Arkivoc 2019, v, 10-18
Mathew, E. M. et al.
147.0, 144.6, 142.5, 129.8, 125.5, 124.9, 123.5, 121.2, 68.2, 59.6, 52.2; MS: m/z 260 (M+); Anal. Calcd. for
C18H12O2: C: 83.06, H: 4.65. Found: C: 83.01, H: 4.62.
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Compound 5b. Yield 82 %, mp 175-178 °C; IR (νmax, cm-1): 1778, 1350, 750; H NMR (CDCl3): δ 7.52-7.01 (m,
8H), 6.43 (t, 1H, J 2.4 Hz), 5.03 (d, 2H, J 2.4 Hz), 2.23 (s, 3H); 13C NMR (CDCl3): δ 173.2, 147.5, 146.9, 143.5,
134.0, 125.2, 124.5, 120.8, 120.6, 68.0, 59.1, 51.3, 15.4; MS: m/z 274 (M+). Anal. Calcd. for C19H14O2: C: 83.19,
H: 5.14. Found: C: 83.10, H: 5.12.
Compound 5c. Yield 88 %, mp 200-202 °C; IR (νmax, cm-1): 1769, 1330, 750; H NMR (CDCl3): δ 7.44-6.93 (m,
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9H), 4.99 (d, 2H, J 2 Hz), 3.94 (s, 3H); 13C NMR (CDCl3): δ 172.6, 145.8, 144.8, 140.8, 127.9, 125.4, 124.9, 120.8,
120.7, 88.5, 67.9, 57.9, 55.2; MS: m/z 290 (M+); Anal. Calcd. for C19H14O3: C: 78.61, H: 4.86. Found: C: 78.52, H:
4.78.
Compound 5d. Yield 85 %, mp 274-276 °C; IR (νmax, cm-1): 1778, 1320, 750; 1H NMR (CDCl3): δ 7.70-6.94 (m,
14H), 5.11 (d, 2H, J 2.4 Hz); 13C NMR (CDCl3): δ 173.1, 149.1, 147.2, 142.9, 134.5, 130.0, 129.5, 128.7, 127.9,
124.9, 124.9, 123.8, 121.0, 68.1, 61.3, 59.8; MS: m/z 336 (M+); Anal. Calcd. for C24H16O2: C: 85.69, H:
4.79.Found: C: 85.61, H: 4.70.
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Compound 6a5. Yield 80 %, mp 129-132 °C; IR (νmax, cm-1): 1350, 750; H NMR (CDCl3): δ 7.30-6.95 (m, 8H),
6.66 (dt, 1H, J1 6 Hz, J2 1.6 Hz), 5.09 (d, 1H, J 6 Hz), 3.98 (s, 2H), 3.57 (d, 2H, J 1.6 Hz); 13C NMR (CDCl3): δ 155.3,
147.6, 145.8, 128.9, 124.6, 124.2, 122.9, 120.0, 64.2, 51.6, 33.4, 30.7; MS: m/z 262(M+); Anal. Calcd. for
C18H14S: C: 82.40, H: 5.38, S: 12.22. Found: C: 82.34, H: 5.37, S: 12.29.
Compound 6b. Yield 74 %, mp 112-114 °C; IR (νmax, cm-1): 2965, 1350, 750; 1H NMR (CDCl3): δ 7.29-7.00 (m,
8H), 6.29 (t, 1H, J 2 Hz), 3.98 (s, 2H), 3.58 (d, 2H, J 2 Hz), 2.16 (s, 3H); 13C NMR (CDCl3): δ 156.0, 149.9, 146.8,
133.3, 124.3, 124.0, 120.0, 119.6, 63.6, 49.9, 33.5, 31.0, 15.7; MS: m/z 276(M+); Anal. Calcd. for C19H16S: C:
82.56, H: 5.83, S: 11.61. Found: C: 82.51, H: 5.87, S: 11.62.
Compound 6c. Yield 78 %, mp 153-156 °C; IR (νmax, cm-1): 2936, 1350, 750; 1H NMR (CDCl3): δ 7.39-6.91 (m,
8H), 6.79 (t, 1H, J 2 Hz), 3.90 (s, 3H), 3.88 (s, 2H), 3.54 (d, 2H, J 2 Hz); 13C NMR (CDCl3): δ 153.1, 146.6, 143.2,
125.9, 123.5, 123.3, 118.9, 118.5, 86.2, 61.8, 53.9, 32.6, 29.8; MS: m/z 292(M+); Anal. Calcd. for C19H16OS: C:
78.05, H: 5.52, S: 10.97. Found: C: 78.01, H: 5.44, S: 10.88.
Compound 6d. Yield 75 %, mp 218-221 °C; IR (νmax, cm-1): 1350, 750; 1H NMR (CDCl3): δ 7.71-6.89 (m, 14H),
4.06 (s, 2H), 3.66 (d, 2H, J 1.6 Hz); 13C NMR (CDCl3):- δ 157.4, 150.1, 146.1, 135.5, 130.2, 128.6, 128.5, 127.5,
124.3, 124.0, 123.1, 119.9, 63.8, 60.0, 33.9, 31.2; MS: m/z 338(M+); Anal. Calcd. for C24H18S: C: 85.17, H: 5.36, S:
9.47. Found: C: 85.08, H: 5.38, S: 9.54.
Compound 7. Yield 78 %, mp 129-132 °C; IR (νmax, cm-1): 1318, 1300, 750; 1H NMR (CDCl3): δ 7.26 -6.87 (m, 9H),
5.09 (d, 1H, J 6 Hz), 4.10 (s, 2H), 3.80 -3.73 (m, 2H); 13C NMR (CDCl3): δ 148.3, 145.6, 144.3, 134.4, 133.3, 119.4,
119.0, 118.7, 58.48, 53.9, 50.5, 50.2; MS: m/z 294(M+); Anal. Calcd. for C18H14O2S: C: 73.44, H: 4.79, S: 10.89.
Found: C: 73.41, H: 4.78, S: 10.91.
Compound 8a5. Yield 90 %, mp 198-200 °C; IR (νmax, cm-1): 2880, 1350, 750; 1H NMR (CDCl3): δ 7.29-6.97 (m,
8H), 6.61 (dt, 1H, J1 6 Hz, J2 2 Hz), 5.16 (d, 1H, J 6 Hz), 4.99 (s, 2H), 4.41 (d, 2H, J 2 Hz); 13C NMR (CDCl3): δ 154.9,
147.2, 145.1, 125.7, 124.6, 124.3, 123.0, 120.0, 67.5, 66.4, 62.1, 52.0; MS: m/z 246(M+); Anal. Calcd. for
C18H14O: C: 87.78, H: 5.73. Found: C: 87.76, H: 5.7.
Compound 8b. Yield 81 %, mp 139-142 °C; IR (νmax, cm-1): 2925, 1350, 750; 1H NMR (CDCl3): δ 7.32 -6.99 (m,
8H), 6.25 (t, 1H, J 2 Hz), 5.00 (s, 2H), 4.42 (d, 2H, J 2 Hz), 2.19 (s, 3H); 13C NMR (CDCl3): δ 154.5, 148.5, 145.1,
128.9, 123.4, 123.0, 119.0, 118.6, 66.53, 65.5, 60.5, 49.4, 14.7; MS: m/z 260(M+); Anal. Calcd. for C19H16O: C:
87.66, H: 6.19. Found: C: 87.62, H: 6.17.
Compound 8c. Yield 85 %, mp 155-158 °C; IR (νmax, cm-1): 2940, 1350, 750; 1H NMR (CDCl3): δ 7.49-6.98 (m,
8H), 6.83 (t, 1H, J 3 Hz ), 5.00 (s, 2H), 4.56 (d, 2H, J 3 Hz), 4.00 (s, 3H); 13C NMR (CDCl3): δ 153.7, 147.3, 143.6,
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