1702
J. Hénin et al.
PAPER
Table 8 1H and 13C NMR Spectral Data of Other Cyclized Products 9,10,11,13–15a (continued)
Prod- 1H NMR (CDCl3/TMS) , J (Hz)
uct
13C NMR (CDCl3/TMS),
14d
7.53–6.78 (m, 20 H, arom. and indol. H), 4.71 (min.)
and 4.69 (maj.) (s, 2 H, CH2Ph), 4.13–3.96 (m, 5 H),
3.73–3.47 (m, 4 H), 3.02 (min.) (t, J = 6.6, 2 H) and
2.93 (maj.) (t, J = 6.8, 2 H) (2 CH2), 2.29–1.02 (m, 25
H)
173.3, 173.2 (CO), 138.0, 137.9, 137.0, 136.2 (quat. of phenyl, C-7a, C-
7’a), 128.6, 128.5, 128.1, 127.3, 127.2, 126.3, 126.2, 126.1, 125.7, 125.5
(CH of phenyl and C-2, C-2’), 127.8, 127.7, 127.5, 127.4 (C-3a, C-3’a),
121.6, 121.3 (C-6, C-6’), 118.8, 118.7, 118.6, 118.4 (C-4, C-4’, C-5, C-
5’), 11.2, 110.6, 110.5 (C-3, C-3’), 109.4, 109.3, 109.2 (C-7, C-7’), 51.8,
51.7 (NCH2Ph), 48.0, 47.9, 47.5, 47.4, 46.2, 46.0, 45.9, 45.8, 45.7 (in-
dol.–CH2CH2 and Na-CH2), 33.5, 33.3, 32.7, 32.6, 30.0, 29.9, 29.4, 29.2,
29.1, 29.0, 28.9, 28.8, 28.5, 26.9, 26.8, 26.6, 25.6, 25.4, 25.3, 25.2, 24.2,
24.0, 23.1, 23.0 [indol.–CH2 and CO(CH2)7]
15
8.81 (min.) and 8.71 (maj.) (s, 1 H, Na-H), 8.44 (maj.)
and 8.29 (min.) (s, 1 H, Na-H), 7.58–6.66 (m, 40 H, in-
dol. and arom. H), 4.68–4.6 (m, 8 H, CH2Ph), 4.22–
4.08 (m, 4 H), 3.9–3.61 (m, 4 H), 3.4 (t, J = 6.8, 1 H),
3.15 (t, J = 6.9, 1 H), 3.08–2.93 (m, 6 H), 2.82 (t,
J = 6.7, 1 H), 2.74 (t, J = 6.7, 1 H), 2.73 (t, J = 7, 1 H),
2.12–1.59 (m, 12 H), 1.12–1.07 (m, 2 H), 1.0–0.93 (m,
2 H), 0.8–0.72 (m, 2 H), 0.66–0.57 (m, 2 H)
(DMSO-d6, 353 K): 172.3, 171.2 (2 CO), 138.2 (quat. of phenyl),
136.2, 136.0 (quat. of phenyl and C-7a), 128.4, 128.1, 127.9, 127.0 (CH
of phenyl), 127.4 (C-3a), 120.8, 120.7 (C-2, C-6), 118.2, 118.1, 117.8
(C-5, C-5', C-4, C-4'), 110.8 (C-3), 111.1, 109.3 (C-7 and C-7'), 47.6,
44.5 (CH2Ph and indol.–CH2CH2), 40.1 (NCH2), 28.7, 25.4, 23.8 [(CH2)2
and indol.–CH2)], 10.8 (CH cyclopropyl), 7.0 (CH2 cyclopropyl)
a Assignments follow the usual indole numbering.
Table 9 1H and 13C NMR Spectral Data for Imines 16c–e and Reduced Compounds 17c–e
8
7
10
9
13
12
N
9
11
14
N
N
8
6
11
10
11
12
13
15
16
5a
7a
10a
N
13
N
15
N
18
(CH2)5
1 to 5
(CH2)7
1 to 7
(CH2)10
1 to 10
12
14
17
16e, 17e
16c, 17c
16d, 17d
Prod- 1H NMR (CDCl3/TMS) , J (Hz)
uct
13C NMR (CDCl3/TMS),
16c
7.6 (d, J = 7.9, 1 H, H-9), 7.34–7.25 (m, 2 H, H-12, H-10), 7.13 (dt,
J = 7.1, 1.5, 1 H, H-11), 4.52 (t, J = 6.5, 2 H, CH2), 3.84 (t, J = 8.2,
2 H, CH2), 2.99 (t, J = 7.1, 2 H, CH2), 2.87 (t, J = 8.5, 2 H, CH2),
1.95–1.85 (m, 4 H, 2 CH2), 1.41–1.32 (m, 2 H, CH2)
161.2 (C-5a), 136.9 (C-12a), 131.3 (C-13a), 124.4 (C-8b),
124.0 (C-11), 119.9, 119.7 (C-9 and C-10), 115.8 (C-8a),
109.6 (C-12), 48.2, 42.9, 37.1, 28.7, 26.1, 22.0, 19.3 (7 x CH2)
16d
7.58 (d, J = 7.9, 1 H, H-11), 7.37 (d, J = 8.3, 1 H, H-14), 7.27 (dt,
J = 7, 1.1, 1 H, H-12), 7.15 (dt, J = 5.4, 0.4, 1 H, H-13), 4.45–4.32
(m, 2 H, CH2), 3.8–3.62 (m, 2 H, CH2), 3.01–2.78 (m, 4 H, 2
CH2), 2.14–2.03 (m, 2 H, CH2), 1.89–1.77 (m, 2 H, CH2), 1.75–
1.64 (m, 2 H, CH2), 1.56–1.46 (m, 4 H, 2 CH2)
162.6 (C-7a), 138.3 (C-14a), 130.5 (C-15a), 124.8 (C-10b),
124.0 (C-13), 119.8 (C-11 and C-12), 119.0 (C-10a) 110.7 (C-
14), 47.5, 42.8, 33.7, 28.8, 25.0, 24.0, 22.1, 21.1, 19.6 (9 x
CH2).
16e
17c
17d
7.55 (d, J = 8.1, 1 H, ArH), 7.29–7.24 (m, 2 H, 2 ArH), 7.10 (dt,
J = 7.1, 1.4, 1 H, ArH), 4.19 (t, J = 8.4, 2 H, CH2), 3.72 (t, J = 8, 2
H, CH2), 2.74 (dd, J = 15, 6.7, 4 H, 2 CH2), 1.92–1.79 (m, 4 H, 2
CH2), 1.52–1.24 (m, 12 H, 6 CH2)
161.0 (C-10a), 138.3 (C-17a), 131.0 (C-18a), 124.5 (C-13b),
124.1 (C-16), 119.8, 119.7 (C-15 and C-14), 118.6 (C-13a),
110.2 (C-17), 47.6, 45.1, 35.8, 27.3, 26.6, 26.3, 24.9, 24.5,
24.4, 24.3, 24.2, 19.6 (12 x CH2)
7.48 (d, J = 7.7, 1 H, H-9), 7.24 (d, J = 8, 1 H, H-12), 7.15 (t, J = 8,
1 H, H-11), 7.06 (t, J = 7.3, 1 H, H-10), 4.2 (dd, J = 14.9, 4.6, H-5a),
3.99–3.83 (m, 2 H, CH2), 3.29–3.14 (m, 2 H, CH2), 2.81–2.68 (m,
2 H, CH2), 2.57 (br s., 1 H, NH), 2.09–0.74 (m, 8 H, 4 CH2)
138.0 (C-12a), 135.3 (C-13a), 126.9 (C-8b), 120.7 (C-11),
118.6 (C-9), 117.9 (C-10), 108.5 (C-12), 105.9 (C-8a), 50.9
(C-5a), 39.7, 39.0, 38.7, 29.0, 23.5, 23.0, 22.4 (7 x CH2).
7.48 (d, J = 7.3, 1 H, H-11), 7.31 (d, J = 8, 1 H, H-14), 7.16 (dt,
J = 7, 1.3, 1 H, H-13), 7.08 (dt, J = 7.5, 1.1, 1 H, H-12), 4.32 (t,
J = 4.7, 1 H, H-7a), 4.16–4.11 (m, 2 H, CH2), 3.38–3.28 (m, 2 H,
CH2), 3.09–2.99 (m, 1 H), 2.79 (t, J = 6.2, 2 H, CH2), 2.41–1.13 (m,
12 H)
136.8, 136.6 (C-14a and C-15a), 127.5 (C-10b), 121.1 (C-13),
118.9 (C-11), 117.9 (C-12), 110.0 (C-14), 109.0 (C-10a), 52.2
(C-7a), 43.2, 40.9, 29.9, 28.8, 24.9, 24.6, 22.5, 20.5, 20.1 (9 x
CH2).
17e
7.46 (d, J = 7.6, 1 H, H-14), 7.24 (d, J = 8, 1 H, H-17), 7.14 (dt,
J = 8, 1, 1 H, H-16), 7.05 (dt, J = 7, 0.6, 1 H, H-15), 4.03–3.98 (m,
2 H, CH2), 3.87–3.77 (m, 1 H, H-10a), 3.14–3.09 (m, 2 H, CH2),
2.73–2.68 (m, 2 H, CH2), 2.3 (br s, 1 H, NH), 1.88–1.25 (m, 18 H,
137.2 (C-17a), 136 (C-18a), 126.8 (C-13b), 120.9 (C-16),
118.6 (C-15), 117.8 (C-14), 108.6 (C-17), 107.5 (C-13a), 48.8
(C-10a), 42.3, 38.4, 30.3, 26.2, 25.8, 24.4, 24.1, 24.06, 24.03,
23.8, 22.9, 22.6 (12 x CH2)
9
CH2)
Synthesis 2001, No. 11, 1693–1703 ISSN 0039-7881 © Thieme Stuttgart · New York