REACTIONS OF N- AND C-ALKENYLANILINES: IV.
1529
Table 2. 1H NMR spectra of compounds IV, VIII, IX, XI, XIV XVI, XVIII XXI, XXIII, XXIV, XXVI XXXVI,
and XL XLIX in CDCl3
Comp.
no.
Chemical shifts , ppm (J, Hz)
IV
1.92 q (2H, CH2, J = 7.46), 2.02 s (3H, CH3), 2.43 2.62 m (4H, 2CH2), 3.69 s (3H, OCH3), 5.85 s
(1H, CH), 6.63 6.71 m (3H, Harom), 7.71 s (1H, NH)
VIII
IX, XIa
1.72 2.53 m (6H, 3CH2), 2.63 s (3H, CH3), 3.13 br.s (1H, OH), 3.80 s (3H, OCH3), 4.45 br.s
(1H, CHO), 6.70 s (1H, 5-H), 6.77 d (1H, 7-H, J = 8.44), 7.49 d (1H, 8-H, J = 8.51)
1.96 q (2H, CH2, J = 7.40), 2.13 s (1H, CH3), 2.20 s and 2.24 s (3H, CH3), 2.28 s and 2.32 s (3H,
CH3), 2.49 d.t (2H, CH2, J1 = 1.98, J2 = 7.35), 2.61 d.t (2H, CH2, J1 = 1.84, J2 = 7.34), 5.82 t (J = 2.00),
5.96 t (J = 2.04), 6.94 d (1H, 5-H, J = 4.20), 7.00 d (1H, 3-H, J = 5.83)
1.90 q (2H, CH2, J = 7.34), 1.23 s (3H, CH3), 2.41 2.60 m (4H, 2CH2), 3.72 s (3H, OCH3), 4.12 q (2H,
OCH2, J = 7.19), 5.78 s (1H, CH), 6.61 6.72 m (3H, Harom), 7.85 s (1H, NH)
1.20 t (3H, CH3, J = 7.02), 1.92 q (2H, CH2, J = 7.38), 2.44 t.d (2H, CH2, J1 = 7.33, J2 = 2.35), 2.64 t.d
(2H, CH2, J1 = 7.33, J2 = 2.60), 3.74 s (3H, CH3), 4.11 q (2H, OCH2, J = 7.15), 5.94 t (1H, CH, J =
1.95), 6.33 s (1H, NH), 6.74 d (2H, Harom, J = 7.27), 6.88 d (1H, Harom, J = 7.88), 7.12 t (1H, Harom, J =
8.04)
XIV
XV
XVI
1.32 t (3H, CH3, J = 7.19), 1.67 1.84 m (4H, 2CH2), 2.21 s (4H, 2CH2), 4.23 q (2H, OCH2, J = 7.18),
5.74 s (1H, CH), 6.95 7.08 m (3H, Harom), 7.23 t (1H, Harom, J = 6.86), 8.07 s (1H, NH)
1.71 2.19 m (4H, 2CH2), 2.28 s (3H, CH3), 2.4 2.6 m (2H, CH2), 3.31 br.s (1H, OH), 4.19 d (1H, CHO,
J = 7.17), 6.96 t (1H, Harom, J = 7.54), 7.09 d (2H, Harom, J = 9.01), 8.70 s (1H, NH)
1.44 2.12 m (4H, 2CH2), 2.20 2.42 m (2H, CH2), 3.56 br.s (1H, OH), 3.55 s (3H, OCH3),
3.88 br.s (1H, CHO), 6.62 6.77 m (3H, Harom), 9.69 s (1H, NH)
1.72 2.32 m (4H, 2CH2), 2.28 2.51 m (2H, CH2), 3.03 br.s (1H, OH), 3.78 s (3H, OCH3),
4.12 d (1H, CHO, J = 4.76), 6.78 d (1H, Harom, J = 7.99), 6.80 d (1H, Harom, J = 7.83), 6.93 t (1H, 6-H,
J = 7.95), 7.57 s (1H, NH)
XVIII
XIXb
XX
XXIb
1.01 2.22 m (8H, 4CH2), 3.56 s (1H, CHO), 4.66 br.s (1H, OH), 6.64 d (2H, Harom, J = 7.51),
6.8 7.0 m (2H, Harom), 9.72 s (1H, NH)
XXIII
1.36 t (3H, CH3, J = 7.12), 1.7 2.3 m (4H, 2CH2), 2.4 2.6 m (2H, CH2), 2.73 br.s (1H, OH),
3.86 s (3H, OCH3), 4.14 d (1H, CHOH, J = 4.62), 4.40 q (2H, OCH2, J = 6.95), 6.82 d (1H, Harom, J =
6.57), 6.84 d (1H, Harom, J = 7.33), 7.02 t (1H, 6-H, J = 8.06)
XXIV
XXVI
1.20 t (3H, CH3, J = 6.11), 1.93 q (2H, CH2, J = 7.28), 2.12 s (3H, CH3), 2.42 2.57 m (4H, 2CH2),
4.08 q (2H, CH2O, J = 7.01), 5.67 s (1H, CH), 6.72 7.03 m (3H, Harom), 7.69 br.s (1H, NH)
1.38 t (3H, CH3, J = 7.12), 1.54 1.71 m (2H, CH2), 1.74 1.90 m (2H, CH2), 2.18 2.39 m (2H, CH2),
2.32 s (3H, CH3), 3.52 3.62 m (1H, CH), 4.38 q (2H, CH2, J = 6.7), 6.87 7.20 m (3H, Harom), 7.50 br.s
(1H, OH)
XXVII
2.02 q (2H, CH2, J = 7.43), 2.58 br.s (2H, CH2), 2.66 br.s (2H, CH2), 2.33 s (3H, CH3), 5.89 s (1H,
CH), 7.00 s (1H, NH), 7.11 t (1H, 5-H, J = 7.64), 7.22 7.28 m (2H, 6-H, 4-H), 7.56 d (1H, 3-H, J =
8.02)
XXVIII 1.55 1.86 m (2H, CH2), 2.12 2.57 m (4H, 2CH2), 3.06 s (3H, CH3), 3.59 d.d (1H, CH, J1 = 4.24, J2 = 8.85),
4.34 s (1H, OH), 7.02 t (1H, Harom, J = 7.38), 7.14 7.27 m (3H, Harom
)
XXIX,
XXX,
1.55 2.76 m (CH2), 2.89 s (CH3), 3.04 s (CH3), 3.06 s (CH3), 3.12 s (CH3), 3.15 s (CH3), 3.58 s (OCH),
4.42 d (OCH, J = 6.09), 3.93 s (OCH), 6.06 d ( CH, J = 2.45), 7.05 7.66 m (Harom), 8.83 s (NH), 9.12 s
(NH), 9.38 s (NH)
XXXIa
XXXII
1.92 q (2H, CH2, J = 7.32), 2.29 t.d (2H, CH2, J1 = 7.53, J2 = 2.12), 2.36 s (3H, CH3), 2.50 t.d (2H, CH2,
CH2, J1 = 7.56, J2 = 2.30), 5.57 t (1H, CH, J = 1.98), 7.04 7.22 m (7H, Harom, NH), 7.62 d (2H, Harom
J = 8.27)
,
XXXIII 1.50 1.72 m (2H, CH2), 1.97 2.31 m (4H, 2CH2), 2.38 s (3H, CH3), 2.97 s (1H, OH), 3.09 s (3H, OCH3),
3.81 s (1H, CHO), 7.00 7.14 m (2H, Harom), 7.26 d (2H, Harom, Ts, J = 8.01), 7.56 7.68 m (2H, Harom),
7.83 d (2H, Harom, Ts, J = 8.05), 9.20 br.s (1H, NH)
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 38 No. 10 2002