BURMISTROV et al.
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1.28 q (2Н, endo-CH2, J 8.3 Hz), 1.40 q (2Н, exo-CH2,
J 8.4 Hz), 1.47–1.80 m (14H, Ad), 1.78–1.84 m (1H,
endo-CH–CH–NH), 2.02–2.08 m (1H, exo-CH–CH–
NH), 2.57 s (1H, endo-CH–СH2–CH–NH), 2.75 s (1H,
exo-CH–СH2–CH–NH), 2.79 s (1H, endo-CH–СH2–
CH–NH), 2.84 s (1H, exo-CH–СH2–CH–NH), 3.39–
3.44 m (1H, endo-CH–NH), 3.65 t (1H, Ad, J 10.4 Hz),
4.12–4.18 m (1H, exo-CH–NH), 5.41 d (1H, endo-NH,
J 8.4 Hz), 5.96 d (1H, exo-NH, J 8.4 Hz), 5.98 q (1H,
endo-CH=CH–CH–CH–NH, J 2.8 Hz), 6.03 d (1H,
NH–Ad, J 8.5 Hz), 6.04 q (1H, exo-CH=CH–CH–CH–
NH, J 2.8 Hz), 6.11 q (1H, endo-CH=CH–CH–CH–
NH, J 2.8 Hz), 6.32 q (1H, exo-CH=CH–CH–CH–NH,
J 2.9 Hz). 13C NMR spectrum (DMSO-d6), δ, ppm:
26.81 d (Ad, J 12.5 Hz), 31.23 t (Ad, J 7.5 Hz), 32.37
(Ad), 34.53 (endo-CH2–CH–NH), 35.33 (exo-CH2–
CH–NH), 36.96 d (Ad, J 7.5 Hz), 37.28 (Ad), 40.33
(endo-CH–CH2–CH–NH), 42.06 (exo-CH–CH2–CH–
NH), 45.62 (endo-CH–NH), 46.09 (exo-CH–NH),
48.02 (endo- + exo-CH2bridgehead), 48.88 (endo-CH–CH–
NH), 49.48 (exo-CH–CH–NH), 52.68 d (NH–CH Ad,
J 5.0 Hz), 132.20 (endo-CH=CH), 134.85 (endo-
CH=CH), 138.31 (exo-CH=CH), 138.70 (exo-
CH=CH), 157.07 d [NH–C(O)–NH, J 3.7 Hz]. Mass
spectrum, m/z (Irel, %): 286 (28.4) [М]+, 221 (84.1)
[М – cyclopentene]+, 135 (11.0) [Ad]+, 109 (9.5) [M –
AdNCO]+, 79 (8.4), 66 (9.6), 43 (100). Found, %: С
75.52; Н 9.10; N 9.81. C18H26N2O. Calculated, %: С
75.48; Н 9.15; N 9.78. М 286.41.
6.04 q (1H, exo-CH=CH–CH–CH–NH, J 3.1 Hz), 6.11
q (1H, endo-CH=CH–CH–CH–NH, J 2.8 Hz), 6.32 q
(1H, exo-CH=CH–CH–CH–NH, J 3.0 Hz). 13C NMR
spectrum (DMSO-d6), δ, ppm: 27.77 (Ad), 33.42 d (Ad,
J 8.8 Hz), 34.41 (endo-CH2–CH–NH), 35.21 (exo-CH2–
CH–NH), 36.69 (Ad), 39.82 (NH–C Ad), 40.34 (endo-
CH–CH2–CH–NH), 42.06 (exo-CH–CH2–CH–NH),
45.57 (endo-CH–NH), 46.03 (exo-CH–NH), 47.99
(endo- + exo-CH2bridgehead), 49.09 (endo-CH–CH–NH),
49.66 (exo-CH–CH–NH), 51.06 (NH–CH2–Ad), 132.20
(endo-CH=CH), 134.85 (endo-CH=CH), 138.31 (exo-
CH=CH), 138.70 (exo-CH=CH), 157.07 d [NH–C(O)–
NH, J 3.7 Hz]. Mass spectrum, m/z (Irel, %): 300 (16.3)
[М]+, 235 (95.9) [М – cyclopentene]+, 149 (5.4) [Ad–
CH2]+, 135 (19.3) [Ad]+), 93 (8.1), 79 (8.6), 66 (10.8),
43 (100). Found, %: С 76.00; Н 9.35; N 9.36.
C19H28N2O. Calculated, %: С 75.96; Н 9.39; N 9.32. М
300.44.
N-{4-[(Bicyclo[2.2.1]hept-5-en-2-yl)carbamo-
ylamino]butyl}-N'-(bicyclo[2.2.1]hept-5-en-2-yl)-
urea (5a) was prepared similarly to compound 4a from
0.3 g (2.22 mmol) of isocyanate 2b, 0.1 g (1.13 mmol)
of 1,4-diaminobutane, and 0.22 g (2.15 mmol, 0.3 mL)
of TEA in 5 mL of anhydrous DMF. Yield 0.34 g
(86%), mp 248–249°C. 1Н NMR spectrum (DMSO-d6),
δ, ppm: 0.55 d.t (2H, endo-2CH–СH2–CH–NH, J1
11.8 Hz, J2 3.1 Hz), 1.12 d.t (2H, exo-2CH–СH2–CH–
NH, J1 11.9 Hz, J2 3.2 Hz), 1.28 q (4Н, endo-2CH2, J
8.5 Hz), 1.31–1.37 m (4H, 2CH2–CH2–NH), 1.41 q
(4Н, exo-2CH2, J 8.7 Hz), 1.46–1.52 m (2H, endo-
2CH–CH–NH), 2.01–2.07 m (2H, exo-2CH–CH–NH),
2.59 s (2H, endo-2CH–СH2–CH–NH), 2.74 s (2H, exo-
2CH–СH2–CH–NH), 2.77 s (2H, endo-2CH–СH2–
CH–NH), 2.86 s (2H, exo-2CH–СH2–CH–NH), 2.92–
3.01 m (4H, 2CH2–CH2–NH), 3.38–3.43 m (2H, endo-
2CH–NH), 4.10–4.17 m (21H, exo-2CH–NH), 5.09 t
(2H, endo-2NH, J 7.0 Hz), 5.53 s (2H, endo-2NH–СH2),
5.62 s (2H, exo-2NH–СH2), 5.77 t (2H, exo-2NH, J
7.0 Hz), 5.95 q (2H, endo-2CH=CH–CH–CH–NH, J
3.0 Hz), 6.03 q (2H, exo-2CH=CH–CH–CH–NH, J
3.0 Hz), 6.10 q (2H, endo-2CH=CH–CH–CH–NH, J
3.0 Hz), 6.31 q (2H, exo-2CH=CH–CH–CH–NH, J
3.0 Hz). 13C NMR spectrum (DMSO-d6), δ, ppm:
27.66 d (NH–CH2–CH2–CH2–CH2–NH, J 5.0 Hz),
34.25 (endo-CH2–CH–NH), 35.13 (exo-CH2–CH–NH),
39.00 d (NH–CH2–CH2–CH2–CH2–NH, J 12.5 Hz),
40.33 (endo-CH–CH2–CH–NH), 42.04 (exo-CH–CH2–
CH–NH), 45.52 (endo-CH–NH), 46.05 (exo-CH–NH),
48.00 (endo- + exo-CH2bridgehead), 49.07 (endo-CH–CH–NH),
49.71 (exo-CH–CH–NH), 132.10 (endo-CH=CH),
N-[(Adamantan-2-yl)methyl]-N'-(bicyclo[2.2.1]-
hept-5-en-2-yl)urea (4c) was prepared similarly to
compound 4a from 0.25 g (1.85 mmol) of isocyanate
2b, 0.31 g (1.87 mmol) of 1-(aminomethyl)adaman-
tane, and 0.145 g (1.43 mmol, 0.2 mL) of TEA in
5 mL of anhydrous DMF. Yield 0.45 g (82%), mp
1
223–224°C. Н NMR spectrum (DMSO-d6), δ, ppm:
0.52 d.t (1H, endo-CH–СH2–CH–NH, J1 11.8 Hz, J2
3.3 Hz), 1.08 d.t (1H, exo-CH–СH2–CH–NH), 1.28 q
(2Н, endo-CH2, J 8.4 Hz), 1.39 d (6H, Ad, J 9.5 Hz),
1.50 q (2Н, exo-CH2, J 8.4 Hz), 1.62 d.d (6H, Ad, J1
44.2 Hz, J2 11.8 Hz), 2.01–2.07 m (1H, endo-CH–CH–
NH), 2.57 s (1H, endo-CH–СH2–CH–NH), 2.64–2.73
m (1H, exo-CH–CH–NH), 2.75 s (1H, exo-CH–СH2–
CH–NH), 2.78 s (1H, endo-CH–СH2–CH–NH), 2.85 s
(1H, exo-CH–СH2–CH–NH), 3.11 s (2H, CH2–Ad),
3.38–3.43 m (1H, endo-CH–NH), 4.11–4.17 m (1H,
exo-CH–NH), 5.30 d (1H, endo-NH, J 8.4 Hz), 5.60 t
(1H, endo NH–CH2–Ad, J 6.2 Hz), 5.69 t (1H, exo-
NH–CH2–Ad, J 6.0 Hz), 5.96 d (1H, exo-NH, J 8.4 Hz),
5.96 q (1H, endo-CH=CH–CH–CH–NH, J 3.3 Hz),
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 55 No. 8 2019