JOURNAL OF CHEMICAL RESEARCH 2011 123
J = 2.5 Hz), 5.26 (dd, 1H, J = 10.0 Hz and J = 7.0 Hz), 3.76 (s, 3H),
3.74−3.70 (m, 2H), 2.25 (s, 3H), 2.24 (s, 3H) 2.22 (s, 3H). IR(KBr):
3314, 3106, 2862, 2380, 1742, 1612, 1470 cm−1. Anal. Calcd for
C27H26N4O2: C, 73.95; H, 5.98; N, 12.78; Found: C, 73.97; H, 6.12;
N, 12.85%.
Anal. Calcd for C16H14N2O2: C, 72.16; H, 5.30; N, 10.52. Found: C,
72.19; H, 5.37; N, 10.48%.
1e: 1H NMR (500 MHz, DMSO-d6): δ (ppm) 8.05 (s, 1H), 7.86 (d,
2H, J = 8.5 Hz), 7.36 (dd, 1H, J = 1.5 Hz and J = 4.0 Hz), 7.30 (d, 2H,
J = 8.5 Hz), 6.95 (t, 1H, J = 2.0 Hz), 6.20 (dd, 1H, J = 2.0 Hz and J =
4.5 Hz), 3.98 (s, 3H), 2.90−2.85 (m, 1H), 1.23 (d, 6H, J = 7.0 Hz).
Anal. Calcd for C18H18N2O: C, 77.67; H, 6.52; N, 10.06. Found: C,
77.69; H, 6.43; N, 10.08%.
4g: 1H NMR (500 MHz, CDCl3): δ 7.95−7.90 (m, 2H), 7.31 (t, 1H,
J = 7.5 Hz), 7.23 (s, 1H), 7.20 (d, 1H, J = 8.0 Hz), 7.12 (t, 1H, J = 8.0
Hz), 6.86 (s, 1H), 6.76 (d, 1H, J = 8.0 Hz), 6.69 (s, 1H), 6.11 (t, 1H,
J = 2.5 Hz), 5.67 (dd, 1H, J = 4.5 Hz and J = 2.5 Hz), 5.39 (dd, 1H,
J = 9.5 Hz and J = 5.5 Hz), 3.75−3.69 (m, 4H), 3.55−3.50 (m, 1H),
2.32 (s, 3H), 2.18 (s, 3H), 2.05 (s, 3H). IR(KBr): 3310, 3108, 2857,
2360, 1749, 1614, 1465 cm−1. Anal. Calcd for C27H26N4O2: C, 73.95;
H, 5.98; N, 12.78; Found: C, 73.87; H, 5.91; N, 12.75%.
1f: 1H NMR (500 MHz, DMSO-d6): δ (ppm) 8.04 (s, 1H), 7.79 (d,
1H, J = 8.0 Hz), 7.76 (s, 1H), 7.35 (dd, 1H, J = 1.5 Hz and J = 4.0 Hz),
7.26 (d, 1H, J = 7.5 Hz), 6.95 (t, 1H, J = 1.5 Hz), 6.21 (dd, 1H, J = 2.5
Hz and J = 4.5 Hz), 3.97 (s, 3H), 2.34 (s, 3H), 2.33 (s, 3H). Anal.
Calcd for C17H16N2O: C, 77.25; H, 6.10; N, 10.60. Found: C, 77.19;
H, 6.19; N, 10.48%.
4h: 1H NMR (500 MHz, CDCl3): δ 8.50 (s, 1H), 8.16 (d, 1H, J = 7.5
Hz), 7.99−7.96 (m, 2H), 7.54 (t, 1H, J = 8.0 Hz), 7.34−7.31 (m, 1H),
7.25−7.23 (m, 1H), 7.18 (s, 1H), 6.70 (s, 1H), 6.66 (d, 1H, J = 7.5 Hz),
6.17(dd, 1H, J = 4.5 Hz and J = 2.5 Hz), 5.66 (dd, 1H, J = 4.5 Hz and
J = 2.5 Hz), 5.56 (dd, 1H, J = 10.0 Hz and J = 5.5 Hz), 3.83 (t, 1H,
J = 9.5 Hz), 3.80 (s, 3H), 3.70 (dd, 1H, J = 9.5 Hz and J = 6.0 Hz),
2.25 (s, 3H). IR(KBr): 3319, 3107, 2957, 2863, 2240, 1730, 1615,
1520, 1468 cm−1. Anal. Calcd for C25H21N5O4: C, 65.93; H, 4.65;
N, 15.38; Found: C, 65.88; H, 4.75; N, 15.40%.
1g: 1H NMR (500 MHz, DMSO-d6): δ (ppm) 8.36 (s, 1H), 8.20 (d,
1H, J = 8.0 Hz), 7.36 (dd, 1H, J = 1.5 Hz and J = 4.0 Hz), 7.15 (d, 1H,
J = 8.0 Hz), 7.15 (s, 1H), 6.96 (t, 1H, J = 1.5 Hz), 6.22 (dd, 1H, J = 2.5
Hz and J = 4.5 Hz), 3.99 (s, 3H), 2.40 (s, 3H), 2.38 (s, 3H). Anal.
Calcd for C17H16N2O: C, 77.25; H, 6.10; N, 10.60. Found: C, 77.32;
H, 6.09; N, 10.53%.
1h: 1H NMR (500 MHz, DMSO-d6): δ (ppm) 8.70 (s, 1H), 8.41 (d,
1H, J = 8.0 Hz), 8.39−8.37 (m, 1H), 8.11 (s, 1H), 7.73 (t, 1H, J = 8.0
Hz), 7.40 (dd, 1H, J = 1.5 Hz and J = 4.0 Hz), 7.01 (t, 1H, J = 1.5 Hz),
6.26 (dd, 1H, J = 2.5 Hz and J = 4.0 Hz), 4.00 (s, 3H). Anal. Calcd
for C15H11N3O3: C, 64.05; H, 3.94; N, 14.94. Found: C, 64.09; H, 3.87;
N, 14.93%.
4i: 1H NMR (500 MHz, CDCl3): δ 8.23 (s, 2H), 7.99 (s, 1H), 7.78
(s, 2H), 7.32−7.29 (m, 1H), 7.26−7.14 (m, 2H), 6.70 (t, 1H, J = 2.0
Hz), 6.66 (d, 1H, J = 7.5 Hz), 6.18 (dd, 1H, J = 5.0 Hz and J = 2.0 Hz),
5.66 (dd, 1H, J = 4.0 Hz and J = 2.0 Hz), 5.56 (dd, 1H, J = 10.0 Hz
and J = 6.0 Hz), 3.81 (t, 1H, J = 9.5 Hz), 3.79 (s, 3H), 3.68 (dd, 1H,
J = 10.0 Hz and J = 6.0 Hz), 2.24 (s, 3H). IR(KBr): 3325, 3092, 2972,
2867, 2235, 1724, 1618, 1523, 1470 cm−1.Anal. Calcd for C25H21N5O4:
C, 65.93; H, 4.65; N, 15.38; Found: C, 65.95; H, 4.71; N, 15.47%.
4j: 1H NMR (500 MHz, CDCl3): δ 8.00 (s, 1H), 7.85 (s, 1H), 7.44
(dd, 1H, J = 8.5 Hz and J = 2.0 Hz), 7.34−7.31 (m, 1H), 7.26 (s, 1H),
7.12 (t, 1H, J = 7.5 Hz), 6.76 (d, 1H, J = 8.0 Hz), 6.74 (s, 1H), 6.24
(dd, 1H, J = 4.5 Hz and J = 2.5 Hz), 5.73 (dd, 1H, J = 4.5 Hz and J =
2.5 Hz), 5.66 (dd, 1H, J = 9.5 Hz and J = 5.0 Hz), 5.30 (s, 1H), 3.81
(t, 1H, J = 9.5 Hz), 3.77(s, 3H), 3.47 (dd, 1H, J = 9.5 Hz and J = 5.0
Hz), 2.18 (s, 3H). IR(KBr): 3318, 3106, 2970, 2862, 2359, 1738,
1617, 1470 cm−1. Anal. Calcd for C25H20N4O2Cl2: C, 62.64; H, 4.21;
N, 11.69; Found: C, 62.69; H, 4.16; N, 11.77%.
1
1i: H NMR (500 MHz, DMSO-d6): δ (ppm) 8.36−8.34 (m, 2H),
8.14−8.10 (m, 3H), 7.40 (dd, 1H, J = 1.5 Hz and J = 4.5 Hz), 7.02
(t, 1H, J = 1.5 Hz), 6.26 (dd, 1H, J = 2.5 Hz and J = 4.0 Hz), 4.00 (s,
3H). Anal. Calcd for C15H11N3O3: C, 64.05; H, 3.94; N, 14.94. Found:
C, 64.11; H, 3.95; N, 14.87%.
1j: 1H NMR (500 MHz, DMSO-d6): δ (ppm) 8.36 (s, 1H), 8.20 (d,
1H, J = 8.5 Hz), 7.53 (d, 1H, J = 2.0 Hz), 7.41 (d, 1H, J = 8.5 Hz), 7.34
(dd, 1H, J = 1.5 Hz and J = 4.5 Hz), 7.00 (t, 1H, J = 2.0 Hz), 6.24 (dd,
1H, J = 2.5 Hz and J = 4.0 Hz), 3.99 (s, 3H). Anal. Calcd for
C15H10Cl2N2O: C, 59.04; H, 3.30; N, 9.18. Found: C, 59.09; H, 3.21;
N, 9.23%.
1k: 1H NMR (500 MHz, DMSO-d6): δ (ppm) 8.40 (s, 1H), 8.25 (s,
1H), 8.20 (dd, 1H, J = 1.5 Hz and J = 8.5 Hz), 7.96−7.93 (m, 2H), 7.89
(d, 1H, J = 8.0 Hz), 7.62 (t, 1H, J = 8.0 Hz), 7.56 (t, 1H, J = 8.0 Hz),
7.41 (dd, 1H, J = 1.5 Hz and J = 4.0 Hz), 6.98 (t, 1H, J = 1.5 Hz), 6.24
(dd, 1H, J = 2.5 Hz and J = 4.5 Hz), 4.00 (s, 3H). Anal. Calcd
for C19H14N2O: C, 79.70; H, 4.93; N, 9.78. Found: C, 79.79; H, 4.87;
N, 9.69%.
4k: 1H NMR (500 MHz, CDCl3): δ 8.14−8.04 (m, 2H), 7.85−7.81
(m, 3H), 7.76 (dd, 1H, J = 8.5 Hz and J = 2.0 Hz), 7.45 (dd, 2H, J =
6.5 Hz and J = 3.0 Hz), 7.33−7.29 (m, 1H), 7.26−7.19 (m, 2H), 6.68
(d, 1H, J = 7.5 Hz), 6.64 (t, 1H, J = 1.5 Hz), 6.13 (dd, 1H, J = 4.5 Hz
and J = 1.5 Hz), 5.58−5.53 (m, 2H), 3.86 (d, 2H, J = 8.5 Hz), 3.78
(s, 3H), 2.28 (s, 3H). IR(KBr): 3288, 3107, 2861, 2360, 1742, 1613,
1469, 1404, 1362 cm−1. Anal. Calcd for C29H24N4O2: C, 75.63; H, 5.25;
N, 12.17; Found: C, 75.66; H, 5.39; N, 12.13%.
This work was financially supported by the research founda-
tion of Hebei University of Science and Technology.
Synthesis of 1a–k: A mixture of 5 (0.45 g, 3 mmol), 6 (3 mmol) and
glycol monomethyl ether (10 mL) were refluxed for 2 h (the progress
was monitored by TLC). After completion of the reaction, the mixture
was allowed to cool to room temperature and the crude products
were precipitated. The crude product was chromatographed on
silica gel (200–300 mesh) using a mixture of petroleum ether and
dichloromethane as eluent to afford the pure product 1a–k.
Received 27 November 2010; accepted 4 January 2011
Paper 1000449 doi: 10.3184/174751911X556846
Published online: 10 February 2011
1a: 1H NMR (500 MHz, DMSO-d6): δ (ppm) 8.09 (s, 1H), 8.00−7.98
(m, 2H), 7.54−7.49 (m, 3H), 7.37 (dd, 1H, J = 1.5 Hz and J = 4.0 Hz),
6.97 (d, 1H, J = 1.5 Hz), 6.23 (dd, 1H, J = 2.5 Hz and J = 4.0 Hz), 3.98
(s, 3H). Anal. Calcd for C15H12N2O: C, 76.25; H, 5.12; N, 11.86.
Found: C, 76.32; H, 5.09; N, 11.91%.
References
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O. Tsuge and S. Kanemasa, Advances in heterocyclic chemistry, Vol. 45,
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1b: 1H NMR (500 MHz, DMSO-d6): δ (ppm) 8.07 (s, 1H), 7.90 (d,
2H, J = 8.5 Hz), 7.36 (dd, 1H, J = 1.5 Hz and J = 4.5 Hz), 7.31 (d, 2H,
J = 8.5 Hz), 6.95 (t, 1H, J = 2.0 Hz), 6.20 (dd, 1H, J = 2.0 Hz and
J = 4.5 Hz), 3.98 (s, 3H), 2.44 (s, 3H). Anal. Calcd for C16H14N2O:
C, 76.78; H, 5.64; N, 11.19. Found: C, 76.72; H, 5.69; N, 11.10%.
1c: 1H NMR (500 MHz, DMSO-d6): δ (ppm) 8.07 (s, 1H), 7.99 (dd,
2H, J = 1.5 Hz and J = 7.5 Hz), 7.37 (dd, 1H, J = 1.5 Hz and J = 4.0
Hz), 6.89 (t, 1H, J = 1.5 Hz), 6.71 (d, 2H, J = 7.5 Hz), 6.19 (dd, 1H,
J = 2.5 Hz and J = 4.0 Hz), 3.96 (s, 3H), 3.11 (s, 6H). Anal. Calcd for
C17H17N3O: C, 73.10; H, 6.13; N, 15.04. Found: C, 73.19; H, 6.17; N,
15.08%.
6
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1d: 1H NMR (500 MHz, DMSO-d6): δ (ppm) 8.56 (s, 1H), 8.30 (dd,
1H, J = 1.5 Hz and J = 8.0 Hz), 7.52−7.48 (m, 1H), 7.31 (dd, 1H, J =
1.5 Hz and J = 4.0 Hz), 7.08 (t, 1H, J = 7.5 Hz), 6.97−6.95 (m, 2H),
6.21 (dd, 1H, J = 2.5 Hz and J = 4.0 Hz), 3.98 (s, 3H), 3.89 (s, 3H).