2-Butyl-4H-chromen-4-one (2j), white solid. 1H NMR (CDCl3,
400 MHz): d 8.19 (dd, J = 8.0 and 1.6 Hz, 1H), 7.62–7.67 (m, 1H),
7.42–7.44 (m, 1H), 7.36–7.40 (m, 1H), 6.18 (s, 1H), 2.63 (t, J =
8.0 Hz, 2H), 1.69–1.77 (m, 2H), 1.39–1.48 (m, 2H), 0.97 (t, J =
8.0 Hz, 3H). 13C NMR (CDCl3, 100 MHz): d 178.5 (C O), 170.0,
156.6, 133.5, 125.8, 125.0, 123.8, 118.0, 109.9 (Ar–C), 34.1, 29.0,
22.2, 13.8. MS (EI) m/z 202 (M+).
Acknowledgements
F. L. acknowledges the National Natural Science Foundation
of China (21002106 and 20625308) and the Chinese Academy
of Science for financial support. H. V. H. thanks the National
University of Singapore for financial support (R-143-000-407-
112).
N-(2-iodophenyl)pivalamide (3f), white solid. 1H NMR (CDCl3,
400 MHz): d 8.12 (d, J = 8.0 Hz, 1H), 7.68 (s, 1H), 7.58 (d, J =
8.0 Hz, 1H), 7.16 (t, J = 8.0 Hz, 1H), 6.65 (t, J = 8.0 Hz, 1H),
1.22 (s, 9H). 13C NMR (CDCl3, 100 MHz): d 176.2 (C O), 138.4,
138.1, 128.9, 125.5, 121.7, 90.2 (Ar–C), 39.8, 27.5. HRMS (ESI)
for [C11H14INNaO] calculated 326.0012, found 326.0009.
2-Methyl-4H-benzo[d][1,3]oxazin-4-one (4a), white solid. 1H
NMR (CDCl3, 400 MHz): d 8.18 (dd, J = 8.0 and 1.2 Hz,
1H), 7.78–7.82 (m, 1H), 7.30–7.55 (m, 2H), 2.48 (s, 3H). 13C
NMR (CDCl3, 100 MHz): d 160.3 (C O), 159.7 (C N), 146.4,
136.6, 128.5, 128.2, 126.4, 116.7 (Ar–C), 21.4. MS (EI) m/z
161 (M+).
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1
2-tert-Butyl-4H-benzo[d][1,3]oxazin-4-one (4b), white solid. H
NMR (CDCl3, 400 MHz): d 8.18 (dd, J = 8.0 and 1.2 Hz, 1H),
7.76–7.80 (m, 1H), 7.58–7.60 (m, 1H), 7.46–7.51 (m, 1H), 1.41 (s,
9H). 13C NMR (CDCl3, 100 MHz): d 168.3 (C O), 160.1 (C N),
146.6, 136.3, 128.3, 128.1, 127.0, 116.9 (Ar–C), 38.0, 27.8. MS (EI)
m/z 203 (M+).
2-Phenyl-4H-benzo[d][1,3]oxazin-4-one (4c), white solid. 1H
NMR (CDCl3, 400 MHz): d 8.31–8.33 (m, 2H), 8.25 (dd, J =
8.0 and 1.2 Hz, 1H), 7.81–7.86 (m, 1H), 7.70 (d, J = 8.0 Hz,
1H), 7.57–7.60 (m, 1H), 7.50–7.54 (m, 3H). 13C NMR (CDCl3,
100 MHz): d 159.7 (C O), 157.3 (C N), 147.1, 136.7, 132.8,
130.4, 128.9, 128.8, 128.5, 128.4, 127.4, 117.2 (Ar–C). MS (EI) m/z
223 (M+).
2-p-Chlorophenyl-4H-benzo[d][1,3]oxazin-4-one (4d), white
solid. 1H NMR (CDCl3, 400 MHz): d 8.23–8.26 (m, 3H),
7.82–7.86 (m, 1H), 7.68 (d, J = 8.0 Hz, 1H), 7.51–7.55 (m, 1H),
7.47–7.50 (m, 2H). 13C NMR (CDCl3, 100 MHz): d 159.4 (C O),
156.4 (C N), 146.9, 139.2, 136.8, 129.7, 129.3, 128.9, 128.8,
128.6, 127.4, 117.1 (Ar–C). MS (EI) m/z 257 (M+).
2-p-Toyl-4H-benzo[d][1,3]oxazin-4-one (4e), white solid. 1H
NMR (CDCl3, 400 MHz): d 8.23 (dd, J = 8.0 and 1.2 Hz, 1H), 8.20
(d, J = 8.0 Hz, 2H), 7.80–7.84 (m, 1H), 7.67 (d, J = 8.0 Hz, 1H),
7.48–7.52 (m, 1H), 7.31 (d, J = 8.0 Hz, 2H), 2.44 (s, 3H). 13C NMR
(CDCl3, 100 MHz): d 159.9 (C O), 157.5 (C N), 147.3, 143.5,
136.7, 129.7, 128.7, 128.5, 128.1, 127.6, 127.2, 117.1 (Ar–C), 21.8.
MS (EI) m/z 223 (M+).
1
Benzoic acid (6a), white solid. H NMR(CDCl3, 400 MHz): d
8.12–8.14 (m, 2H), 7.60–7.65 (m, 1H), 7.49 (t, J = 8.0 Hz, 2H).
13C NMR(CDCl3, 100 MHz): d 172.4 (C O), 134.0, 130.4, 129.5,
128.6 (Ar–C).
2-Methoxybenzoic acid (6b), white solid. 1H NMR (CDCl3,
400 MHz): d 10.95 (s, 1H), 8.15 (dd, J = 8.0 and 1.6 Hz, 1H), 7.56–
7.60 (m, 1H), 7.06–7.14 (m, 2H), 4.07 (s, 3H). 13C NMR (CDCl3,
100 MHz): d 166.0 (C O), 158.2, 135.2, 133.6, 122.1, 117.6, 111.8
(Ar–C), 56.7. HRMS (ESI) for [C8H8NaO3] calculated 175.0366,
found 175.0357.
2-Bromobenzoic acid (6c), white solid. 1H NMR(CDCl3,
400 MHz): d 8.00–8.02 (m, 1H), 7.71–7.74 (m, 1H), 7.38–7.44
(m, 2H). 13C NMR (CDCl3, 100 MHz): d 170.3 (C O), 135.0,
133.7, 132.6, 130.4, 127.5, 122.7 (Ar–C).
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The Royal Society of Chemistry 2011
Dalton Trans., 2011, 40, 7632–7638 | 7637
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