Zhang et al.
Concise Report
1
0.35. H NMR (400 MHz, Chloroform‐d) δ: 8.40—8.27 (m, 2H),
37.0 mg, 0.130 mmol, 65% yield. White solid, Rf (PE/EA, V:V=10:
1)=0.38. 1H NMR (400 MHz, Chloroform‐d) δ: 8.29 (d, J=8.8 Hz,
2H), 8.08 (d, J=6.4 Hz, 2H), 7.64—7.42 (m, 5H), 6.60 (s, 1H); 13C
NMR (101 MHz, Chloroform‐d) δ: 162.3, 161.8, 159.6, 140.0,
134.3, 132.1, 130.0, 129.3, 129.0, 128.5, 127.4, 101.9; HRMS (ESI):
calcd m/z [M+H]+ for [C16H10ClNO2H]+: 284.0473, found: 284.0469.
4‐Phenyl‐2‐(4‐(trifluoromethyl)phenyl)‐6H‐1,3‐oxazin‐6‐one
(2r). 38 mg, 0.120 mmol, 60% yield. Pale yellow solid, Rf (PE/EA, V:
V=10 : 1)=0.55. 1H NMR (400 MHz, Chloroform‐d) δ: 8.48 (d, J=
8.2 Hz, 2H), 8.16—8.06 (m, 2H), 7.80 (dt, J=8.1, 0.8 Hz, 2H),
8.11 (t, J=1.6 Hz, 1H), 7.93 (dt, J=8.0, 1.2 Hz, 1H), 7.64 (t, J=7.4
Hz, 1H), 7.58—7.50 (m, 3H), 7.46 (t, J=7.8 Hz, 1H), 6.58 (s, 1H);
13C NMR (101 MHz, Chloroform‐d) δ: 163.5, 160.5, 159.5, 136.3,
135.2, 133.6, 131.8, 130.2, 129.8, 128.9, 128.8, 127.6, 125.3,
102.5; HRMS (ESI): calcd m/z [M+H]+ for [C16H10ClNO2H]+:
284.0473, found: 284.0469.
4‐(3‐Methoxyphenyl)‐2‐phenyl‐6H‐1,3‐oxazin‐6‐one (2j). 42.4
mg, 0.152 mmol, 76% yield. White solid, Rf (PE/EA, V:V=10:1)=
1
0.40. H NMR (400 MHz, Chloroform‐d) δ: 8.40—8.31 (m, 2H),
7.71—7.59 (m, 3H), 7.53 (dd, J=8.3, 6.9 Hz, 2H), 7.43 (t, J=8.2 Hz, 7.61—7.49 (m, 3H), 6.66 (s, 1H); 13C NMR (101 MHz, Chloroform‐d)
1H), 7.09 (ddd, J=8.3, 2.5, 1.0 Hz, 1H), 6.59 (s, 1H), 3.91 (s, 3H);
13C NMR (101 MHz, Chloroform‐d) δ: 163.1, 161.7, 160.0, 159.9,
135.9, 133.4, 130.0, 130.0, 128.9, 128.8, 119.7, 117.4, 113.0,
102.0, 55.5; HRMS (ESI): calcd m/z [M+H]+ for [C17H13NO3H]+:
280.0968, found: 280.0953.
δ: 161.7, 161.6, 159.3, 134.7 (q, J=32.6 Hz), 134.1, 133.3, 132.2,
129.1, 129.1, 127.4, 125.9 (q, J=3.8 Hz), 123.6 (q, J=271.1 Hz),
102.5; 19F NMR (376 MHz, Chloroform‐d) δ: –63.1; HRMS (ESI):
calcd m/z [M+H]+ for [C17H10F3NO2H]+: 318.0736, found: 318.0730.
4‐(Naphthalen‐2‐yl)‐2‐phenyl‐6H‐1,3‐oxazin‐6‐one (2s). 49.3
mg, 0.164 mmol, 82% yield. White solid, Rf (PE/EA, V:V=10:1)=
0.29. 1H NMR (400 MHz, Chloroform‐d) δ: 8.73 (s, 1H), 8.41 (d, J=
8.1 Hz, 2H), 8.09—7.84 (m, 5H), 7.67—7.51 (m, 4H), 6.72 (s, 1H);
13C NMR (101 MHz, Chloroform‐d) δ: 161.7, 159.9, 135.0, 133.4,
133.0, 131.6, 130.1, 129.3, 128.8, 128.8, 128.8, 128.6, 128.0,
127.8, 126.9, 123.3, 101.9; HRMS (ESI): calcd m/z [M+H]+ for
[C20H13NO2H]+: 300.1019, found: 300.1014.
4‐(2‐Methoxyphenyl)‐2‐phenyl‐6H‐1,3‐oxazin‐6‐one
(2k).
50.2 mg, 0.180 mmol, 90% yield. White solid, Rf (PE/EA, V:V=10:
1)=0.37. 1H NMR (400 MHz, Chloroform‐d) δ: 8.35 (m, 3H),
7.66—7.57 (m, 1H), 7.56—7.44 (m, 3H), 7.22—7.09 (m, 2H), 7.03
(d, J=8.4 Hz, 1H), 3.96 (s, 3H); 13C NMR (101 MHz, Chloroform‐d)
δ: 161.8, 160.6, 159.3, 158.6, 133.1, 132.7, 131.2, 130.3, 128.8,
128.5, 123.2, 120.8, 111.5, 107.0, 55.6; HRMS (ESI): calcd m/z
[M+H]+ for [C17H13NO3H]+: 280.0968, found: 280.0957.
4‐Phenyl‐2‐(thiophen‐2‐yl)‐6H‐1,3‐oxazin‐6‐one (2t).[5c] 30.0
mg, 0.118 mmol, 59% yield. White solid, Rf (PE/EA, V:V=10:1)=
4‐(2‐Chlorophenyl)‐2‐phenyl‐6H‐1,3‐oxazin‐6‐one (2l).[5c] 33
mg, 0.116 mmol, 58% yield. White solid, Rf (PE/EA, V:V=10:1)=
1
0.29. H NMR (400 MHz, Chloroform‐d) δ: 8.07—7.98 (m, 3H),
1
0.36. H NMR (400 MHz, Chloroform‐d) δ: 8.32—8.26 (m, 2H),
7.66 (dd, J=5.2, 1.2 Hz, 1H), 7.57—7.45 (m, 3H), 7.18 (dd, J=4.8,
7.80—7.75 (m, 1H), 7.62—7.56 (m, 1H), 7.53—7.46 (m, 3H),
4.0 Hz, 1H), 6.51 (s, 1H); 13C NMR (101 MHz, Chloroform‐d) δ: 162.2,
7.42—7.38 (m, 2H), 6.64 (s, 1H); 13C NMR (101 MHz, Chloroform‐d) 159.7, 159.4, 134.2, 134.2, 133.6, 132.8, 131.9, 128.9, 128.6, 127.3,
δ: 163.2, 161.4, 159.2, 134.6, 133.4, 132.6, 131.4, 130.9, 130.9,
129.8, 128.8, 128.7, 127.1, 108.2; HRMS (ESI): calcd m/z [M+H]+
for [C16H10ClNO2H]+: 284.0473, found: 284.0473.
100.8; HRMS (ESI): calcd m/z [M+H]+ for [C14H9SNO2H]+: 256.0427,
found: 256.0427.
4‐Cyclohexyl‐2‐phenyl‐6H‐1,3‐oxazin‐6‐one (2u).[12] 40.0 mg,
4‐(3,4‐Dimethoxyphenyl)‐2‐phenyl‐6H‐1,3‐oxazin‐6‐one (2m). 0.157 mmol, 78% yield. White solid, Rf (PE/EA, V:V=10:1)=0.46.
50.1 mg, 0.162 mmol, 81% yield. Pale yellow solid, Rf (PE/EA, V:V
=10 : 1)=0.43. H NMR (400 MHz, Chloroform‐d) δ: 8.34 (d, J=
1H NMR (400 MHz, Chloroform‐d) δ: 8.25 (d, J=7.6 Hz, 2H), 7.53
(m, 3H), 5.99 (s, 1H), 2.54—2.35 (m, 1H), 1.98 (m, 2H), 1.88 (m,
2H), 1.77 (m, 1H), 1.42 (m, 4H), 1.27 (m, 1H); 13C NMR (101 MHz,
Chloroform‐d) δ: 173.6, 162.9, 159.9, 133.1, 130.0, 128.7, 128.5,
103.4, 45.0, 30.6, 25.9, 25.8; HRMS (ESI): calcd m/z [M+H]+ for
[C16H17NO2H]+: 256.1332, found: 256.1332.
1
7.4 Hz, 2H), 7.76 (dd, J=8.5, 1.9 Hz, 1H), 7.66—7.58 (m, 2H), 7.53
(t, J=7.6 Hz, 2H), 6.99 (d, J=8.5 Hz, 1H), 6.50 (s, 1H), 4.00 (s, 3H),
3.97 (s, 3H); 13C NMR (101 MHz, Chloroform‐d) δ: 162.9, 161.4,
160.1, 152.5, 149.2, 133.3, 130.1, 128.8, 128.7, 127.0, 121.3,
111.0, 109.8, 99.9, 56.1, 56.0; HRMS (ESI): calcd m/z [M+H]+ for
[C18H15NO4H]+: 310.1074, found: 310.1085.
4‐Isopropyl‐2‐phenyl‐6H‐1,3‐oxazin‐6‐one (2v).[12] 38 mg,
0.176 mmol, 88% yield. White solid, Rf (PE/EA, V:V=10:1)=0.28.
1H NMR (400 MHz, Chloroform‐d) δ: 8.30—8.21 (m, 2H), 7.58 (t,
J=7.6 Hz, 1H), 7.49 (t, J=7.6 Hz, 2H), 6.02 (s, 1H), 2.77 (m , 1H),
1.28 (d, J=6.8 Hz, 6H); 13C NMR (101 MHz, Chloroform‐d) δ: 174.6,
163.0, 159.9, 133.2, 130.0, 128.8, 128.6, 103.2, 35.3, 20.3; HRMS
(ESI): calcd m/z [M+H]+ for [C13H13NO2H]+: 216.1019, found:
216.1007.
4‐(3,4‐Dimethylphenyl)‐2‐phenyl‐6H‐1,3‐oxazin‐6‐one (2n).
44.3 mg, 0.160 mmol, 80% yield. Pale yellow solid Rf (PE/EA, V:V
1
=10 : 1)=0.40. H NMR (400 MHz, Chloroform‐d) δ: 8.42—8.32
(m, 2H), 7.91—7.81 (m, 2H), 7.66—7.59 (m, 1H), 7.58—7.50 (m,
2H), 7.28 (d, J=8.0 Hz, 1H), 6.57 (s, 1H), 2.38 (s, 3H), 2.35 (s, 3H);
13C NMR (101 MHz, Chloroform‐d) δ: 162.9, 162.0, 160.1, 141.4,
137.3, 133.3, 132.0, 130.3, 130.2, 128.8, 128.7, 128.4, 125.0,
100.8, 20.0, 20.0; HRMS (ESI): calcd m/z [M+H]+ for [C18H15NO2H]+:
278.1176, found: 278.1173.
4‐Cyclopropyl‐2‐phenyl‐6H‐1,3‐oxazin‐6‐one (2w).[12] 29.8 mg,
0.140 mmol, 70% yield. White solid, Rf (PE/EA, V:V=10:1)=0.45.
1H NMR (400 MHz, Chloroform‐d) δ: 8.16 (d, J=7.2 Hz, 2H), 7.55
(t, J=7.2 Hz, 1H), 7.45 (t, J=7.6 Hz, 2H), 6.07 (s, 1H), 1.73 (m, 1H),
1.16 (m, 2H), 0.96 (m, 2H); 13C NMR (101 MHz, Chloroform‐d) δ:
170.9, 163.5, 158.9, 133.2, 129.9, 128.7, 128.5, 102.8, 16.8, 9.4;
HRMS (ESI): calcd m/z [M+H]+ for [C13H11NO2H]+: 214.0863, found:
2‐(4‐Methoxyphenyl)‐4‐phenyl‐6H‐1,3‐oxazin‐6‐one (2o).[5c]
50.6 mg, 0.182 mmol, 91% yield. Pale yellow solid, Rf (PE/EA, V:V
1
=10 : 1)=0.33. H NMR (400 MHz, Chloroform‐d) δ: 8.38—8.27
(m, 2H), 8.14—8.04 (m, 2H), 7.59—7.47 (m, 3H), 7.06—6.98 (m,
2H), 6.54 (s, 1H), 3.91 (s, 3H); 13C NMR (101 MHz, Chloroform‐d) δ: 214.0855.
163.9, 163.2, 162.2, 160.3, 134.7, 131.8, 130.9, 128.9, 127.4,
122.4, 114.3, 100.8, 55.6; HRMS (ESI): calcd m/z [M+H]+ for
[C17H13NO3H]+: 280.0968, found: 280.0965.
4‐(tert‐Butyl)‐2‐phenyl‐6H‐1,3‐oxazin‐6‐one (2x). 16.0 mg,
0.070 mmol, 35% yield. White solid, Rf (PE/EA, V:V=10:1)=0.65.
1H NMR (400 MHz, Chloroform‐d) δ: 8.19 (d, J=7.6 Hz, 2H), 7.51
(t, J=7.6 Hz, 1H), 7.42 (t, J=7.6 Hz, 2H), 6.04 (s, 1H), 1.24 (s, 9H);
13C NMR (101 MHz, Chloroform‐d) δ: 175.6, 161.3, 159.2, 132.0,
129.1, 127.7, 127.5, 101.1, 36.3, 26.9; HRMS (ESI): calcd m/z
[M+H]+ for [C14H15NO2H]+: 230.1176, found: 230.1169.
4‐Phenyl‐2‐(p‐tolyl)‐6H‐1,3‐oxazin‐6‐one (2p).[5c] 40.5 mg,
0.154 mmol, 77% yield. Pale yellow solid, Rf (PE/EA, V : V=10 :1)
1
=0.33. H NMR (400 MHz, Chloroform‐d) δ: 8.26 (d, J=8.4 Hz,
2H), 8.15—8.07 (m, 2H), 7.58—7.50 (m, 3H), 7.34 (d, J=8.0 Hz,
2H), 6.59 (s, 1H), 2.46 (s, 3H); 13C NMR (101 MHz, Chloroform‐d) δ:
163.4, 162.1, 160.1, 144.4, 134.6, 131.9, 129.6, 128.9, 128.8,
127.4, 127.3, 101.4, 21.8; HRMS (ESI): calcd m/z [M+H]+ for
[C17H13NO2H]: 264.1019, found: 264.1014.
2‐Methyl‐4‐phenyl‐6H‐1,3‐oxazin‐6‐one (2y).[5c] 29.9 mg,
0.160 mmol, 80% yield. Pale yellow solid, Rf (PE/EA, V : V=10 :1)
1
=0.60. H NMR (400 MHz, Chloroform‐d) δ: 7.97 (d, J=6.8 Hz,
2H), 7.51 (m, 3H), 6.53 (s, 1H), 2.51 (s, 3H); 13C NMR (101 MHz,
2‐(4‐Chlorophenyl)‐4‐phenyl‐6H‐1,3‐oxazin‐6‐one
(2q).[5c]
Chloroform‐d) δ: 166.9, 161.6, 160.2, 134.2, 131.9, 129.0, 127.3,
434
© 2018 SIOC, CAS, Shanghai, & WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2018, 36, 430-436