SHCHEKOTIKHIN et al.
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3.95 m (2H, CH2), 4.98 t (1H, OH, J = 5.0 Hz), 5.09 t
(1H, OH, J = 5.1 Hz), 7.09 s (1H, 3-H), 7.72–7.77 m
(2H, 7-H, 8-H), 8.22–8.27 m (2H, 6-H, 9-H), 11.88 t
(1H, NH, J = 5.4 Hz), 12.40 t (1H, NH, J = 4.7 Hz).
Mass spectrum, m/z (Irel, %): 380 (93) [M]+, 363 (3)
[M – OH]+, 349 (100) [M – CH2OH]+, 320 (9) [M –
NHCH2CH2OH]+, 318 (34) [M – 2CH2OH]+, 304 (11),
290 (20) [M – 2CH2CH2OH]+, 289 (16), 275 (7).
Found, %: C 66.24; H 5.26; N 7.50. C21H20N2O5. Cal-
culated, %: C 66.31; H 5.30; N 7.36. M 380.14.
Compound Xb. Yield 52%, dark blue crystals,
mp 160–161°C, Rf 0.38 (toluene–ethyl acetate, 5:2).
UV spectrum (EtOH), λmax, nm (log ε): 204 (4.4), 275
(4.6), 365 (3.8), 404 (3.7), (520), 567 (4.1), (600).
1H NMR spectrum (CDCl3), δ, ppm: 1.97–2.05 m (8H,
CH2), 2.47 s (3H, CH3), 3.46–3.62 m (8H, CH2), 6.79 s
(1H, 3-H), 7.59–7.63 m (2H, 7-H, 8-H), 8.15–8.18 m
(2H, 6-H, 9-H). Mass spectrum, m/z (Irel, %): 398 (100)
[M – 2H]+, 383 (25), 342 (14), 330 (52) [M – C4H8N]+,
288 (10), 70 (18) [C4H8N]+. Found, %: C 74.87;
H 6.12; N 7.08. C25H24N2O3. Calculated, %: C 74.98;
H 6.04; N 7.00. M 400.18.
Compound XIa. Yield 28%, red–brown crystals,
mp 192–193°C, Rf 0.38 (toluene–ethyl acetate, 5:3).
UV spectrum (EtOH), λmax, nm (log ε): 204 (4.1), 260
Compound XIb. Yield 30%, red–brown crystals,
mp 195–196°C, Rf 0.64 (toluene–ethyl acetate, 5:2).
UV spectrum (EtOH), λmax, nm (logε): 204 (4.4), 261
1
(4.5), 325 (3.5), 518 (3.9), (555). H NMR spectrum
(CDCl3), δ, ppm: 1.12 t (3H, CH3, J = 7.5 Hz), 1.92–
2.03 m (2H, CH2), 2.50 s (3H, CH3), 3.83 t (2H,
CH2OH, J = 5.2 Hz), 4.05 t (2H, NHCH2, J = 5.4 Hz),
4.20 t (2H, OCH2, J = 6.8 Hz), 6.81 d (1H, 3-H, J =
0.8 Hz), 7.64–7.69 m (2H, 7-H, 8-H), 8.18–8.22 m
(2H, 6-H, 9-H). Mass spectrum, m/z (Irel, %): 379 (51)
[M]+, 348 (26) [M – CH2OH]+, 337 (11) [M – C3H6]+,
336 (16) [M – C3H7]+, 319 (7) [M – NHCH2CH2OH]+,
306 (100) [M – C3H6 – CH2OH]+, 304 (9), 43 (61)
[C3H7]+, 42 (15) [C3H6]+. Found, %: C 69.84; H 5.76;
N 3.54. C22H21NO5. Calculated, %: C 69.65; H 5.58;
N 3.69. M 379.14.
1
(4.5), 344 (3.6), (360), 507 (3.8). H NMR spectrum
(CDCl3), δ, ppm: 1.11 t (3H, CH3, J = 7.3 Hz), 1.93–
2.06 m (6H, CH2), 2.50 s (3H, CH3), 3.52 t (4H, CH2,
J = 6.3 Hz), 4.18 t (2H, OCH2, J = 6.9 Hz), 6.80 d (1H,
3-H, J = 0.9 Hz), 7.62–7.68 m (2H, 7-H, 8-H), 8.16–
8.17 m (2H, 6-H, 9-H). Mass spectrum, m/z (Irel, %):
389 (45) [M]+, 346 (100) [M – C3H7]+, 330 (78) [M –
OC3H7]+, 318 (12) [M – C4H8NH]+, 304 (31), 249 (9),
70 (10) [C4H8N]+, 43 (58) [C3H7]+. Found, %: C 73.79;
H 5.87; N 3.62. C24H23NO4. Calculated, %: C 74.02;
H 5.95; N 3.60. M 389.16.
Compound XIIa. Yield 5%, red–brown crystals,
mp 165–166°C, Rf 0.55 (toluene–ethyl acetate, 5:3).
1H NMR spectrum (CDCl3), δ, ppm: 1.11 t (3H, CH3,
J = 7.5 Hz), 1.88–2.01 m (2H, CH2), 2.53 d (3H, CH3,
J = 1.0 Hz), 3.98–4.12 m (6H, CH2), 6.62 s (1H, 3-H),
7.66–7.71 m (2H, 7-H, 8-H), 8.21–8.24 m (2H, 6-H,
9-H). Mass spectrum, m/z (Irel, %): 379 (49) [M]+, 348
(24) [M – CH2OH]+, 337 (9) [M – C3H6]+, 336 (33)
[M – C3H7]+, 320 (6) [M – OC3H7]+, 319 (9) [M –
NHCH2CH2OH]+, 306 (100) [M – C3H6 – CH2OH]+,
304 (11) [M – NHCH2CH2OH – CH3]+, 292 (8) [M –
C3H6 – CH2CH2OH]+, 277 (5) [M – NHCH2CH2OH –
C3H6]+, 43 (61) [C3H7]+. Found, %: C 69.71; H 5.45;
N 3.65. C22H21NO5. Calculated, %: C 69.65; H 5.58;
N 3.69. M 379.14.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 43 No. 11 2007