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MOLCHANOV et al.
Table 2. (Contd.)
1
Compd.
no.
IR spectrum, cm
1H NMR spectrum, , ppm (J, Hz)
IVe
IVf
Vae
Vb
980, 1020, 1080, 1100, 1160, 1290, 1390 s, 2.32 d (1H, 6), 2.37 d (1H, 6), 2.94 d (1H, 19), 3.04 d (1H, 19),
1490, 1720 v.s, 3050 3.92 s (3H), 7.26 d (2H, 8), 7.63 d (2H, 8)
980, 1110, 1160, 1290, 1390 s, 1510, 1600, 2.32 d (1H, 6), 2.37 d (1H, 6), 2.94 d (1H, 19), 3.04 d (1H, 19),
1720 v.s, 3050
3.92 s (3H), 7.14 7.32 (4H)
1.71 d (1H, 7), 2.68 d (1H, 7), 2.92 d (1H, 19), 3.44 d (1H, 19),
3.82 s (3H), 7.28 7.51 (5H)
1.70 d (1H, 7), 2.39 s (3H), 2.67 d (1H, 7), 2.91 d(1H, 19), 3.42 d
(1H, 19), 3.81 s (3H), 7.15 7.27 (4H)
Vc
1.71 d (1H, 7), 2.42 s (3H), 2.67 d (1H, 7), 2.91 d (1H, 19), 3.43 d
(1H, 19), 3.82 s (3H), 7.11 7.38 (3H)
Vd
1.72 d (1H, 7), 2.67 d (1H, 7), 2.92 d (1H, 19), 3.44 d (1H, 19),
3.82 s (3H), 7.26 7.49 (4H)
Ve
1.72 d (1H, 7), 2.68 d (1H, 7), 2.92 d (1H, 19), 3.44 d (1H, 19),
3.82 s (3H), 7.21 d (2H, 8), 7.63 d (2H, 8)
1.71 d (1H, 7), 2.68 d (1H, 7), 2.92 d (1H, 19), 3.43 d (1H, 19),
3.82 s (3H), 7.14 7.32 (4H)
Vf
VIa
VIbf
VIc
VId
VIe
VIf
VIIa
VIIc
VIIf
980, 1100, 1160, 1290, 1390 s, 1510, 1600, 2.26 d (1H, 6), 2.43 d (1H, 6), 2.89 d (1H, 19), 3.04 d (1H, 19),
1720 v.s, 3050 3.91 s (3H), 7.28 7.53 (5H)
980, 1100, 1160, 1290, 1390c, 1520, 1720v.s, 2.26 d (1H, 6), 2.41 m (4H), 2.87 d (1H, 19), 3.02 d (1H, 19),
3050 3.90 s (3H), 7.22 d (2H, 8), 7.30 d (2H, 8)
870, 970, 1060, 1100, 1160, 1290, 1380 s, 2.26 d (1H, 6), 2.43 m (4H), 2.88 d (1H, 19), 3.02 d (1H, 19),
1500, 1720 v.s, 3050 3.91 s (3H), 7.16 7.39 (3H)
970, 1020, 1090, 1160, 1290, 1380 s, 1500, 2.26 d (1H, 6), 2.42 d (1H, 6), 2.89 d (1H, 19), 3.03 d (1H, 19),
1720 v.s, 3050 3.91 s (3H), 7.31 d (2H, 8), 7.48 d (2H, 8), 7.31 d (2H, 8)
970, 1020, 1080, 1160, 1290, 1380 s 1490, 2.27 d (1H, 6), 2.43 d (1H, 6), 2.89 d (1H, 19), 3.04 d (1H, 19),
1720 v.s, 3050 3.90 s (3H), 7.26 d (2H, 8) 7.63 d (2H, 8)
840, 970, 1100, 1160, 1290, 1390 s, 1520, 2.27 d (1H, 6), 2.43 d (1H, 6), 2.89 d (1H, 19), 3.03 d (1H, 19),
1720 v.s, 3050
3.91 s (3H), 7.17 7.37 (4H)
1.73 d (1H, 7), 2.72 d (1H, 7), 2.96 d (1H, 19), 3.46 d (1H, 19),
3.81 s (3H), 7.28 7.53 (5H)
1.73 d (1H, 7), 2.71 d (1H, 7), 3.45 d (1H, 19), 3.81 s (3H), 7.16
7.39 (3H)
1.74 d (1H, 7), 2.72 d (1H, 7), 2.96 d (1H, 19), 3.45 d (1H, 19),
3.81 s (3H), 7.17 7.37 (4H)
a
1H NMR spectra of compounds IIIa f were registered in DMSO-d6, of the other compounds in CDCl3.
1H NMR spectrum, (CD3)2CO, , ppm (J, Hz): 3.16 d (1H, 19), 3.31 d (1H, 18), 3.33 d (1H, 19), 3.61 d (1H, 18), 3.78 ©(3H),
7.39 d (1H, 9), 7.62 d (1H, 9), 8.18 © (1H).
b
c
d
e
f
13C NMR spectrum, , ppm: 42.0 (C9), 43.7 (C4), 52.5 (CH3æ), 69.4 (C5), 129.6, 129.9, 131.9, 133.8 (C arom), 138.9 (C3),
162.9, 174.3, 177.3 (C=æ).
13C NMR spectrum, , ppm: 28.2 (C2), 32.9 (C3), 35.9 (C7), 49.0 (C1), 54.9 (CH3æ), 126.7, 126.8, 129.2, 132.1 (C arom),
162.9, 173.5, 174.2 (C=æ).
13C NMR spectrum, , ppm: 26.6 (C2), 32.9 (C3), 34.8 (C7), 49.0 (C1), 54.0 (CH3æ), 126.7, 126.8, 129.2, 129.6, 132.1 (C arom),
162.9, 173.5, 174.2 (C=æ).
13C NMR spectrum, , ppm: 21.6 (CH3), 28.2 (C2), 33.6 (C3), 34.7 (C1), 35.4 (C7), 54.7 (CH3), 126.5, 129.8, 130.2, 139.6
(C arom), 167.8, 172.5, 173.9 (C=æ).
more stable isomer. Mixture of isomers IVa and Va
In the IR spectra of esters IVa f, Va f is present
1
was also obtained on treating pyrazoline IIIa with
ICl. The structure and composition of compounds
obtained were established from elemental analyses
and spectral data.
an absorption band in the region of 1720 cm . In the
1H NMR spectra the signals from the methylene
group proton of cyclopropane ring in cis-position to
ester group (H2 in IVa f at 2.4 ppm, and H1 in Va f
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 38 No. 2 2002