PAPER
A Concise Synthesis of 3-Arylated Di- and Tetrahydro-2H-2-benzazepin-1-ones
1415
Table 2 Physical and Spectroscopic Data of 2-Benzazepine-1,3-diones 4a–e and 2-Benzazepin-1-ones 11a–e, 12a–e Prepared (continued)
Producta
1H NMR (CDCl3–TMS): δ, J (Hz)
13C NMR (CDCl3–TMS): δ
Mp (°C)
oil
12c
0.81 (t, J = 7.3, 3 H, CH3), 1.45–1.63 (m, 2 H, CH2), 2.03– 11.8 (CH3), 23.2 (CH2), 30.3 (CH2), 33.6 (CH2),
2.09 (m, 1 H, CH2), 2.58–2.66 (m, 1 H, CH2), 2.74–2.96 (m, 45.0 (CH2), 56.3 (2 OCH3), 59.9 (OCH3), 60.3
3 H, CH2, NCH2), 3.63–3.68 (m, 1 H, NCH2), 3.82 (s, 6 H, 2 (NCH), 106.0 (2 CH), 127.2 (CH), 128.1 (CH),
128.6 (CH), 130.8 (CH), 132.7 (Cq), 136.6 (Cq),
137.3 (Cq), 144.2 (Cq), 153.2 (2 Cq), 170.9 (C=O)
OCH3), 3.94 (s, 3 H, OCH3), 4.65 (dd, J = 4.7, 12.3, 1 H,
NCH), 6.46 (s, 2 H, Harom), 7.11–7.18 (d, J = 7.2, 1 H, Harom),
7.27–7.38 (m, 2 H, Harom), 7.73 (d, J = 7.4, 1 H, Harom
)
12d
12e
oil
oil
2.07–2.15 (m, 1 H, CH2), 2.48–2.54 (m, 1 H, CH2), 2.73 (s, 3 29.5 (NCH3), 30.6 (CH2), 31.5 (CH2), 55.5
H, NCH3), 2.89–3.12 (m, 2 H, CH2), 3.91 (s, 3 H, OCH3), (NCH), 56.0 (2 OCH3), 113.6 (CH), 115.9 (CH),
3.95 (s, 3 H, OCH3), 4.76 (dd, J = 4.7, 12.5, 1 H, NCH), 6.64 127.4 (2 CH), 128.2 (CH), 128.5 (2 CH), 128.9
(Cq), 133.5 (Cq), 134.4 (Cq), 148.6 (Cq), 153.3
(Cq), 171.3 (C=O)
(s, 1 H, Harom), 7.10–7.16 (m, 2 H, Harom), 7.31–7.40 (m, 3 H,
Harom), 7.59 (s, 1 H, Harom
)
2.08–2.19 (m, 1 H, CH2), 2.51–2.57 (m, 1 H, CH2), 2.80–2.98 30.1 (CH2), 34.2 (CH2), 45.8 (NCH2), 53.5
(m, 2 H, CH2), 3.20 (s, 3 H, OCH3), 3.29 (s, 3 H, OCH3), 3.79 (OCH3), 53.6 (OCH3), 55.9 (OCH3), 56.0
(dd, J = 7.0, 13.0, 1 H, NCH2), 3.85 (s, 6 H, 2 OCH3), 3.87 (s, (OCH3), 56.1 (2 OCH3), 60.5 (NCH), 100.8
6 H, 2 OCH3), 4.52 (dd, J = 4.6, 13.1, 1 H, NCH2), 4.65–4.72 (OCHO), 108.7 (CH), 110.7 (CH), 111.6 (CH),
113.9 (CH), 121.9 (CH), 128.6 (Cq), 130.5 (Cq),
136.1 (Cq), 147.2 (Cq), 148.8 (Cq), 149.5 (Cq),
152.5 (Cq), 171.1 (C=O)
(m, 2 H, OCHO, NCH), 6.61 (s, 1 H, Harom), 6.68–6.85 (m, 3
H, Harom), 7.25 (s, 1 H, Harom
)
a Satisfactory microanalyses obtained: C ± 0.29, H ± 0.25, N ± 0.29.
(4) Ishibashi, H.; Kobayashi, T.; Nakashima, S.; Tamura, O.
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(5) Cross, P. E.; Arrowsmith, J. E. EP 285,323 1988; Chem.
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Acknowledgment
This research was supported by the CNRS and by MENESR. The
authors are grateful to M. Dubois for technical assistance.
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36, 2386. (b) Vogt, B. R. US 3,985,731 1976; Chem. Abstr.
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Synthesis 2012, 44, 1410–1416