10.1002/ejoc.201801021
European Journal of Organic Chemistry
J = 7.3 Hz, 2H), 7.25 – 7.20 (m, 1H), 7.17 – 7.07 (m, 2H), MHz, CDCl3) δ = 8.15 – 8.05 (m, J = 25.8, 7.7 Hz, 2H),
7.04 (d, J = 8.1 Hz, 1H), 4.76 (t, J = 5.6 Hz, 1H), 1.99 –
1.91 (m, 1H), 1.90 – 1.83 (m, 1H), 0.94 (t, J = 7.4 Hz,
3H).13C NMR (151 MHz, CDCl3) δ = 151.97, 149.51,
132.42, 130.93, 128.25, 127.86, 127.45, 126.28, 124.62,
123.04, 115.37, 55.34, 31.74, 9.06.HRMS (ESI-TOF)
m/z = 238.1247 [M + H] +, calcd for C16H16NO:
238.1232
7.41 (t, J = 8.6 Hz, 2H), 7.22 (d, J = 8.3 Hz, 1H), 7.17 –
7.09 (m, 2H), 7.02 (d, J = 7.9 Hz, 1H), 4.81 (q, J = 6.8
Hz, 1H), 1.57 (d, J = 6.9 Hz, 3H).13C NMR (101 MHz,
CDCl3) δ = 150.70, 148.65, 137.08, 133.38, 130.89,
128.79, 128.46, 127.97, 126.01, 124.91, 115.45, 50.03,
25.31.HRMS (ESI-TOF) m/z = 258.0678 [M +H] +, calcd
for C15H13ClNO: 258.0686
2, 4-diphenyl-4H-benzo[e][1,3]oxazine (2m) Yellow
liquid, 42 mg (73 % yield); 1H NMR (400 MHz, CDCl3)
δ = 8.13 (d, J = 7.3 Hz, 2H), 7.47 (d, J = 7.1 Hz, 1H),
7.43 (t, J = 7.4 Hz, 2H), 7.33-7.26 (m, 4H), 7.23 (d, J =
7.5 Hz, 2H), 7.11 (d, J = 8.0 Hz, 1H), 7.06 (t, J = 7.5 Hz,
7-methoxy-4-methyl-2-phenyl-4H-
benzo[e][1,3]oxazine (2s) Yellow liquid, 40 mg (78 %
yield); 1H NMR (600 MHz, CDCl3) δ = 8.07 (d, J = 7.1
Hz, 2H), 7.47 (t, J = 7.2 Hz, 1H), 7.43 (t, J = 7.3 Hz, 2H),
6.98 (d, J = 8.8 Hz, 1H), 6.78 (q, J = 8.8, 2.9 Hz, 1H),
1H), 6.95 (d, J = 7.5 Hz, 1H), 5.85 (s, 1H).13C NMR (101 6.65 (d, J = 2.9 Hz, 1H), 4.81 (q, J = 6.9 Hz, 1H), 3.80 (s,
MHz, CDCl3) δ = 152.08, 148.58, 144.16, 132.23, 131.15, 3H), 1.58 (d, J = 6.9 Hz, 3H).13C NMR (151 MHz,
128.71, 128.25, 127.75, 127.68, 127.45, 127.41, 124.91,
122.73, 121.75, 115.68, 58.80.HRMS (ESI-TOF) m/z =
286.1220 [M + H] +, calcd for C20H16NO: 286.1232
CDCl3) δ = 156.53, 151.83, 142.74, 132.52, 130.87,
128.22, 127.39, 125.45, 116.31, 113.31, 110.66, 55.69,
50.39, 25.35.HRMS (ESI-TOF) m/z = 254.1183 [M +H]
Ethyl 2-phenyl-4H-benzo[e][1,3]oxazine-4-carboxylate +, calcd for C16H16NO2: 254.1181
(2n) Yellow liquid, 29 mg (52 % yield); 1H NMR (600
MHz, CDCl3) δ = 8.13 (d, J = 7.1 Hz, 2H), 7.52 (t, J =
7.3 Hz, 1H), 7.45 (t, J = 7.5 Hz, 2H), 7.32 (t, J = 7.8 Hz,
2H), 7.17 (t, J = 7.5 Hz, 1H), 7.11 (d, J = 8.1 Hz, 1H),
5.54 (s, 1H), 4.22 (q, J = 7.1 Hz, 2H), 1.27 (t, J = 7.1 Hz,
3H).13C NMR (151 MHz, CDCl3) δ = 170.43, 153.92,
148.61, 131.86, 131.47, 129.34, 128.28, 127.82, 126.58,
125.11, 117.25, 116.05, 61.76, 58.20, 14.16.HRMS (ESI-
TOF) m/z = 282.1114 [M + H] +, calcd for C17H16NO3:
282.1130
2-phenyl-4H-benzo[e][1,3]thiazine [19a] (4a)Yellow solid,
36 mg (81 % yield); 1H NMR (600 MHz, CDCl3) δ =
8.00 (d, J = 7.2 Hz, 2H), 7.47 (t, J = 7.3 Hz, 1H), 7.42 (t,
J = 7.4 Hz, 2H), 7.40 – 7.38 (m, 1H), 7.33 – 7.29 (m, 3H),
4.79 (s, 2H).13C NMR (151 MHz, CDCl3) δ = 161.68,
136.98, 131.36, 131.16, 128.55, 127.94, 127.77, 127.56,
127.53, 126.90, 126.65, 56.78.HRMS (ESI-TOF) m/z =
226.0664 [M +H] +, calcd for C14H12NS: 226.0690
4-methyl-2-phenyl-4H-benzo[e][1,3]thiazine (4b)
Yellow solid, 36 mg (76 % yield); 1H NMR (400 MHz,
CDCl3) δ = 7.99 (d, J = 6.7 Hz, 2H), 7.44 (q, J = 11.2, 7.2
Hz, 3H), 7.39 – 7.27 (m, 4H), 4.55 (q, J = 6.9 Hz, 1H),
1.81 (d, J = 6.9 Hz, 3H).13C NMR (151 MHz, CDCl3) δ =
4, 4-dimethyl-2-phenyl-4H-benzo[e][1,3]oxazine (2o)
Yellow liquid, 34 mg (72 % yield); 1H NMR (600 MHz,
CDCl3) δ = 8.09 (d, J = 7.0 Hz, 2H), 7.47 (t, J = 7.2 Hz,
1H), 7.43 (t, J = 7.3 Hz, 2H), 7.26 (s, 1H), 7.23 – 7.22 (m, 159.71, 137.22, 135.17, 131.03, 130.53, 128.52, 127.74,
J = 12.2, 4.7 Hz, 1H), 7.14 (t, J = 7.5 Hz, 1H), 7.05 (d, J
= 8.0 Hz, 1H), 1.60 (s, 6H).13C NMR (151 MHz, CDCl3)
δ = 150.03, 148.14, 132.62, 130.78, 128.62, 128.21,
127.70, 127.48, 125.32, 124.69, 115.45, 52.68,
127.62, 127.05, 126.72, 125.33, 60.06, 18.50.HRMS
(ESI-TOF) m/z = 240.0857 [M +H] +, calcd for C15H14NS:
240.0847
4-ethyl-2-phenyl-4H-benzo[e][1,3]thiazine (4c) Yellow
solid, 36 mg (72 % yield); 1H NMR (600 MHz, CDCl3) δ
= 7.99 (d, J = 7.3 Hz, 2H), 7.49 – 7.45 (m, 1H), 7.43 (t, J
= 7.4 Hz, 2H), 7.36 (d, J = 7.6 Hz, 1H), 7.31 – 7.28 (m, J
= 22.4, 7.5 Hz, 3H), 4.65 (t, J = 7.1 Hz, 1H), 2.07 – 2.03
(m, J = 22.8, 13.7, 7.0 Hz, 2H), 1.13 (t, J = 7.3 Hz,
3H).13C NMR (151 MHz, CDCl3) δ = 158.79, 137.45,
32.54.HRMS (ESI-TOF) m/z = 238.1239 [M + H] +,
calcd for C16H16NO: 238.1232
2, 4, 4-triphenyl-4H-benzo[e][1,3]oxazine [14a] (2p)
Yellow liquid, 55 mg (76 % yield); 1H NMR (600 MHz,
CDCl3) δ = 8.20 (d, J = 7.4 Hz, 2H), 7.48 (t, J = 7.3 Hz,
1H), 7.43 (t, J = 7.5 Hz, 2H), 7.34 – 7.27 (m, 5H), 7.25 –
7.21 (m, 6H), 7.19 (d, J = 8.1 Hz, 1H), 7.10 (t, J = 7.5 Hz, 133.55, 131.01, 130.05, 128.51, 127.69, 127.33, 127.06,
1H), 6.90 (d, J = 6.7 Hz, 1H).13C NMR (101 MHz,
CDCl3) δ = 151.78, 149.03, 147.31, 132.26, 131.07,
129.30, 128.46, 128.34, 128.20, 127.84, 126.83, 125.62,
124.34, 115.70, 65.34.HRMS (ESI-TOF) m/z = 384.1370
[M + Na] +, calcd for C26H19NNaO: 384.1364
4-methyl-2-p-tolyl-4H-benzo[e][1,3]oxazine (2q)
Yellow liquid, 38 mg (80 % yield); 1H NMR (400 MHz,
CDCl3) δ = 7.97 (d, J = 8.1 Hz, 2H), 7.30 – 7.21 (m, 3H),
126.79, 126.63, 66.27, 25.01, 11.31.HRMS (ESI-TOF)
m/z = 254.1017 [M +H] +, calcd for C16H16NS: 254.1003
2, 4-diphenyl-4H-benzo[e][1,3]thiazine (4d) Yellow
solid, 44 mg (73 % yield); 1H NMR (600 MHz, CDCl3) δ
= 8.07 (d, J = 7.2 Hz, 2H), 7.54 (d, J = 7.5 Hz, 2H), 7.47
– 7.42 (m, 5H), 7.38 (d, J = 7.4 Hz, 1H), 7.32 – 7.30 (m,
J = 14.9, 7.7 Hz, 1H), 7.28 (t, J = 7.5 Hz, 1H), 7.22 (d, J
= 7.4 Hz, 1H), 6.85 (d, J = 7.6 Hz, 1H), 5.38 (s, 1H).13C
7.12 (d, J = 4.2 Hz, 2H), 7.03 (d, J = 8.0 Hz, 1H), 4.81 (q, NMR (151 MHz, CDCl3) δ = 160.91, 140.39, 136.96,
J = 6.9 Hz, 1H), 2.40 (s, 3H), 1.57 (d, J = 6.9 Hz, 3H).13C 135.38, 131.21, 130.93, 128.75, 128.56, 128.53, 128.41,
NMR (101 MHz, CDCl3) δ = 151.70, 148.91, 141.17,
129.63, 128.93, 127.84, 127.37, 125.95, 124.83, 124.64,
115.47, 49.96, 25.36, 21.50.HRMS (ESI-TOF) m/z =
238.1210 [M + H] +, calcd for C16H16NO: 238.1232
2-(4-chlorophenyl)-4-methyl-4H-benzo[e][1,3]oxazine
(2r) Yellow liquid, 39 mg (76 % yield);1H NMR (400
127.93, 127.48, 127.27, 127.03, 126.65, 69.01.HRMS
(ESI-TOF) m/z = 302.1021 [M +H] +, calcd for C20H16NS:
302.1003
4, 4-dimethyl-2-phenyl-4H-benzo[e][1,3]thiazine (4e)
Yellow solid, 41 mg (82 % yield); 1H NMR (600 MHz,
CDCl3) δ = 7.95 (d, J = 7.4 Hz, 2H), 7.49 (d, J = 8.0 Hz,
Submitted to the European Journal of Organic Chemistry
5
This article is protected by copyright. All rights reserved.