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PAPER
1H NMR (CDCl3): d = 7.43–6.68 (m, 15 H), 4.39 (t, J1 = 6 Hz,
J2 = 5.7 Hz, 1 H), 3.68 (s, 6 H), 3.58 (s, 3 H), 2.91–2.86 (m, 1 H),
2.67–2.54 (m, 2 H), 1.77–1.70 (m, 2 H), 1.18–1.11 (m, 2 H), 0.88–
0.85 (m, 3 H).
1H NMR (CDCl3): d = 5.90–5.80 (m, 6 H), 3.95 (uneven triplet,
J1 = 7.2 Hz, J2 = 8.1 Hz, 1 H), 2.72–2.67 (m, 1 H), 2.35–2.28 (m,
1 H), 2.11–2.06 (m, 1 H), 2.26, 2.22, 2.20 (3 × s, 3 × 3 H), 1.22 (d,
J = 6.9 Hz, 3 H).
13C NMR (CDCl3): d = 137.3, 137.2, 127.8, 127.4, 126.5, 126.1,
125.9, 121.2, 119.9, 119.7, 118.9, 118.5, 118.3, 118.2, 109.0, 108.9,
42.9, 39.3, 34.9, 32.6, 32.5, 31.8, 20.9.
13C NMR (CDCl3): d = 157.7, 153.8, 153.7, 150.4, 150.5, 149.9,
106.5, 105.9, 104.6, 38.6, 36.8, 30.9, 19.5, 13.5.
HRMS (EI): m/z calcd for C19H22O3: 298.1569; found: 298.1521.
HRMS (EI): m/z calcd for C33H35N3: 473.2831; found: 473.2816.
6d
7g
Yield: 47%; colorless liquid.
Yield: 73%; colorless viscous liquid.
IR (KBr): 3413, 1600, 1545, 1455, 1415, 1335, 964, 739 cm–1.
IR (thin film): 2958, 2924, 1615, 1562, 1450, 1382, 1216, 1017,
958, 783 cm–1.
1H NMR (CDCl3): d = 5.97–5.79 (m, 6 H), 3.85 (uneven triplet,
J1 = 6.6 Hz, J2 = 8.7 Hz, 1 H), 2.55–2.43 (m, 1 H), 2.22 (s, 9 H),
2.19–2.16 (m, 2 H), 1.64–1.42 (m, 2 H), 1.25–1.15 (m, 2 H), 0.82
(uneven triplet, J1 = 7.2 Hz, J2 = 7.5 Hz, 3 H).
13C NMR (CDCl3): d = 155.8, 154.5, 153.4, 151.3, 150.7, 150.5,
107.4, 107.0, 106.6, 106.4, 106.2, 105.9, 105.8, 105.5, 37.5, 37.1,
36.9, 36.7, 36.2, 20.5, 14.2.
1H NMR (CDCl3): d = 7.84–6.87 (m, 15 H), 6.77 (s, 2 H), 6.68 (d,
J = 6.0 Hz, 1 H), 5.37 (d, J = 7.2 Hz, 1 H).
13C NMR (CDCl3): d = 139.9, 138.8, 137.7, 136.6, 132.3, 129.9,
128.4, 126.9, 126.3, 122.6, 121.9, 119.9, 119.3, 118.2, 117.2, 111.1,
37.4.
HRMS (EI): m/z calcd for C25H19ClN2: 382.1237; found: 382.1237.
Acknowledgment
HRMS (EI): m/z calcd for C21H 26O3: 326.1882; found: 326.1841.
Financial assistance from the Council of Scientific and Industrial
Research (CSIR), Government of India, is acknowledged. The au-
thors also thank Mrs. Saumini Mathew for recording NMR spectra
and Mrs. S. Viji for mass spectral analysis.
7i
Yield: 75%; pale-pink amorphous solid.
IR (KBr): 2934, 1610, 1542, 1479, 1464, 1421, 1367, 1323, 1260,
1153, 735 cm–1.
1H NMR (CDCl3): d = 7.45–6.76 (m, 18 H), 4.50–4.44 (m, 2 H),
3.71 (s, 6 H), 3.67 (s, 3 H), 3.08–2.92 (m, 2 H).
13C NMR (CDCl3): d = 150.2, 137.3, 127.5, 126.1, 126.4, 126.3,
126.2, 124.1, 123.1, 121.6, 121.4, 121.4, 120.0, 119.9, 119.8, 119.7,
118.7, 118.5, 118.2, 109.1, 109.0, 43.8, 36.3, 32.7, 31.7.
References
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Angew. Chem. Int. Ed. 2000, 39, 2285.
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3485. (b) Shi, Z.; He, C. J. Org. Chem. 2004, 69, 3669.
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X.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 6884.
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39, 4237. (b) Hashmi, A. S. K. Gold Bull. 2003, 36, 3.
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HRMS (FAB): m/z calcd for C34H31N3S: 513.22; found: 513.21.
6c
Yield: 23%; pale-pink viscous liquid.
IR (thin film): 3415, 1644, 1538, 1459, 1245, 1168, 1027 cm–1.
1H NMR (CDCl3): d = 7.69–6.68 (m, 16 H), 6.59–6.52 (dd, J1 = 6.9
Hz, J2 = 6.6 Hz, 1 H), 6.38 (d, J = 15.6 Hz, 1 H), 5.28 (d, J = 6.6 Hz,
1 H), 3.71 (s, 3 H).
13C NMR (CDCl3): d = 160.4, 137.2, 136.5, 133.0, 129.1, 126.2,
125.7, 121.8, 120.4, 119.8, 118.9, 111.2, 54.9, 39.9.
(6) (a) Nair, V.; Thomas, S.; Mathew, S. C. Org. Lett. 2004, 6,
3513. (b) Nair, V.; Thomas, S.; Mathew, S. C.; Vidya, N.;
Rath, N. P. Tetrahedron 2005, 61, 9533.
HRMS (FAB): m/z calcd for C26H22N2O: 378.17; found: 378.20.
(7) Gomberg, M. J. Am. Chem. Soc. 1900, 22, 757.
(8) Nair, V.; Thomas, S.; Mathew, S. C.; Abhilash, K. G.
Tetrahedron 2006, 62, 6731.
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Application of Dyes; Wiley-Interscience: New York, 1972.
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58, 4376.
7j
Yield: 37%; pale-pink amorphous solid.
IR (KBr): 3411, 1606, 1508, 1455, 1416, 1333, 1241, 740 cm–1.
1H NMR (CDCl3): d = 7.04–6.32 (m, 22 H), 4.30 (uneven triplet,
J1 = 6 Hz, J2 = 8.4 Hz, 1 H), 4.13–4.02 (m, 2 H), 4.10 (t, J = 7.2 Hz,
1 H), 3.63 (s, 3 H).
13 C NMR (CDCl3): d = 157.8, 137.2, 136.5, 136.4, 129.1, 127.1,
126.8, 126.7, 121.8, 121.7, 120.4, 119.8, 119.6, 119.4, 118.8, 118.9,
113.7, 111.2, 111.1, 60.4, 55.0, 42.3, 39.7, 31.4.
(11) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic
Synthesis, 3rd Ed.; Wiley: New York, 1999.
(12) (a) Aldag, R. Photochromism based on dissociation
processes, In Photochromism: Molecules and Systems; Dürr,
H.; Bouas-Laurent, H., Eds.; Elsevier: London, 1990.
(b) Irie, M. J. Am. Chem. Soc. 1983, 105, 2078.
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1377. (b) Ungnade, H. E.; Crandall, E. W. J. Am. Chem. Soc.
1949, 71, 2209. (c) Pratt, E. F.; Green, L. Q. J. Am. Chem.
Soc. 1953, 75, 275.
HRMS (FAB): m/z [M + Na]+ calcd for C34H29N3ONa: 518.23;
found: 518.43.
7k
Yield: 77%; colorless liquid;
IR (thin film): 3109, 2929, 1562, 1455, 1221, 1022, 949, 783 cm–1.
Synthesis 2006, No. 21, 3647–3653 © Thieme Stuttgart · New York