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Organic & Biomolecular Chemistry
Page 8 of 9
DOI: 10.1039/C8OB01496E
ARTICLE
Journal Name
1
White solid (77% yield), m.p. 96 - 97°C; H NMR (400 MHz, CDCl3) δ 7.88 (d, 127.8, 127.4, 124.9, 124.2, 122.3, 117.8, 113.6, 110.0, 102.0, 101.5, 79.7,
+
1H, J = 8.8 Hz), 7.77 (d, 1H, J = 8 Hz), 7.51 (d, 1H, J = 8 Hz),7.43-7.26 (m, 70.5. HRMS (ESI) calcd. for C30H21O4 [M+H]+ 445.1440; found 445.1434.
11H), 7.20 – 7.15 (m, 1H), 7.14 – 7.08 (m, 1H); 13C NMR (100 MHz, CDCl3) δ
159.3, 159.1, 143.5, 141.5, 132.0, 131.9, 131.1, 131.0, 130.4, 129.3, 129.2, 4-(4-chlorophenoxy)-3-(2-phenylethynyl)-2H-chromen-2-one (5f)
128.7, 128.1, 127.45, 127.40, 127.0, 125.5, 124.97, 124.92, 124.5, 121.0,
120.5. HRMS (ESI) calcd. for C24H17O+ [M+H]+ 321.1274; found 321.1279.
White crystalline solid (75% yield), m. p. 144-146oC; 1H NMR (400 MHz,
CDCl3) δ 7.89 (dd, 1H, J1=8.0 Hz, J2=1.4 Hz), 7.68 – 7.60 (m, 1H), 7.43 (d, 1H, J
= 8.0 Hz), 7.38 – 7.26 (m, 6H), 7.15 – 7.06 (m, 4H); 13C NMR (100 MHz, CDCl3)
δ 162.8, 160.8, 153.6, 152.1, 133.0, 131.4, 129.8, 129.5, 128.7, 128.0, 124.6,
12-Phenyl benzo[b]naphth[2,1-f]oxepin (3t)
Gummy liquid (79% yield); 8.74 (d, 1H, J = 8.4 Hz), 7.83 (d, 1H, J = 8.0 Hz),
7.67 (t, 1H, J = 7.6 Hz), 7.59-7.47 (m, 4H), 7.46-7.7.34 (m, 6H), 7.20-7.16 (m,
2H), 7.07 (d, 1H, J = 8.8 Hz); 13C NMR (100 MHz, CDCl3) δ 157.6, 153.4, 142.7,
142.3, 134.9, 131.2, 129.7, 129.5, 128.9, 128.7, 128.4, 127.8, 127.6, 127.5,
123.4, 121.9, 119.5, 116.7, 116.2, 103.4, 98.8, 79.4. HRMS (ESI) calcd. for
+
C
23H14ClO3 [M+H]+ 373.0631; found 373.0626.
127.3, 126.8, 126.7, 126.6, 124.9, 123.8, 122.8, 121.1. HRMS (ESI) calcd. for 8-phenyl-6H-benzo[6,7]oxepino[3,2-c]chromen-6-one (6a)
24H17O+ [M+H]+ 321.1274; found 321.1278.
C
Pale yellow crystal (88% yield), m. p. 130-132oC; 1H NMR (400 MHz, CDCl3) δ
7.68 – 7.58 (m, 2H), 7.46 (d, 1H, J = 8.4 Hz), 7.33 – 7.17 (m, 6H), 7.16 – 7.06
(m, 3H), 6.80 – 6.76 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 160.3, 160.0,
155.2, 153.2, 135.1, 134.5, 133.1, 129.4, 128.4, 128.0, 127.9, 127.8, 124.8,
4-phenoxy-3-(phenylethynyl)-2H-chromen-2-one (5a)
White crystalline solid (83% yield), m. p. 84-86oC; H NMR (400 MHz, CDCl3)
1
δ 7.90 (s, 1H), 7.67-7.59 (m, 1H), 7.46 - 7.31 (m, 4H), 7.29-7.18 (m, 4H), 7.20- 124.6, 124.3, 124.2, 121.9, 117.2, 116.9, 116.0, 112.6. HRMS (ESI) calcd. for
7.13 (m, 2H), 7.11 - 7.05 (m, 2H) ; 13C NMR (100 MHz, CDCl3) δ 163.3, 161.1,
+
C23H15O3 [M+H]+ 339.1021; found 339.1017.
155.2, 152.2, 132.9, 131.5, 129.6, 128.5, 127.8, 124.5, 124.3, 123.6, 122.1,
+
117.9, 116.7, 116.5, 103.0, 99.1, 79.6. HRMS (ESI) calcd. for C23H15O3
[M+H]+ 339.1021; found 339.1015.
4-methyl-8-phenyl-6H-benzo[6,7]oxepino[3,2-c]chromen-6-one (6b)
Pale yellow crystal (86% yield), m. p. 128-130oC; 1H NMR (400 MHz, CDCl3) δ
7.48 (t, 2H, J = 6.9 Hz), 7.25 – 7.19 (m, 4H), 7.16 – 7.04 (m, 4H), 6.81 (s, 1H),
6.77 (d, 2H, J = 7.7 Hz), 2.55 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 160.4,
160.3, 155.4, 151.6, 135.1, 134.5, 134.4, 129.3, 129.1, 128.7, 128.4, 127.9,
127.8, 126.4, 124.0, 123.9, 122.4, 122.1, 117.1, 115.8, 112.6, 15.6. HRMS
8-methyl-4-phenoxy-3-(phenylethynyl)-2H-chromen-2-one (5b)
White crystalline solid (82% yield), m. p. 128-130oC; 1H NMR (400 MHz,
CDCl3) δ 7.74 (d, 1H, J = 8.0 Hz), 7.47 (d, 1H, J = 7.3 Hz), 7.43-7.35 (m, 2H),
7.28 – 7.12 (m, 7H), 7.10 (dd, 2H, J1=8.1 Hz, J2=1.4 Hz), 2.54 (s, 3H); 13C NMR
(100 MHz, CDCl3) δ 163.7, 161.1, 155.4, 150.6, 134.3, 131.6, 129.6, 128.5,
127.8, 126.2, 124.1, 124.0, 122.2, 121.3, 117.7, 116.3, 102.8, 99.1, 79.8,
+
(ESI) calcd. for C24H17O3 [M+H]+ 353.1178; found 353.1171.
3-methyl-8-phenyl-6H-benzo[6,7]oxepino[3,2-c]chromen-6-one (6c)
15.5. HRMS (ESI) calcd. for C24H17O3 [M+H]+ 353.1178; found 353.1172.
+
Pale yellow crystal (83% yield), m. p. 158-160oC; 1H NMR (400 MHz, CDCl3) δ
7.50 (d, 1H, J = 8.1 Hz), 7.29-7.18 (m, 6H), 7.14-7.02 (m, 4H), 6.82 – 6.74 (m,
3H), 2.49 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 160.6, 160.3, 155.4, 153.4,
144.8, 135.0, 134.6, 129.4, 128.4, 127.9, 127.8, 127.7, 125.6, 124.5, 124.1,
7-methyl-4-phenoxy-3-(phenylethynyl)-2H-chromen-2-one (5c)
1
White crystalline solid (79% yield), m. p. 94-96oC; H NMR (400 MHz, CDCl3)
123.8, 122.2, 117.1, 117.0, 116.7, 113.4, 21.7. HRMS (ESI) calcd. for
24H17O3 [M+H]+ 353.1178; found 353.1172.
+
δ 7.77 (d, 2H, J = 6.9 Hz), 7.46 (d, 1H, J = 6.7 Hz), 7.39-7.35 (m, 3H), 7.27 –
7.02 (m, 13H), 2.69 (s, 1H), 2.50 (s, 3H). ; 13C NMR (100 MHz, CDCl3) δ13C
NMR (101 MHz, CDCl3) δ 163.5, 162.2, 155.3, 154.7, 153.7, 152.3, 144.5,
136.9, 132.2, 131.5, 131.5, 129.7, 129.6, 128.6, 128.4, 128.2, 127.8, 127.8,
125.8, 124.2, 123.7, 123.3, 122.3, 117.8, 116.8, 116.8, 115.2, 114.0, 105.0,
C
2-methyl-8-phenyl-6H-benzo[6,7]oxepino[3,2-c]chromen-6-one (6d)
Pale yellow crystal (87% yield) , m. p. 120-122oC; 1H NMR (400 MHz, CDCl3) δ
7.44 (dd, 2H, J1=11.6 Hz, J2=3.0 Hz), 7.35 (d, 1H, J = 8.4 Hz), 7.25 – 7.21 (m,
4H), 7.16 – 7.05 (m, 3H), 6.79 (d, 2H, J = 7.8 Hz), 6.75 (s, 1H), 2.35 (s, 3H); 13
C
102.8, 102.5, 98.0, 79.8, 77.2, 76.9, 76.6, 22.8, 21.7. HRMS (ESI) calcd. for
+
C
24H17O3 [M+H]+ 353.1178; found 353.1170.
NMR (100 MHz, CDCl3) δ 160.5, 160.0, 155.2, 151.4, 135.1, 134.5, 134.3,
130.9, 129.3, 128.7, 128.4, 128.0, 127.8, 124.3, 124.2, 122.1, 117.2, 116.6,
+
116.4, 115.8, 112.2, 20.7. HRMS (ESI) calcd. for C24H17O3 [M+H]+ 353.1178;
6-methyl-4-phenoxy-3-(phenylethynyl)-2H-chromen-2-one (5d)
found 353.1173.
White crystalline solid (80% yield), m. p. 102-104oC; 1H NMR (400 MHz,
CDCl3) δ 7.69 (s, 1H), 7.45 – 7.36 (m, 3H), 7.33 – 7.19 (m, 5H), 7.16 (d, 2H, J =
7.9 Hz), 7.07 (d, 2H, J = 6.8 Hz), 2.43 (s, 3H); 13C NMR (100 MHz, CDCl3) δ
163.3, 161.2, 155.2, 150.4, 134.4, 134.0, 131.5, 129.6, 128.5, 127.8, 124.3,
123.2, 122.2, 117.8, 116.4, 116.2, 103.0, 99.0, 79.8, 20.8. HRMS (ESI) calcd.
3-(benzyloxy)-8-phenyl-6H-benzo[6,7]oxepino[3,2-c]chromen-6-one (6e)
Pale yellow powder (90% yield), m. p. 128-130oC; 1H NMR (400 MHz, CDCl3)
δ 7.52 (d, 1H, J = 8.9 Hz), 7.48 – 7.42 (m, 4H), 7.25 – 7.18 (m, 5H), 7.13 – 7.04
(m, 3H), 6.98 (d, 1H, J = 2.4 Hz), 6.87 (dd, 1H, J1 = 8.9 Hz, J2 = 2.4 Hz), 6.83-
6.74 (m, 3H), 5.17 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 162.8, 160.4, 159.4,
155.4, 155.1, 135.4, 134.9, 134.6, 133.3, 129.7, 129.3, 128.7, 128.4, 128.3,
127.8, 127.8, 127.4, 126.0, 124.0, 122.4, 117.1, 113.4, 112.6, 109.3, 101.6,
+
for C24H17O3 [M+H]+ 353.1178; found 353.1172.
7-(benzyloxy)-4-phenoxy-3-(phenylethynyl)-2H-chromen-2-one (5e)
White crystalline solid (70% yield), m. p. 138-140oC; 1H NMR (400 MHz,
CDCl3) δ 7.80 (d, 1H, J = 8.5 Hz), 7.50 – 7.35 (m, 7H), 7.27 – 7.11 (m, 6H), 7.09
– 7.04 (m, 2H), 7.01 – 6.95 (m, 2H), 5.19 (s, 2H). ; 13C NMR (100 MHz, CDCl3)
δ 163.7, 162.8, 161.7, 155.2, 154.1, 135.4, 131.4, 129.6, 128.7, 128.3, 128.3,
70.5. HRMS (ESI) calcd. for C30H21O4 [M+H]+ 445.1440; found 445.1435.
+
8 | J. Name., 2012, 00, 1-3
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