233
Table I. Physical data of the intermediates.
a
Compound M.p. (°C)
Formula
1H-NMR (ppm) [Solvent]
[recryst. solv.]
11
12
111–113
95–98
C10H8ClNO5 [CH2Cl2-Hexane]
3.94 (3H, s), 6.78 (1H, d, J = 14.2), 6.80 (1H, d, J = 14.2), 7.55 (1H, dd,
J = 8.6, J = 2.3), 7.89 (1H, d, J = 2.3), 8.21 (1H, d, J = 8.6) [CDCl3]
3.31 (6H, s), 3.52 (2H, s), 3.63 (3H, s), 7.20–7.60 (2H, m), 7.78 (1H, d,
J = 1.7) [CDCl3]
C12H14ClNO6 [CH2Cl2-Hexane]
13
14
125–127
116–117
C11H12ClNO4 [MeOH-Et2O]
C11H14ClNO2 [CH2Cl2-Hexane]
3.16 (2H, s), 3.36 (6H, s), 7.00–7.40 (3H, m), 8.70 (1H, br) [CDCl3]
2.91 (2H, s), 3.30 (8H, s), 3.90 (1H, br), 6.50–6.70 (2H, m), 6.86 (1H, d,
J = 7.9) [CDCl3]
15
17
135–137
99–102
C17H14ClNO2 [CH2Cl2-Hexane]
C17H14ClNO2 [CH2Cl2-Hexane]
2.30 (3H, s), 3.66 (2H, s), 4.39 (2H, s), 7.10–7.30 (7H, m) [CDCl3]
2.09 (3H, s), 4.40 (2H, s), 4.85 (2H, s), 6.86–7.68 (6H, m), 7.76–8.00 (1H,
m) [DMSO-d6]
20
21
24
120–122
165–168
134–135
C17H14ClNOS [CH2Cl2-Hexane]
C17H15ClN2O2 [CH2Cl2-Hexane]
C21H24ClNO6S [EtOH]
2.54 (3H, s), 3.20 (2H, t, J = 6.3), 4.13 (2H, t, J = 6.3), 6.92–7.40 (6H, m),
8.40 (1H, d, J = 9.2) [CDCl3]
2.26 (3H, s), 3.04 (2H, t, J = 6.4), 4.14 (2H, t, J = 6.4), 6.80–7.36 (6H, m),
7.68 (1H, br), 8.31 (1H, d, J = 9.2) [CDCl3]
1.23 (3H, t, J = 7.2), 1.80–2.10 (2H, m), 2.42 (2H, t, J = 7.2), 2.43 (3H,
s), 3.40–3.80 (2H, m), 3.82 (3H, s), 4.10 (2H, q, J = 7.2), 7.20–7.60 (6H,
m), 7.83 (1H, d, J = 8.6) [CDCl3]
26
27
28
30
31
33
37
38
39
40
83–84
99–103
138–139
121–123
189–194
174–177
97–98
C17H16ClNO3S [CH2Cl2-Hexane]
C10H10ClNO [Et2O-hexane]
C18H16ClNO2 [EtOH]
1.80–2.20 (2H, m), 2.43 (2H, t, J = 5.8), 2.44 (3H, s), 3.83 (2H, t, J = 6.4),
7.20–7.40 (3H, m), 7.50–7.80 (4H, m) [CDCl3]
1.90–2.40 (2H, m), 2.80 (2H, t, J = 6.3), 3.00–3.40 (2H, m), 4.69 (1H, br),
6.50–6.90 (2H, m), 7.63 (1H, d, J = 8.6) [CDCl3]
1.90–2.30 (2H, m), 2.41 (3H, s), 2.90 (2H, t, J = 6.3), 3.80–4.20 (2H, m),
6.70–7.10 (6H, m), 7.84 (1H, d, J = 8.0) [CDCl3]
2.55 (3H, s), 2.64 (3H, s), 7.00–8.00 (6H, m), 9.06 (1H, s), 12.19 (1H, s)
[CDCl3]
2.22 (3H, s), 2.44 (3H, s), 7.12–7.76 (6H, m), 8.54 (1H, d, J = 2.2), 11.32
(1H, s), 11.54 (1H, s) [DMSO-d6]
2.38 (3H, s), 2.91 (2H, t, J = 6.5), 4.40 (2H, t, J = 6.5), 6.72–7.44 (5H, m),
8.12 (1H, d, J = 8.4) [CDCl3]
2.34 (3H, s), 2.71 (2H, t, J = 6.6), 4.15 (2H, t, J = 6.6), 7.76 (1H, d,
J = 5.5), 8.00 (1H, d, J = 5.5) [DMSO-d6]
2.33 (3H, s), 2.72 (2H, t, J = 6.6), 4.15 (2H, t, J = 6.6), 7.80 (1H, s)
[DMSO-d6]
2.43 (2H, t, J = 7.1), 3.65 (2H, t, J = 7.1), 7.44 (1H, br), 7.00 (1H, s)
[DMSO-d6]
2.30 (3H, s), 2.73 (2H, t, J = 6.5), 3.96 (2H, t, J = 6.5), 7.04–7.52 (5H, m)
[DMSO-d6]
C16H14ClNO2 [CH2Cl2-Hexane]
C16H15ClN2O2 [CH2Cl2-Hexane]
C16H13ClN2O2 [CH2Cl2-Hexane]
C9H9NO2S [CH2Cl2-Hexane]
C9H8ClNO2S [CH2Cl2-Hexane]
C7H6ClNOS [CH2Cl2-Hexane]
C15H12ClNO2S [CH2Cl2-Hexane]
65–68
128–129
118–121
aCompounds were analysed by HR-MS.
Table II. Physical date of compounds 3–9.
Compound
M.p. (°C)a (dec)
Formulab
1H-NMR (DMSO-d6, ppm)
3
4
5
138–140
193–195
172–173
C17H14ClKN2O5S 2.25 (3H, s), 3.71 (2H, s), 4.51 (2H, s), 7.20–7.80 (7H, m)
C17H14ClKN2O5S 2.09 (3H, s), 4.40 (2H, s), 4.85 (2H, s), 6.86–7.68 (6H, m), 7.76–8.00 (1H, m)
C17H14ClKN2O5S 2.44 (3H, s), 3.08 (2H, t, J = 6.4), 4.02 (2H, t, J = 6.4), 6.72–7.52 (6H, m), 8.11 (1H,
d, J = 8.6)
6
114–115
C18H16ClKN2O5S 1.50–2.00 (2H, m), 2.26 (3H, s), 2.40–2.80 (2H, m), 3.50–4.00 (2H, m), 6.80–7.50
(7H, m)
7
8
9
171–174
130–133
172–175
C16H14ClKN2O5S 2.23 (3H, s), 2.45 (3H, s), 7.04–7.72 (6H, m), 8.48 (1H, d, J = 1.8), 10.93 (1H, s)
C16H13ClKN3O5S 2.27 (3H, s), 2.88–4.16 (4H, m), 6.80–7.36 (5H, m), 8.19 (1H, d, J = 7.9)
C15H12ClKN2O5S2 2.26 (3H, s), 2.64–2.92 (2H, m), 3.48–3.92 (2H, m), 7.20–7.44 (5H, m)
aRecrystalisation solvent CH2Cl2-MeOH. bCompounds 3 and 5 were analysed for C, H and N. Analytical results obtained for these elements
were within ± 0.4% of the calculated values for the formulae shown. Compounds 4 and 6–9 were analysed by HR-FAB-MS.