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7. (a) Wohlleben, W. J. Ber. Dtsch. Chem. Ges. 1910, 42, 4369–4375; (b) Woo, L. W.
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E.; Frazer, M. G.; Frazer, V. S.; Washburn, L. C. Synthesis 1976, 621–623; (d)
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13. Compound 6a: mp 62–63 °C (lit.7f mp 78 °C); 1H NMR (300 MHz, CDCl3): d 3.96
(s, 3H), 6.77 (d, J = 9 Hz, 1H), 7.69 (dd, J = 2 and 9 Hz, 1H), 8.13 (d, J = 2 Hz, 1H);
13C NMR (75 MHz, CDCl3): d 52.6, 80.1, 114.5, 120.0, 138.3, 144.1, 161.2, 169.4;
GC/MS (EI) m/z (rel int.): 279 (7, (M+1)+), 278 (85, M+), 247 (17, ((M+1)–CH3O–
H)+), 246 (100, (M-CH3O–H)+), 219 (6), 218 (32), 191 (3), 190 (4), 151 (3,
(MÀI)+), 127 (3, I), 120 (3), 119 (3), 92 (8), 91 (9), 63 (22), 53 (8), 38 (2).
14. Compound 7a: mp 53–54 °C (lit.7g mp 54 °C); 1H NMR (300 MHz, CDCl3): d 5.57
(br s, 1H, OH), 6.78 (d, J = 9 Hz, 1H), 7.46 (dd, J = 2 and 9 Hz, 1H), 7.62 (d,
J = 2 Hz, 1H); 13C NMR (75 MHz, CDCl3): d 81.5, 118.2, 125.0, 136.9, 137.3,
151.4; GC/MS (EI) m/z (rel int.): 256 (32, (M+2)+), 254 (100, M+), 129 (8,
((M+2)-I)+), 127 (34, (MÀI)+), 99 (21), 91 (10), 73 (8), 63 (21).
15. Compound 7b: mp 82–84 °C (lit.7h mp 81–82 °C); 1H NMR (300 MHz, CDCl3): d
5.99 (s, 1H, OH), 7.46 (d, J = 2 Hz, 1H), 7.74 (d, J = 2 Hz, 1H); 13C NMR (75 MHz,
CDCl3): d 83.9, 112.9, 119.7, 132.0, 139.6, 150.4; GC/MS (EI) m/z (rel int.): 336
(26, (M+4)+), 334 (100, (M+2)+), 332 (78, M+), 305 (1, ((M+2)-CHO)+), 303 (1,
(M-CHO)+), 209 (1, ((M+4)-I)+), 207 (3, ((M+2)-I)+), 205 (2, (MÀI)+), 181 (6), 179
(26), 177 (19), 143 (6), 141 (7), 127 (9, I), 97 (13, (M-Br–I–CHO)+), 62 (20, (M-
Br–Cl–I–CHO)+), 53 (5).
16. Compound 8a: mp 75–76 °C (lit.7i mp 75–77 °C); 1H NMR (300 MHz, CDCl3): d
5.34 (s, 1H, OH), 6.91 (d, J = 9 Hz, 1H), 7.21 (dd, J = 2 and 9 Hz, 1H), 7.63(d,
J = 2 Hz, 1H); 13C NMR (75 MHz, CDCl3): d 85.4, 115.7, 126.1, 130.1, 137.2, 153.8;
GC/MS (EI) m/z (rel int.): 256 (33, (M+2)+), 254 (100, M+), 225 (1, (M-CHO)+), 129
(4, ((M+2)-I)+), 127 (19, (MÀI)+), 101 (7), 99 (23), 73 (7), 63 (15), 53 (4).
17. Compound 9a: mp 49–50 °C (lit.7h mp 51 °C); 1H NMR (300 MHz, CDCl3): d 5.49
(s, 1H, OH), 6.71 (d, J = 9 Hz, 1H), 7.41 (dd, J = 2 and 9 Hz, 1H), 7.67 (d, J = 2 Hz,
1H); 13C NMR (75 MHz, CDCl3): d 81.0, 110.3, 117.1, 137.0, 138.6, 151.3; GC/MS
(EI) m/z (rel int.): 300 (98, (M+2)+), 298 (100, M+), 271 (1, ((M+2)-CHO)+), 269
(1, (M-CHO)+), 173 (16, ((M+2)-I)+), 171 (17, (MÀI)+), 145 (11), 143 (12), 127 (7,
I), 119 (3), 117 (3), 92 (19), 74 (3), 63 (28), 53 (8), 38 (3).
8. Compound 1a: mp 93 °C (lit.7a mp 93–94 °C); 1H NMR (300 MHz, CDCl3): d 5.10
(br s, 1H, OH), 6.62 (d, J = 9 Hz, 2H), 7.51 (d, J = 9 Hz, 2H); 13C NMR (75 MHz,
CDCl3): d 82.8, 117.8, 138.4, 155.2; GC/MS (EI) m/z (rel int.): 220 (100, M+), 191
(2, (M-CHO)+), 127 (4, I), 110 (4), 93 (26, (MÀI)+), 74 (2), 65 (23), 53 (3), 39 (10).
9. Compound 2a: colourless oil (lit.7b light-brown oil); 1H NMR (300 MHz, CDCl3):
d 2.24 (s, 3H), 5.17 (br s, 1H, OH), 6.87 (d, J = 8 Hz, 1H), 7.03 (d, J = 8 Hz, 1H),
7.47 (s, 1H); 13C NMR (75 MHz, CDCl3): d 19.9, 85.4, 114.7, 130.9, 131.9, 138.3,
152.6; GC/MS (EI) m/z (rel int.): 234 (100, M+), 127 (4, I), 107 (33, (MÀI)+), 77
(28), 63 (3), 51 (9), 39 (3).
10. Compound 3a: mp 65–67 °C (lit.7c mp 66.5–68 °C); 1H NMR (300 MHz, CDCl3): d
2.20 (s, 3H), 4.79 (br s, 1H, OH), 6.54 (d, J = 8 Hz, 1H), 7.35 (dd, J = 2 and 8 Hz,
1H), 7.43 (d, J = 2 Hz, 1H); 13C NMR (75 MHz, CDCl3): d 15.4, 82.6, 117.1, 126.7,
135.8, 139.5, 153.7; GC/MS (EI) m/z (rel int.): 234 (100, M+), 127 (4, I), 107 (20,
(MÀI)+), 77 (34), 63 (4), 51 (7), 39 (4).
18. Compound 10a: mp 92–93 °C (lit.7j mp 91–92 °C); 1H NMR (300 MHz, CDCl3): d
7.25 (d, J = 8 Hz, 1H), 7.38 (t, J = 8 Hz, 1H), 7.55 (t, J = 8 Hz, 1H), 7.74 (d, J = 8 Hz,
2H), 7.93 (d, J = 8 Hz, 1H); 13C NMR (75 MHz, CDCl3): d 86.2, 116.4, 124.2,
128.2, 128.3, 129.7, 130.3, 130.6, 134.8, 153.8; GC/MS (EI) m/z (rel int.): 270
(100, M+), 241 (2, (M-CHO)+), 143 (9, (MÀI)+), 127 (2, I), 115 (36), 89 (4), 74 (2),
63 (5) 39 (1).
11. Compound 4a: colourless oil (lit.7d mp 43 °C); 1H NMR (300 MHz, CDCl3): d 3.87
(s, 3H), 5.59 (s, 1H, OH), 6.68 (d, J = 8 Hz, 1H), 7.18 (dd, J = 2 and 8 Hz, 1H), 7.22
(d, J = 2 Hz, 1H); 13C NMR (75 MHz, CDCl3): d 56.2, 80.9, 116.5, 119.7, 130.4,
145.7, 147.4; GC/MS (EI) m/z (rel int.): 251 (8, (M+1)+), 250 (100, M+), 236 (3,
((M+1)–CH3)+), 235 (45, (M-CH3)+), 208 (1, ((M+1)-CH3–CO)+), 207 (20, (M-
CH3–CO)+), 123 (4, (MÀI)+), 108 (7, (MÀI -CH3)+), 94 (2), 80 (5), 79 (5), 63 (5),
52 (11).
19. Compound 11a: mp 78 °C (dec) (lit.20a mp 104–105 °C; lit.20b mp 104 °C); 1H
NMR (300 MHz, CDCl3): d 5.48 (br s, 1H, OH), 6.64 (d, J = 8 Hz, 1H), 7.55 (dt,
J = 2 and 8 Hz, 1H), 7.62 (dt, J = 2 and 8 Hz, 1H), 7.89 (d, J = 8 Hz, 1H), 8.06 (dd,
J = 1 and 8 Hz, 1H), 8.19 (dd, J = 1 and 8 Hz, 1H); 13C NMR (75 MHz, CDCl3): d
88.2, 108.2, 110.1, 122.3, 126.1, 128.3, 131.9, 135.1, 136.8, 152.4; GC/MS (EI) m/
z (rel int.): 270 (100, M+), 241 (3, (M-CHO)+), 207 (1), 144 (10, ((M+1)-I)+), 143
(11, (MÀI)+), 135 (5), 127 (3, I), 115 (52), 89 (7), 63 (7), 32 (5).
12. Compound 5a: mp 90 °C (lit.7e mp 91–92 °C); 1H NMR (300 MHz, CDCl3): d 2.64
(s, 3H), 6.78 (d, J = 9 Hz, 1H), 7.71 (dd, J = 2 and 9 Hz, 1H), 8.00 (d, J = 2 Hz, 1H),
12.18 (s, 1H, OH); 13C NMR (75 MHz, CDCl3): d 26.7, 79.7, 120.9, 139.2, 144.7,
152.7, 161.9, 203.5; GC/MS (EI) m/z (rel int.): 262 (100, M+), 247 (77, (M-CH3)+),
219 (14, (M-COCH3)+), 191 (4), 135 (3, (MÀI)+), 127 (3, I), 120 (7), 107 (3), 92
(12), 77 (5), 63 (12), 43 (12).
20. (a) Sket, B.; Zupet, P.; Zupan, M. J. Chem. Soc., Perkin Trans. 1 1989, 2279–2281;
(b) Sumi Mitra, S.; Sreekumar, K. React. Funct. Polym. 1997, 32, 281–291. At this
stage we are unable to explain the discrepancy between our melting point and
the literature melting points. The 1H NMR and MS data of 11a matched those
reported in the literature.