33
(d, J = 8.0 Hz, 2H), 7.15-7.11 (m, 4H), 5.81 (s, 1H), 3.78-3.68 (m, 4H),
3.22 (br, 2H), 3.00 (br, 2H), 2.35 (s, 3H), 2.32 (s, 3H). 13C NMR (126
MHz, CDCl3): δ 138.9, 138.3, 136.8, 134.7, 132.5, 131.6, 129.2, 129.1,
128.8, 128.0, 127.2, 120.3, 90.1, 83.7, 66.6, 47.6, 46.5, 21.5, 21.2.
HRMS (ESI) calcd for C27H28N2O2S [M+Na]+ 467.1764; found 467.1738.
Diastereomer 2: Yellowish sticky liquid. 1H NMR (500 MHz, CDCl3) δ
7.90 (d, J = 7.5 Hz, 2H), 7.59-7.52 (m, 4H), 7.37 (br, 1H), 7.28 (d, J = 8.0
Hz, 2H), 7.16-7.14 (m, 1H), 7.06 (d, J = 8.0 Hz, 2H), 5.60 (s, 1H), 3.61-
3.57 (m, 4H), 2.93-2.92 (m, 2H), 2.81-2.79 (m, 2H), 2.31 (s, 3H). 13C
NMR (126 MHz, CDCl3): δ 150.4 (dd, J = 245.7, 15.1 Hz), 149.8 (dd, J =
245.7, 15.1 Hz), 139.9, 138.3, 134.8, 132.8, 131.7, 129.0, 128.9, 128.3,
123.1 (m), 120.0, 117.1 (d, J = 17.6 Hz), 116.3 (d, J = 17.6 Hz), 89.4,
84.3, 66.3, 47.5, 46.9, 21.5. HRMS (ESI) calcd for C26H24F2N2O2S
[M+Na]+ 489.1419; found 489.1380.
Diastereomer 2: Yellowish sticky liquid. 1H NMR (500 MHz, CDCl3): δ
7.90-7.88 (m, 2H), 7.56-7.54 (m, 3H), 7.50 (d, J = 8.0 Hz, 2H), 7.28 (d, J
= 8.0 Hz, 2H), 7.18 (d, J = 8.0 Hz, 2H), 7.03 (d, J = 8.5 Hz, 2H), 5.65 (s,
1H), 3.54-3.50 (m, 4H), 2.86 (br, 2H), 2.74-2.69 (m, 2H), 2.35 (s, 3H),
2.29 (s, 3H). 13C NMR (126 MHz, CDCl3): δ 140.0, 137.9, 137.1, 135.0,
132.6, 131.8, 129.3, 128.8, 128.8, 128.3, 127.3, 120.6, 90.7, 83.4, 66.3,
48.0, 47.0, 21.5, 21.3. HRMS (ESI) calcd for C27H28N2O2S [M+Na]+
467.1764; found 467.1743.
Compound 10e
Diastereomer 1: Off white solid, mp 85-87 °C. 1H NMR (500 MHz,
CDCl3): δ 7.88 (d, J = 8.5 Hz, 2H), 7.58 (d, J = 8.0 Hz, 2H), 7.36 (d, J =
8.0 Hz, 2H), 7.27-7.26 (m, 2H), 7.13-7.10 (m, 4H), 5.80 (s, 1H), 3.42-3.40
(m, 2H), 3.25-3.23 (m, 2H), 2.40 (s, 3H), 2.34 (s, 3H), 2.31 (s, 3H), 1.72-
1.68 (m, 4H). 13C NMR (126 MHz, CDCl3): δ 142.8, 137.4, 136.6, 131.6,
129.4, 129.1, 129.0, 128.4, 128.1, 127.3, 127.3, 120.8, 90.1, 81.8, 48.9,
47.0, 25.3, 21.5, 21.2, 21.2. HRMS (ESI) calcd for C28H30N2OS [M+Na]+
465.1971; found 465.1941.
Compound 10b
Diastereomer 1: Light yellowish solid, mp 95-98 °C 1H NMR (500 MHz,
CDCl3): δ 7.94-7.93 (m, 2H), 7.59-7.57 (m, 3H), 7.53 (t, J = 7.5 Hz, 2H),
7.46-7.43 (m, 4H), 7.33-7.32 (m, 3H), 5.80 (s, 1H), 3.77-3.71 (m, 4H),
3.21 (s, 2H), 3.00 (s, 2H). 13C (126 MHz, CDCl3): δ 141.0, 134.4, 132.7,
131.7, 131.4, 129.1, 129.0, 128.5, 128.5, 128.0, 123.0, 121.3, 90.2, 84.1,
66.5, 47.5, 46.3. HRMS (ESI) calcd for C25H23BrN2O2S [M+Na]+
517.0556; found 517.0528.
Diastereomer 2: Off white solid, mp 90-92 °C. 1H NMR (500 MHz,
CDCl3): δ 7.88 (d, J = 8.5 Hz, 2H), 7.58 (d, J = 8.0 Hz, 2H), 7.27-7.26 (m,
4H), 7.17 (d, J = 7.0 Hz, 2H), 7.03 (d, J = 8.0 Hz, 2H), 5.63 (s, 1H), 3.13-
3.11 (m, 2H), 3.01-2.99 (m, 2H), 2.40 (s, 3H), 2.35 (s, 3H), 2.29 (s, 3H),
1.63-1.60 (m, 4H). 13C NMR (126 MHz, CDCl3): δ 142.6, 140.0, 137.5,
136.6, 133.9, 131.6, 129.3, 128.9, 128.6, 128.2, 127.0, 120.7, 90.9 83.1,
48.3, 47.8, 25.1, 21.4, 21.4, 21.1. HRMS (ESI) calcd for C28H30N2OS
[M+Na]+ 465.1971; found 465.1947.
Diastereomer 2: Light yellowish solid, mp 97-99 °C. 1H NMR (500 MHz,
CDCl3): δ 7.90 (d, J = 8.0 Hz, 2H), 7.58-7.50 (m, 7H), 7.40-7.39 (m, 2H),
7.26-7.25 (m, 3H), 5.63 (s, 1H), 3.58-3.54 (m, 4H), 2.92-2.89 (m, 2H),
2.76-2.73 (m, 2H). 13C NMR (126 MHz, CDCl3): δ 141.8, 132.8, 131.9,
131.7, 129.1, 129.0, 128.3, 128.2, 128.1, 123.3, 123.2, 121.4, 90.6, 83.9,
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