E
B. Wang et al.
Paper
Synthesis
1H NMR (400 MHz, CDCl3): = 8.43 (d, J = 8.7 Hz, 2 H), 8.19 (d, J = 8.7
Hz, 1 H), 7.96 (d, J = 8.0 Hz, 1 H), 7.65 (d, J = 1.9 Hz, 2 H), 7.57–7.47 (m,
2 H).
1H NMR (400 MHz, CDCl3): = 8.55 (dt, J = 8.1, 1.8 Hz, 2 H), 8.24 (d, J =
2.0 Hz, 1 H), 7.94 (d, J = 8.6 Hz, 1 H), 7.69 (t, J = 7.4 Hz, 1 H), 7.57 (t, J =
7.7 Hz, 2 H), 7.53 (dd, J = 8.6, 2.4 Hz, 1 H).
13C NMR (100 MHz, CDCl3): = 183.94, 166.72, 153.75, 137.00,
13C NMR (100 MHz, CDCl3): = 184.89, 168.89, 154.57, 135.18,
133.57, 132.73, 131.77, 129.46, 127.75, 126.99, 125.72, 122.14.
134.61, 134.11, 132.98, 131.27, 128.54, 128.20, 125.21, 122.93.
HRMS (ESI): m/z [M + H]+ calcd for C14H9BrNOS: 317.9583; found:
HRMS (ESI): m/z [M + H]+ calcd for C14H9ClNOS: 274.0088; found:
317.9577.
274.0083.
Benzo[d]thiazol-2-yl(3-bromophenyl)methanone (3h)
(5-Chlorobenzo[d]thiazol-2-yl)(p-tolyl)methanone (3m)
Yellow solid; yield: 102 mg, 0.32 mmol (80%); mp 98–100 °C.
White solid; yield: 102 mg, 0.356 mmol (89%); mp 115–117 °C.
1H NMR (400 MHz, CDCl3): = 8.70 (t, J = 1.8 Hz, 1 H), 8.54 (dt, J = 7.8,
1.3 Hz, 1 H), 8.30–8.24 (m, 1 H), 8.05–8.00 (m, 1 H), 7.82–7.77 (m, 1
H), 7.64–7.54 (m, 2 H), 7.45 (t, J = 7.9 Hz, 1 H).
1H NMR (400 MHz, CDCl3): = 8.47 (d, J = 8.3 Hz, 2 H), 8.24 (d, J = 2.5
Hz, 1 H), 7.94 (d, J = 9.1 Hz, 1 H), 7.52 (dd, J = 8.6, 2.0 Hz, 1 H), 7.37 (d,
J = 8.0 Hz, 2 H), 2.48 (s, 3 H).
13C NMR (100 MHz, CDCl3): = 183.87, 166.35, 153.77, 137.04,
136.65, 136.62, 133.97, 130.01, 129.87, 127.86, 127.06, 125.86,
122.62, 122.17.
13C NMR (100 MHz, CDCl3): = 184.36, 169.25, 154.57, 145.27,
135.14, 132.88, 132.05, 131.40, 129.29, 128.04, 125.14, 122.89, 21.86.
HRMS (ESI): m/z [M + H]+ calcd for C15H11ClNOS: 288.0244; found:
288.0240.
HRMS (ESI): m/z [M + H]+ calcd for C14H9BrNOS: 317.9583; found:
317.9577.
(4-Bromophenyl)(5-chlorobenzo[d]thiazol-2-yl)methanone (3n)15a
Benzo[d]thiazol-2-yl(3-chlorophenyl)methanone (3i)11
Yellow solid; yield: 113 mg, 0.32 mmol (80%); mp 184–186 °C.
Yellow solid; yield: 85 mg, 0.312 mmol (78%); mp 98–100 °C.
1H NMR (400 MHz, CDCl3): = 8.44 (d, J = 8.6 Hz, 2 H), 8.21 (s, 1 H),
7.92 (d, J = 8.6 Hz, 1 H), 7.69 (d, J = 8.6 Hz, 2 H), 7.51 (dd, J = 8.6, 2.0 Hz,
1 H).
13C NMR (100 MHz, CDCl3): = 183.75, 168.52, 154.50, 135.21,
133.31, 133.13, 132.73, 131.89, 129.77, 128.38, 125.23, 122.95.
1H NMR (400 MHz, CDCl3): = 8.56 (t, J = 2.1 Hz, 1 H), 8.50–8.46 (m, 1
H), 8.29–8.24 (m, 1 H), 8.05–8.01 (m, 1 H), 7.67–7.62 (m, 1 H), 7.62–
7.54 (m, 2 H), 7.52 (t, J = 8.1 Hz, 1 H).
13C NMR (100 MHz, CDCl3): = 184.00, 166.40, 153.78, 137.04,
136.41, 134.66, 133.76, 131.12, 129.78, 129.40, 127.86, 127.06,
125.85, 122.17.
HRMS (ESI): m/z [M + H]+ calcd for C14H8BrClNOS: 351.9193; found:
351.9189.
HRMS (ESI): m/z [M + H]+ calcd for C14H9ClNOS: 274.0088; found:
274.0083.
(5-Methoxybenzo[d]thiazol-2-yl)(naphthalen-2-yl)methanone
(3o)9
(3-Bromophenyl)(5-chlorobenzo[d]thiazol-2-yl)methanone (3j)
Yellow solid; yield: 119 mg, 0.372 mmol (93%); mp 179–182 °C.
Yellow solid; yield: 114 mg, 0.324 mmol (81%); mp 107–108 °C.
1H NMR (400 MHz, CDCl3): = 9.30 (s, 1 H), 8.41 (d, J = 10.3 Hz, 1 H),
8.14 (d, J = 9.1 Hz, 1 H), 8.06 (d, J = 8.1 Hz, 1 H), 7.95 (d, J = 8.7 Hz, 1 H),
7.89 (d, J = 8.1 Hz, 1 H), 7.66–7.59 (m, 1 H), 7.59–7.53 (m, 1 H), 7.41
(d, J = 2.5 Hz, 1 H), 7.19 (d, J = 11.6 Hz, 1 H), 3.92 (s, 3 H).
1H NMR (400 MHz, CDCl3): = 8.68 (t, J = 1.7 Hz, 1 H), 8.51 (d, J = 7.9
Hz, 1 H), 8.25 (d, J = 2.0 Hz, 1 H), 7.93 (d, J = 8.6 Hz, 1 H), 7.79 (dd, J =
8.0, 2.0 Hz, 1 H), 7.52 (dd, J = 8.6, 2.0 Hz, 1 H), 7.43 (t, J = 7.9 Hz, 1 H).
13C NMR (100 MHz, CDCl3): = 183.46, 168.14, 154.49, 136.87,
136.29, 135.23, 134.00, 133.19, 130.06, 129.86, 128.48, 125.35,
122.94, 122.68.
13C NMR (100 MHz, CDCl3): = 184.85, 164.87, 159.73, 148.56,
139.08, 135.84, 134.04, 132.45, 132.39, 130.16, 128.85, 128.22,
127.73, 126.64, 126.46, 125.84, 117.59, 103.38, 55.84.
HRMS (ESI): m/z [M + H]+ calcd for C14H8BrClNOS: 351.9193; found:
HRMS (ESI): m/z [M + H]+ calcd for C19H14NO2S: 329.0740; found:
351.9189.
329.0735.
(5-Chlorobenzo[d]thiazol-2-yl)(m-tolyl)methanone (3k)
(5-Methoxybenzo[d]thiazol-2-yl)(4-methoxyphenyl)methanone
(3p)
Yellow solid; yield: 100 mg, 0.348 mmol (87%); mp 114–116 °C.
Yellow solid; yield: 109 mg, 0.364 mmol (91%); mp 147–149 °C.
1H NMR (400 MHz, CDCl3): = 8.35 (d, J = 7.5 Hz, 1 H), 8.26 (s, 1 H),
8.22 (d, J = 2.0 Hz, 1 H), 7.91 (d, J = 8.6 Hz, 1 H), 7.52–7.45 (m, 2 H),
7.43 (t, J = 7.5 Hz, 1 H), 2.46 (s, 3 H).
13C NMR (100 MHz, CDCl3): = 185.10, 169.01, 154.55, 138.36,
135.17, 134.95, 134.62, 132.93, 131.46, 128.64, 128.41, 128.12,
125.20, 122.91, 21.44.
1H NMR (400 MHz, CDCl3): = 8.61 (d, J = 9.0 Hz, 2 H), 8.06 (d, J = 9.1
Hz, 1 H), 7.37 (s, 1 H), 7.14 (d, J = 11.6 Hz, 1 H), 7.00 (d, J = 9.0 Hz, 2 H),
3.88 (s, 6 H).
13C NMR (100 MHz, CDCl3): = 183.13, 165.35, 164.17, 159.52,
148.48, 138.86, 133.66, 127.89, 126.20, 117.37, 113.77, 103.36, 55.79,
55.50.
HRMS (ESI): m/z [M + H]+ calcd for C15H11ClNOS: 288.0244; found:
288.0240.
HRMS (ESI): m/z [M + H]+ calcd for C16H14NO3S: 300.0689; found:
300.0685.
(5-Chlorobenzo[d]thiazol-2-yl)(phenyl)methanone (3l)
White solid; yield: 93 mg, 0.34 mmol (85%); mp 134–136 °C.
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