JOURNAL OF CHEMICAL RESEARCH 2012 401
1H), 7.35 (t, J = 7.1 Hz, 1H), 7.42–7.46 (q, 1H), 7.56 (d, J = 8.5 Hz,
1H), 7.67 (d, J = 8.8 Hz, 1H), 7.78 (d, J = 7.8 Hz, 1H). 13C NMR
(100 MHz, CDCl3): δ 25.3, 26.1, 29.8, 50.1, 82.2, 115.0, 120.6, 122.1,
124.7, 125.2, 127.7, 128.7, 129.1, 129.7, 130.0, 132.4, 144.0, 150.6,
153.7. HRMS (ESI, m/z): Calcd for C24H27NO (M+H+) 345.2093;
found: 345.2095.
Received 6 April 2012; accepted 16 April 2012
Paper 1201217 doi: 10.3184/174751912X13371662613770
Published online: 26 June 2012
References
22-(1H-Naphtho[1,2-e][1,3]oxazin-2(3H)-yl)phenol (4m): Yield;
1
2
3
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86%; white solid; m.p. 143-145 °C. H NMR (400 MHz, CDCl3):
δ 4.68 (s, 2H), 5.09 (s, 2H), 6.65 (s, 1H), 6.70–6.74 (m, 1H), 6.99 (dd,
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7.80 (d, J = 8.0 Hz, 1H). 13C NMR (100 MHz, CDCl3): δ 49.3, 80.8,
114.8, 118.7, 120.4, 120.9, 123.9, 124.4, 126.8, 127.4, 128.5, 128.7,
129.1, 131.0, 136.1, 151.3. HRMS (ESI, m/z): Calcd for C18H15NO2
(M+H+) 277.1103; found: 277.1103.
4
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1
oxazine (4n): Yield; 92%; white solid; m.p. 255–257 °C. H NMR
(400 MHz, CDCl3): δ 2.28 (s, 3H), 5.21(s, 2H), 5.67 (s, 2H), 6.57
(d, J = 5.1 Hz, 1H), 6.75 (s, 1H), 7.06 (d, J = 8.7 Hz, 1H), 7.37 (t,
J = 7.3 Hz, 1H), 7.50–7.54 (m, 1H), 7.60 (d, J = 8.7 Hz, 1H), 7.78 (t,
J = 9.1 Hz, 2H), 8.11 (d, J = 5.1 Hz, 1H). 13C NMR (100 MHz, CDCl3):
δ 21.4, 44.4, 75.2, 108.6, 113.0, 116.5, 118.8, 121.1, 123.7, 126.7,
128.2, 128.6, 129.0, 131.3, 147.8, 149.0, 152.3, 157.9. HRMS (ESI,
m/z): Calcd for C18H16N2O (M+H+) 276.1344; found: 276.1264.
2-(9H-Fluoren-7-yl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine
(4o): Yield; 91%; pale yellow solid; m.p. 164–166 °C 1H NMR
(400 MHz, CDCl3): δ 3.81(s, 2H), 5.00(s, 2H), 5.47 (s, 2H), 7.06 (d,
J = 9.1 Hz, 1H), 7.15-7.22 (m, 2H), 7.29–7.39 (m, 3H), 7.46 (d, J =
7.3 Hz, 1H), 7.52 (t, J = 7.6 Hz, 1H), 7.64 (dd, J = 5.1, 13.1 Hz, 3H),
7.72 (d, J = 8.4 Hz, 1H), 7.78 (d, J = 8.4 Hz, 1H). 13C NMR (100 MHz,
CDCl3): δ 37.8, 48.5, 80.4, 112.1, 115.4, 117.7, 119.1, 120.9, 123.6,
124.8, 126.6, 128.2, 131.1, 135.2, 141.5, 143.1, 144.6, 148.4, 150.2,
152.4. HRMS (ESI, m/z): Calcd for C25H19NO (M+H+) 349.1467;
found: 349.1469.
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This research work was supported by the second stage of BK21
Program.