A. Z. Halimehjani et al. / Tetrahedron Letters 50 (2009) 1441–1443
1443
Kitamura, T. Tetrahedron 2005, 61, 9291; (c) Nakazawa, T.; Furukawa, H.; Torii,
K.; Itabashi, K. Nippon Kagaku Kaishi 1989, 244.
9. Saidi, M. R.; Azizi, N. Tetrahedron: Asymmetry 2003, 14, 389.
115.4, 123.4, 124.3, 125.0, 125.5, 129.4, 130.3, 134.5, 143.5, 153.8, 156.5 ppm.
Table 2, entry 4: IR (KBr): = 3440, 1632, 1547, 1516, 1458, 1366, 1259, 1180,
1012 cmÀ1 1H NMR (500 MHz, CDCl3/DMSO): d = 5.28–5.34 (m, 2H), 5.58 (t,
m
;
10. Liu, T.-Y.; Cui, H.-L.; Chai, O.; Long, J.; Li, B.-J.; Wu, Y.; Ding, L.-S.; Chen, Y.-C.
Chem. Commun. 2007, 2228.
J = 7.5 Hz, 1H), 7.01–7.16 (m, 6H), 7.25–7.31 (m, 3H), 7.42 (d, J = 7.8 Hz, 1H),
7.79 (d, J = 8.5 Hz, 1H), 9.81 (br s, 1H, –OH) ppm; 13C NMR (125 MHz, CDCl3/
DMSO), d, 41.9, 78.5, 110.0, 117.7, 122.5, 123.6, 124.2, 127.2, 127.3, 128.0,
128.2, 128.9, 129.9, 140.7, 145.8, 146.2 ppm. Decomposed at 150 °C. Anal.
Calcd for C18H15NO4: C, 69.90; H, 4.85; N, 4.53. Found: C, 69.45; H, 4.66; N,
4.58.
11. (a) Ziyaei, A.; Saidi, M. R. Tetrahedron Lett. 2008, 49, 1244; (b) Azizi, N.;
Arynasab, F.; Saidi, M. R. Org. Biomol. Chem. 2006, 4, 4275; (c) Azizi, N.; Torkian,
L.; Saidi, M. R. J. Mol. Catal. A: Chem. 2007, 275, 109; (d) Ziyaei-Halimjani, A.;
Saidi, M. R. Can. J. Chem. 2006, , 84, 1515; (e) Azizi, N.; Aryanadab, F.; Torkian,
L.; Ziyaei-Halimehjani, A.; Saidi, M. R. J. Org. Chem. 2006, 71, 3634.
12. Azizi, N.; Saidi, M. R. Org. Lett. 2006, 7, 3649.
13. General procedure for the reaction of naphthol derivatives with nitrostyrene: In a
round-bottomed flask equipped with a magnetic stirrer, naphthol, nitrostyrene
(as noted in Table 2), and water (3 mL) were added. The mixture was stirred at
room temperature, and the progress of the reaction was monitored by TLC
(silica gel, ethyl acetate: petroleum ether 1:3). After completion of the reaction
(8 h), the products were extracted with ethyl acetate (2 Â10 mL). Evaporation
of the solvent gave a crude product. Purification was accomplished by washing
with hot petroleum ether (Table 2, entries 1, 4, 9, and 12) or using column
chromatography (silica gel, ethyl acetate: petroleum ether 1:3).
Table 2, entry 6: 1H NMR (500 MHz, CDCl3/DMSO), d, 5.08–5.23 (m, 3H), 6.55–
6.65 (m, 2H), 6.9 (m, 3H), 7.10–7.23 (m, 5H), 8.99 (br s, 1H), 9.17 (br s, 1H)
ppm; 13C NMR (125 MHz, CDCl3/DMSO), d, 40.3, 79.2, 104.9, 115.3, 115.6,
115.8, 123.7, 126.8, 128.0, 128.5, 129.3, 130.4, 135.1, 140.7, 155.7, 156.5 ppm.
Table 2, entry 9: IR (KBr):
m = 3515, 3412, 1635, 1551, 1379, 1280, 1182,
1015 cmÀ1 1H NMR (500 MHz, CDCl3/DMSO), d, 4.96 (dd, J = 13.2, 6.9 Hz, 1H),
;
5.21 (dd, J = 13.2, 7.6 Hz, 1H), 5.62 (t, J = 7.1 Hz, 1H), 5.79 (d, J = 2.7 Hz, 1H), 6.0
(t, J = 7.2 Hz, 1H), 6.92 (s, 1H), 6.96–7.03 (m, 2H), 7.05 (s, 1H), 7.31 (d, J = 7.9 Hz,
1H), 7.58 (d, J = 8.3 Hz, 1H), 7.7 (br s, 1H, OH), 9.81 (br s, 1H, OH) ppm; 13C NMR
(125 MHz, CDCl3/DMSO), d, 35.9, 77.0, 106.9, 110.3, 111.1, 115.2, 122.5, 123.5,
124.1, 127.3, 127.9, 129.8, 141.8, 146.2, 146.3, 153.5 ppm. Decomposed at
172 °C. Anal. Calcd For C16H13NO5: C, 64.21; H, 4.35; N, 4.68. Found: C, 63.98;
H, 3.90; N, 4.54.
Selected spectroscopic data: Table 2, entry 1: IR (KBr):
m = 3422, 1638, 1549,
1377, 1259, 1184, 1008 cmÀ1 1H NMR (500 MHz, CDCl3/DMSO), d, 5.20–5.30
;
(m, 2H), 5.71 (t, J = 7.4 Hz, 1H), 6.66 (dd, J = 4.9, 3.6 Hz, 1H), 6.81 (d, J = 3.3 Hz,
1H), 6.90 (d, J = 5.1 Hz, 1H), 6.97 (s, 1H), 7.04–7.11 (m, 2H), 7.37 (d, J = 8.0 Hz,
1H), 7.60 (br, 1H, –OH), 7.73 (d, J = 8.4 Hz, 1H), 9.85 (br s, 1H, –OH) ppm; 13C
NMR (125 MHz, CDCl3/DMSO), d, 37.2, 78.9, 109.9, 116.8, 121.8, 123.2, 123.9,
124.3, 125.0, 126.6, 126.9, 127.2, 129.4, 142.5, 145.5, 145.7 ppm.Decomposed
at 130 °C. Anal. Calcd for C16H13NO4S: C, 60.95; H, 4.12; N, 4.44. Found: C,
60.40; H, 3.90; N, 4.54.
Table 2, entry 11: 1H NMR (500 MHz, CDCl3/DMSO): d = 5.0 (dd, J = 13.3, 6.9 Hz,
1H), 5.40 (dd, J = 13.2, 8.1 Hz, 1H), 5.75 (t, J = 7.3 Hz, 1H), 5.93 (d, J = 3.1 Hz,
1H), 6.14 (t, J = 2.42 Hz, 1H), 6.80–6.85 (m, 3H), 6.9 (s, 1H), 6.95 (s, 1H), 7.41 (d,
J = 8.7 Hz, 1H), 7.46 (d, J = 8.7 Hz, 1H), 9.3 (br s, 1H, OH) ppm; 13C NMR
(125 MHz, CDCl3/DMSO), d, 35.6, 76.9, 104.6, 106.5, 110.7, 112.6, 115.4, 115.5,
123.6, 129.5, 130.5, 134.9, 141.2, 153.5, 154.3, 156.3 ppm.
Table 2, entry 14: 1H NMR (500 MHz, CDCl3/DMSO), d, 5.14 (dd, J = 12.9, 7.0 Hz,
1H), 5.16–5.36 (m, 2H), 6.50–6.80 (m, 2H), 7.03 (d, J = 7.7, 2.3 Hz, 2H), 7.24 (m,
3H), 7.34 (d, J = 8.7 Hz, 1H), 7.40 (d, J = 8.7 Hz, 1H), 9.0 (br s, 1H, OH), 9.2 (br s,
1H, OH) ppm; 13C NMR (125 MHz, CDCl3/DMSO), d, 40.5, 79.1, 104.9, 115.2,
115.5, 115.8, 123.9, 128.7, 129.4, 129.6, 130.6, 132.5, 135.0, 139.5, 154.0,
156.7 ppm.
Table 2, entry 3: 1H NMR (500 MHz, CDCl3/DMSO), d, 4.85 (dd, J = 13.0 Hz, 6.7,
1H) 4.96 (dd, J = 12.9, 7.7 Hz, 1H), 5.29 (t, J = 7.3 Hz, 1H), 6.35 (m, 2H), 6.44 (d,
J = 8.8 Hz, 1H), 6.51 (d, J = 3.2 Hz, 1H), 6.61 (d, J = 5.1 Hz, 1H), 6.82 (s, 1H), 6.99
(d, J = 8.7 Hz, 1H), 7.03 (d, J = 8.7 Hz, 1H), 8.99 (br s, 1H, OH), 9.36 (br s, 1H, OH)
ppm; 13C NMR (125 MHz, CDCl3/DMSO), d, 29.5, 79.2, 104.3, 114.7, 115.2,