S. K. Sabui, R. V. Venkateswaran / Tetrahedron Letters 45 (2004) 9653–9655
9655
4. Tuhina, K.; Bhowmik, D. R.; Venkateswaran, R. V. Chem.
Commun. 2002, 634–635.
124.7, 125.9, 130.0, 135.7, 140.3, 152.9; Anal. Calcd for
C14H20O: C, 82.35; H, 9.80. Found: C, 82.13; H, 9.51. For
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5. Sabui, S. K.; Mondal, P.; Venkateswaran, R. V. J. Chem.
Res. (S) 2002, 428–429.
6. Spectral, analytical data of 5, 7, 10, 11, 17, 18. For 5: IR
11: IR (CHCl3) 1668cmÀ1; H NMR (300MHz, CDCl3) d
1.36 (br s, 6H), 1.41–1.57 (m, 4H), 1.88–1.94 (m, 2H), 2.36
(s, 3H), 6.82 (s, 1H), 7.01 (d, J 8.0Hz, 1H), 7.95 (d, J
8.0Hz, 1H); 13C NMR (75MHz, CDCl3) d 20.7, 21.3, 26.8,
29.5, 32.7, 39.9, 80.5, 125.1, 127.8, 129.4, 131.1, 145.1,
155.2, 200.7; Anal. Calcd for C14H18O2: C, 77.06; H, 8.25.
Found: C, 76.83; H, 7.92. For 17: 1H NMR (300MHz,
CDCl3) d 1.28 (s, 3H), 1.35–1.55 (m, 3H), 1.44 (s, 3H),
1.59–1.75 (m, 2H), 2.13–2.19 (m, 1H), 2.31 (s, 3H), 3.38 (s,
3H), 4.55 (ABq, J 6.5Hz, 2H), 4.97 (dd, J 2.8, 10.4Hz, 1H),
6.74 (s, 1H), 6.97 (d, J 7.7Hz, 1H), 7.31 (d, J 7.8Hz, 1H);
13C NMR (75MHz, CDCl3) d 20.1, 21.4, 27.6, 28.8, 38.0,
38.7, 55.9, 73.9, 81.8, 94.9, 125.5 (2C), 126.0, 135.2, 137.2,
152.6; Anal. Calcd for C16H24O3: C, 72.72; H, 9.09. Found:
C, 72.33; H,8.85. For 18: 1H NMR (300MHz, CDCl3) d
1.30 (s, 6H), 1.38–1.56 (m, 2H), 1.75–1.84 (m, 2H), 2.29 (s,
3H),2.81 (t, J 6.5Hz, 2H), 4.92 (s, 1H), 5.42 (s, 1H), 6.72 (s,
1H), 6.88 (d, J 8.0Hz, 1H), 7.48 (d, J 8.0Hz, 1H); 13C
NMR (75MHz, CDCl3) d 21.1, 26.6, 27.7 (2C), 33.7, 34.1,
81.2, 113.0, 125.6, 127.4, 128.2, 129.9, 138.5, 147.4, 152.2;
Anal. Calcd for C15H20O: C, 83.33; H, 9.25. Found: C,
83.03; H, 8.91.
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(CHCl3) 1641cmÀ1; H NMR (300MHz, CDCl3) d 1.37 (t,
J 7.2Hz, 3H), 2.40 (s, 3H), 4.32 (q, J 7.2Hz, 2H), 6.45 (m,
2H), 6.96 (d, J 5.4Hz, 1H), 7.10 (d, J 7.8Hz, 1H), 7.44 (s,
1H), 7.81 (d, J 8.1Hz, 1H); 13C NMR (75MHz, CDCl3) d
14.6, 21.8, 62.3, 124.4, 124.5, 127.5, 128.1, 129.1, 132.0,
134.9, 146.5, 149.1, 158.7, 162.6, 191.2; Anal. Calcd for
C15H14O4: C, 69.76; H, 5.42. Found: C, 69.73; H, 5.38. For
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7: IR (CHCl3) 1745cmÀ1; H NMR (300MHz, CDCl3) d
1.33 (t, J 7.1Hz, 3H), 1.40–1.49 (m, 2H), 1.55 (s, 3H), 1.69–
1.93 (m, 4H), 2.27 (s, 3H), 2.53–2.60 (m, 1H), 2.74–2.82 (m,
1H), 4.29 (q, J 7.1Hz, 2H), 6.77 (s, 1H), 6.85 (d, J 7.3Hz,
1H), 6.99 (d, J 7.5Hz, 1H); 13C NMR (75MHz, CDCl3) d
14.1, 20.8, 24.4, 24.8, 30.8, 31.3, 33.6, 61.0, 85.3, 125.2,
125.5, 130.0,135.2, 136.1, 151.9, 173.6; Anal. Calcd for
C16H22O3: C, 73.28; H, 8.39. Found: C, 72.95; H, 8.03. For
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10: H NMR (300MHz, CDCl3) d 1.29 (s, 6H), 1.42–1.49
(m, 2H), 1.51–1.61 (m, 4H), 2.12 (s, 3H), 2.58–2.65 (m, 2H),
6.65 (s, 1H), 6.79 (m, 1H), 6.93 (d, J 3.0Hz, 1H); 13C NMR
(75MHz) d 20.9, 23.4, 27.6, 27.7, 31.1, 31.2, 37.4, 80.9,