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organic layer was dried with Na2SO4. After removal of the solvent
under reduced pressure, the residue was purified by flash column
chromatography on neutral silica gel (AcOEt/hexane = 9:1) to afford
4-(4′-methylphenyl)-2-phenylthiazole 3b in 95 % yield (477.5 mg).
752 cm–1. H NMR (400 MHz, CDCl3): δ = 3.97 (s, 3 H), 7.02 (dd, J =
8.3, 0.9 Hz, 1 H), 7.10 (td, J = 7.6, 0.9 Hz, 1 H), 7.32 (td, J = 7.7,
1.8 Hz, 1 H), 7.39–7.48 (m, 3 H), 7.95 (s, 1 H), 8.05 (d, J = 8.0 Hz, 2
H), 8.42 (dd, J = 7.7, 1.8 Hz, 1 H) ppm. 13C NMR (100 MHz, CDCl3):
δ = 55.4, 111.0, 117.1, 120.8, 123.1, 126.5, 128.8, 128.9, 129.7, 130.2,
133.8, 151.8, 156.8, 165.6 ppm. HRMS (ESI) Calcd for C16H14ONS [M
+ H]+ = 268.0791, Found = 268.0786.
4-(4′-Isopropylphenyl)-2-phenylthiazole (3a): Yield: 463.8 mg
(83 %); white solid; Mp: 81–83 °C. IR (neat): ν = 3091, 1476, 834,
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756 cm–1, H NMR (400 MHz, CDCl3): δ = 1.28 (d, J = 6.8 Hz, 6 H),
2.95 (septet, J = 6.8 Hz, 1 H), 7.30 (d, J = 7.7 Hz, 2 H), 7.42 (s, 1 H),
7.42–7.49 (m, 3 H), 7.91 (d, J = 7.7 Hz, 2 H), 8.04 (d, J = 8.1 Hz, 2 H)
ppm. 13C NMR (100 MHz, CDCl3): δ = 23.9, 33.9, 111.9, 126.4, 126.5,
126.7, 128.8, 129.9, 132.1, 133.7, 148.9, 156.3, 167.6 ppm. HRMS (ESI)
Calcd for C18H18NS [M + H]+ = 280.1154, Found = 280.1150.
4-(2′-Methoxy-5′-methylphenyl)-2-phenylthiazole (3h): Yield:
337.6 mg (60 %); white solid; Mp: 64 °C. IR (neat): ν = 2911, 1493,
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806, 755 cm–1. H NMR (400 MHz, CDCl3): δ = 2.39 (s, 3 H), 3.94 (s,
3 H), 6.91 (d, J = 8.3 Hz, 1 H), 7.11 (d, J = 8.3 Hz, 1 H), 7.42–7.48 (m,
3 H), 7.94 (s, 1 H), 8.06 (d, J = 7.6 Hz, 2 H), 8.22 (s, 1 H) ppm. 13C
NMR (100 MHz, CDCl3): δ = 20.6, 55.5, 111.0, 117.0, 122.7, 126.6,
128.8, 129.2, 129.7, 130.0, 130.6, 133.9, 151.9, 154.8, 165.6 ppm.
HRMS (ESI) Calcd for C17H16ONS [M + H]+ = 282.0947, Found =
282.0944.
4-(4′-Methylphenyl)-2-phenylthiazole (3b):[16a]: Yield: 477.5 mg
(95 %); white solid; Mp: 110 °C. IR (neat): ν = 1480, 820, 763 cm–1
.
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1H NMR (400 MHz, CDCl3): δ = 2.40 (s, 3 H), 7.26 (d, J = 7.2 Hz, 2 H),
7.42 (s, 1 H), 7.42–7.48 (m, 3 H), 7.89 (d, J = 8.1 Hz, 2 H), 8.04 (d, J =
8.1 Hz, 2 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 21.9, 111.8, 126.3,
126.5, 128.8, 129.3, 129.9, 131.7, 133.7, 137.9, 156.3, 167.6 ppm.
HRMS (ESI) Calcd for C16H14NS [M + H]+ = 252.0841, Found =
252.0840.
4-(4′-Ethoxyphenyl)-2-phenylthiazole (3i): Yield: 292.6 mg (52 %);
white solid; Mp: 135–136 °C. IR (neat): ν = 1473, 1247, 839, 766 cm–1
.
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1H NMR (400 MHz, CDCl3): δ = 1.44 (t, J = 6.8 Hz, 3 H), 4.09 (q, J =
6.8 Hz, 2 H), 6.97 (d, J = 8.8 Hz, 2 H), 7.34 (s, 1 H), 7.42–7.48 (m, 3
H), 7.92 (d, J = 8.8 Hz, 2 H), 8.04 (d, J = 8.1 Hz, 2 H) ppm. 13C NMR
(100 MHz, CDCl3): δ = 14.8, 63.4, 110.8, 114.5, 126.5, 127.3, 127.6,
128.8, 129.9, 133.8, 156.1, 158.9, 167.6 ppm. HRMS (ESI) Calcd for
4-(4′-tert-Butylphenyl)-2-phenylthiazole (3c): Yield: 498.8 mg
(85 %); white solid; Mp: 62–63 °C. IR (neat): ν = 2964, 1475, 831,
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763 cm–1. H NMR (400 MHz, CDCl3): δ = 1.36 (s, 9 H), 7.43 (s, 1 H),
C
17H16ONS [M + H]+ = 282.0947, Found = 282.0946.
4-(2′-Ethoxyphenyl)-2-phenylthiazole (3i′): Yield: 50.6 mg (9 %);
white solid; Mp: 67–69 °C. IR (neat): ν = 1474, 1238, 852, 751 cm–1
7.43–7.48 (m, 5 H), 7.92 (d, J = 8.6 Hz, 2 H), 8.04 (d, J = 7.8 Hz, 2 H)
ppm. 13C NMR (100 MHz, CDCl3): δ = 31.2, 34.6, 111.9, 125.6, 126.1,
126.5, 128.8, 129.9, 131.7, 133.7, 151.1, 156.3, 167.6 ppm. HRMS (ESI)
Calcd for C19H20NS [M + H]+ = 294.1311, Found = 294.1310.
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1H NMR (400 MHz, CDCl3): δ = 1.56 (t, J = 6.8 Hz, 3 H), 4.20 (q, J =
6.8 Hz, 2 H), 7.00 (d, J = 8.1 Hz, 1 H), 7.08 (td, J = 7.5, 1.1 Hz, 1 H),
7.29 (td, J = 7.7, 1.8 Hz, 1 H), 7.42–7.48 (m, 3 H), 8.02 (s, 1 H), 8.06
(d, J = 7.9 Hz, 2 H), 8.46 (dd, J = 7.7, 1.8 Hz, 1 H) ppm. 13C NMR
(100 MHz, CDCl3): δ = 15.0, 63.9, 111.8, 117.0, 120.7, 123.0, 126.6,
128.6, 128.8, 129.7, 130.2, 133.9, 151.9, 156.2, 165.5 ppm. HRMS (ESI)
Calcd for C17H16ONS[M + H]+ = 282.0947, Found = 282.0945.
4-(1′,1′′-Biphenyl)-4′-yl-2-phenylthiazole (3d): Yield: 532.8 mg
(85 %); white solid; Mp: 159–160 °C. IR (neat): ν = 1472, 1404, 846,
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759, 742 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 7.43–7.50 (m, 5 H),
7.52 (s, 1 H), 7.37 (m, 1 H), 7.65–7.71 (m, 4 H), 8.04–8.09 (m, 4 H)
ppm. 13C NMR (100 MHz, CDCl3): δ = 112.6, 126.6, 126.8, 126.9,
127.4 (2 C), 128.8, 128.9, 130.0, 133.4, 133.7, 140.6, 140.8, 155.9,
167.9 ppm. HRMS (ESI) Calcd for C21H16ONS [M + H]+ = 314.0998,
Found = 314.0993.
4-(2′,5′-Dimethoxyphenyl)-2-phenylthiazole (3j): Yield: 356.8 mg
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(60 %); yellow oil. IR (neat): ν = 2953, 1492, 800, 763 cm–1. H NMR
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(400 MHz, CDCl3): δ = 3.88 (s, 3 H), 3.93 (s, 3 H), 6.86 (dd, J = 8.8,
3.1 Hz, 1 H), 6.94 (d, J = 8.8 Hz, 1 H), 7.42–7.48 (m, 3 H), 7.99 (s, 1
H), 8.03–8.06 (m, 3 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 55.8,
56.0, 112.4, 114.2, 115.2, 117.4, 123.8, 126.6, 128.8, 129.8, 133.8,
151.3, 151.6, 153.7, 165.6 ppm. HRMS (ESI) Calcd for C17H16O2NS [M
+ H]+ = 298.0896, Found = 298.0892.
4-(2′,5′-Dimethylphenyl)-2-phenylthiazole (3e): Yield: 477.6 mg
(90 %); pale pink oil. IR (neat): ν = 2918, 1473, 816, 761 cm–1 1H
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NMR (400 MHz, CDCl3): δ = 2.36 (s,3 H), 2.48 (s, 3 H), 7.08 (d, J =
7.9 Hz, 1 H), 7.11 (s, 1 H), 7.22 (s, 1 H), 7.41–7.47 (m, 3 H), 7.56 (d,
J = 7.9 Hz, 1 H), 8.02 (d, J = 7.7 Hz, 2 H) ppm. 13C NMR (100 MHz,
CDCl3): δ = 21.1, 21.1, 115.2, 126.5, 126.6, 128.8, 129.7, 129.8, 131.6,
131.7, 133.7, 136.0, 137.9, 156.6, 166.6 ppm. HRMS (ESI) Calcd for
C17H16NS [M + H]+ = 266.0998, Found = 266.0994.
4-(2′,4′-Dimethoxyphenyl)-2-phenylthiazole (3k): Yield: 362.7 mg
(61 %); colorless oil. IR (neat): ν = 1483, 1207, 827, 761 cm–1 1H
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NMR (400 MHz, CDCl3): δ = 3.87 (s, 3 H), 3.95 (s, 3 H), 6.57 (d, J =
2.5 Hz, 1 H), 6.57 (dd, J = 8.6, 2.5 Hz, 1 H), 7.41–7.47 (m, 3 H), 7.80
(s, 1 H), 8.04 (d, J = 7.9 Hz, 2 H), 8.35 (d, J = 8.6 Hz, 1 H) ppm. 13C
NMR (100 MHz, CDCl3): δ = 55.3, 98.6, 104.6, 115.0, 116.6, 126.5 (2
C), 128.7, 129.6, 131.0, 133.9, 151.8, 157.9, 160.3, 165.4 ppm. HRMS
(APCI) Calcd for C17H16O2NS [M + H]+ = 298.0896, Found =
298.0893.
2-Phenyl-4-(3′,4′,5′-trimethylphenyl)thiazole
(3f):
Yield:
491.7 mg (88 %); white solid; Mp: 83–85 °C. IR (neat): ν = 2915,
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1473, 801, 762, cm–1
.
1H NMR (400 MHz, CDCl3): δ = 2.21 (s, 3 H),
2.40 (s, 6 H), 7.40 (s, 1 H), 7.42–7.48 (m, 3 H), 7.63 (s, 2 H), 8.04 (d,
J = 7.7 Hz, 2 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 15.3, 20.7,
111.7, 125.5, 126.6, 128.8, 129.9, 131.4, 133.8, 135.2, 136.7, 156.6,
167.5 ppm. HRMS (ESI) Calcd for C18H18NS [M + H]+ = 280.1154,
Found = 280.1154.
4-(2′,3′-Dihydrobenzofuran-5′-yl)-2-phenylthiazole (3l): Yield:
419.0 mg (75 %); white solid; Mp: 99–100 °C. IR (neat): ν = 3130,
4-(4′-Methoxyphenyl)-2-phenylthiazole (3g): Yield: 326.1 mg
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1477, 1234, 823, 749 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 3.28 (t,
(61 %); white solid; Mp: 125 °C. IR (neat): ν = 3110, 1480, 1248, 835,
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761 cm–1. H NMR (400 MHz, CDCl3): δ = 3.86 (s, 3 H), 6.98 (d, J =
J = 8.8 Hz, 2 H), 4.63 (t, J = 8.8 Hz, 2 H), 6.85 (d, J = 8.2 Hz, 1 H),
7.30 (s, 1 H), 7.42–7.48 (m, 3 H), 7.74 (d, J = 8.2 Hz, 1 H), 7.88 (s, 1
H), 8.03 (d, J = 7.9 Hz, 2 H) ppm. 13C NMR (100 MHz, CDCl3): δ =
29.6, 71.5, 109.3, 110.4, 123.3, 126.5 (2 C), 126.6, 127.5, 128.8, 129.9,
133.8, 156.4, 160.2, 167.5 ppm. HRMS (APCI) Calcd for C17H14ONS
[M + H]+ = 280.0791, Found = 280.0787.
8.8 Hz, 2 H), 7.34 (s, 1 H), 7.45 (m, 3 H), 7.93 (d, J = 8.8 Hz, 2 H),
7.04 (d, J = 8.1 Hz, 2 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 55.3,
110.8, 114.0, 126.5, 127.4, 127.7, 128.8, 129.9, 133.8, 156.0, 159.6,
167.6 ppm. HRMS (ESI) Calcd for C16H14ONS [M + H]+ = 268.0791,
Found = 268.0791.
4-(2′-Methoxyphenyl)-2-phenylthiazole (3g′): Yield: 144.3 mg
4-(4′-Fluorophenyl)-2-phenylthiazole (3m): Yield: 434.0 mg
(27 %); white solid; Mp: 84–85 °C. IR (neat): ν = 1485, 1239, 852, (85 %); white solid; Mp: 97–98 °C. IR (neat): ν = 1507, 1480, 831,
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Eur. J. Org. Chem. 0000, 0–0
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© 0000 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim