2134
GRACHEV et al.
3
3
m (4H, NCH2), 3.59 q (2H, CHC6H4, JHH 7.2), 7.08 d
3JHH 7.6], 7.45 t [4H, C6HparaC(O), JHH 7.9], 7.80 d
3
(4H, C6HorthoCH2, JHH 7.4), 7.16 d (4H, C6HmetaCH2,
[2H, C6HorthoC(O), 3JHH 7.7], 8.13–8.21 br.s (2H, NH).
Found, %: C 48.29, H 6.17. C102H160N2O72. Calculated,
%: C 47.74, H 6.28.
3JHH 7.6), 8.15 br.s (2H, NH). Found, %: C 50.26, H
6.64. C113H182N2O72. Calculated, %: C 49.89, H 6.74.
Inclusion compound of β-cyclodextrin with N,N'-
bis[1-(4-isobutylphenyl)propionyl]-1,4-butylene-
diamine (XIX). Obtained similarly to the synthesis of
the inclusion compound XVIII from 0.20 g of β-cyclo-
dextrin and 0.041 g of diamide V. Yield 0.11 g (47%),
Inclusion compound of β-cyclodextrin with O,O'-
dibenzoyl-1,2-ethylendiol (XXII). Obtained similarly
to the synthesis of the inclusion compound XVIII
from 0.20 g of β-cyclodextrin and 0.024 g of diester
XV. Yield 0.13 g (58%), mp 250–252°C (decomp.), Rf
1
1
mp 289–291°C (decomp.), Rf 0.58 (E). H NMR
0.75 (H). H NMR spectrum (DMSO-d6), δ, ppm
spectrum (DMSO-d6), δ, ppm (J, Hz): β-cyclodextrin,
3.28–3.68 m (84H, C2H–C5H, C6H2), 4.41–4.50 m
(14H, C6OH), 4.75–4.82 br.s (14H, C1H), 5.63–5.71
br.s (14H, C3OH), 5.74–5.79 br.s (14H, C2OH);
(J, Hz): β-cyclodextrin, 3.22–3.68 m (84H, C2H–C5H,
C6H2), 4.37–4.43 m (14H, C6OH), 4.76–4.84 br.s (14H,
C1H), 5.60–5.72 br.s (14H, C2OH, C3OH); diester XV,
4.55–4.62 br.s (4H, CH2O), 7.49 t [4H, C6HmetaC(O),
3
3
diamide V: 0.80 d [12H, CH(CH3)2, JHH 6.4], 1.21–
3JHH 7.8], 7.62 t [4H, C6HparaC(O), JHH 7.8], 7.93 d
3
1.32 m (10H, CHCH3, NCH2), 1.69–1.82 m [2H,
[2H, C6HorthoC(O), JHH 7.7]. Found, %: C 47.74, H
CH(CH3)2], 2.35 d (4H, CH2C6H4, 3JHH 7.3), 3.18–3.26
5.98. C100H154N2O74. Calculated, %: C 47.28, H 6.11.
3
m (4H, NCH2), 7.01 d (4H, C6HorthoCH2, JHH 7.4),
Inclusion compound of β-cyclodextrin with O,O'-
bis[1-(4-isobutylphenyl)propionyl]-1,2-ethylendiol
(XXIII). Obtained similarly to the synthesis of the
inclusion compound XVIII from 0.20 g of β-cyclo-
dextrin and 0.039 g of diester VII. Yield 0.071 g
7.14 d (4H, C6HmetaCH2, 3JHH 7.6), 7.82–7.88 br.s (2H,
NH). Found, %: C 50.41, H 6.69. C114H184N2O72.
Calculated, %: C 50.07, H 6.78.
Inclusion compound of β-cyclodextrin with N,N'-
bis(acetylsalicyl)-1,5-pentylenediamine (XX). Ob-
tained similarly to the synthesis of the inclusion
compound XVIII from 0.20 g of β-cyclodextrin and
0.038 g of diamide X. Yield 0.15 g (61%), mp 243–
1
(51%), mp 259–261°C (decomp.), Rf 0.56 (E). H
NMR spectrum (DMSO-d6), δ, ppm (J, Hz): β-
cyclodextrin, 3.23–3.75 m (42H, C2H–C5H, C6H2),
4.03–4.12 m (7H, C6OH), 4.75–4.88 br.s (7H, C1H),
5.42–5.57 br.s (7H, C2OH, C3OH); diester VII, 0.83 d
1
246°C (decomp.), Rf 0.73 (F). H NMR spectrum
3
3
(DMSO-d6), δ, ppm (J, Hz): β-cyclodextrin, 3.25–3.72
m (84H, C2H–C5H, C6H2), 4.07–4.16 m (14H, C6OH),
4.78–4.87 br.s (14H, C1H), 5.35–5.46 br.s (14H,
C2OH, C3OH); diamide X, 1.30–1.40 m (2H,
NCH2CH2CH2), 1.45–1.57 m (4H, NCH2CH2), 2.18 s
[6H, C(O)CH33], 3.15–3.23 m (4H, NCH2), 7.12 d [2H,
[12H, CH(CH3)2, JHH 6.7], 1.42 d (6H, CHCH3, JHH
6.8), 1.75–1.87 m [2H, CH(CH3)2], 2.41 d (4H,
CH2C6H4), 3.63–3.72 m (2H, CHC6H4), 7.04 d ( 4H,
3
3
C6HorthoCH2, JHH 7.8), 7.13 d (4H, C6HmetaCH2, JHH
7.7). Found, %: C 52.88, H 7.04. C70H108O39.
Calculated, %: C 53.43, H 6.92.
3
C6HorthoC(O), JHH 7.8], 7.27 t [2H, C6HparaC(O), JHH
Inclusion compound of β-cyclodextrin with N,N'-
bis(acetylsalicyl)-1,4-butylenediamine (XXIV). Ob-
tained similarly to the synthesis of the inclusion
compound XVIII from 0.20 g of β-cyclodextrin and
0.036 g of diamide IX. Yield 0.07 g (49%), mp 275–
3
7.3], 7.44 t [2H, C6HmetaC(O), JHH 7.8], 7.62 d [2H,
3
C6HorthoOC(O), JHH 7.8], 7.78–7.85 br.s (2H, NH).
Found, %: C 48.17, H 6.16. C107H166N2O76. Calculated,
%: C 47.66, H 6.21.
1
Inclusion compound of β-cyclodextrin with N,N'-
dibenzoyl-1,4-butylenediamine (XXI). Obtained
similarly to the synthesis of the inclusion compound
XVIII from 0.20 g of β-cyclodextrin and 0.026 g of
diamide XIII. Yield 0.13 g (57%), mp 279–282°C
277°C (decomp.), Rf 0.66 (E). H NMR spectrum
(DMSO-d6), δ, ppm (J, Hz): β-cyclodextrin, 3.25–3.71
m (42H, C2H–C5H, C6H2), 4.11–4.19 m (7H, C6OH),
4.75–4.84 br.s (7H, C1H), 5.38–5.49 br.s (7H, C2OH,
C3OH); diamide IX, 1.50–1.60 m (4H, NCH2CH2),
2.16 br.s [6H, C(O)CH3], 3.16–3.22 m (4H, NCH2),
1
(decomp.), Rf 0.47 (G). H NMR spectrum (DMSO-
3
d6), δ, ppm (J, Hz): β-cyclodextrin, 3.26–3.71 m (84H,
C2H–C5H, C6H2), 4.06–4.15 m (14H, C6OH), 4.76–
4.84 br.s (14H, C1H), 5.45–5.54 br.s (14H, C2OH,
C3OH); diamide XIII, 1.55–1.62 m (4H, NCH2CH2),
3.55–3.62 br.s (4H, NCH2), 7.40 t [4H, C6HmetaC(O),
7.11 d [2H, C6HorthoC(O), JHH 7.6], 7.26 t [2H,
3
3
C6HparaC(O), JHH 7.7], 7.45 t [2H, C6HmetaC(O), JHH
7.4], 7.62 d [2H, C6HorthoOC(O), 3JHH 7.6], 7.92–7.01 br.s
(2H, NH). Found, %: C 50.18, H 5.97. C64H94N2O41.
Calculated, %: C 49.68, H 6.12.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 81 No. 10 2011