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3.2.6. E-2-(5,6-dimethyl-1H-benzotriazol-1-yl)-3-(4-trifluo-
romethylphenyl)acrylonitrile (5f)
H-4), 8.05–7.83 (m, 5H, H-6 + H-7 + H-2′ + H-6′ + vinyl-H),
7.06 (d, 2H, J = 8.8 Hz, H-3′ + H-5′), 3.93 (s, 1H, CH3); MS:
m/z 344 (M+). Anal. C17H11F3N4O (C, H, N).
This compound was obtained in 77% yield starting from
2b and 4-trifluoromethylbenzaldehyde (4f), after 47 h under
1
3.2.12. E-2-(5,6-dimethyl-1H-benzotriazol-1-yl)-3-(3,4-
methylenedioxyphenyl)acrylonitrile (5l)
reflux; m.p. 153–154 °C (acetone); H NMR (CDCl3): d
8.05–8.00 (m, 3H, vinyl-H + H-3′ + H-5′), 7.89 (s, 1H, H-4),
7.80 (d, 2H, J = 8.0 Hz, H-2′ + H-6′), 7.71 (s, 1H, H-7), 2.49
(s, 3H, CH3), 2.46 (s, 3H, CH3); MS: m/z 342 (M+). Anal.
C18H13F3N4 (C, H, N).
This compound was obtained in 40% yield from 2b and
3,4-(methylenedioxy)benzaldehyde (4l), after 96 h under re-
flux; m.p. 181–183 °C (acetone); 1H NMR (CDCl3): d 7.85
(s, 1H, H-4), 7.77 (s, 1H, vinyl-H), 7.61 (dd, 1H, J = 8.2 and
1.6 Hz, H-6′), 7.35–7.30 (m, 2H, H-7 + H-2′), 6.94 (d, 1H,
J = 8.2 Hz, H-5′), 6.11 (s, 2H, CH2), 2.47 (s, 3H, CH3), 2.44
(s, 3H, CH3); MS: m/z 318 (M+). Anal. C18H14N4O2 (C, H,
N).
3.2.7. E-2-(5,6-dimethyl-1H-benzotriazol-1-yl)-3-(3-nitro-
phenyl)acrylonitrile (5g)
This compound was obtained in 59% yield starting from
2b and 3-nitrobenzaldehyde (4g), after 24 h under reflux;
m.p. 158–160 °C (acetone); 1H NMR (CDCl3): d 8.69 (s, 1H,
H-2′), 8.41–8.29 (m, 2H, H-4′ + H-5′), 8.06 (s, 1H, vinyl-H),
7.89 (s, 1H, H-4), 7.79 (d, 1H, J = 8.0 Hz, H-6′), 7.72 (s, 1H,
H-7), 2.50 (s, 3H, CH3), 2.46 (s, 3H, CH3); MS: m/z 319
(M+). Anal. C17H13N5O2 (C, H, N).
3.2.13. E-2-(5-trifluoromethyl-1H-benzotriazol-1-yl)-3-
(3,4-methylenedioxyphenyl)acrylonitrile (5m)
This compound was obtained in 45% yield starting from
2c and 3,4-(methylenedioxy)benzaldehyde (4l) heated for
24 h under reflux, then an extra portion of 4l was added and
the reflux continued for an additional 4 h; m.p. 165–166 °C
(diethyl ether); 1H NMR (CDCl3): d 8.47 (s, 1H, H-4), 8.03
(d, 1H, J = 8.8 Hz, H-6), 7.88–7.83 (m, 2H, H-7 + vinyl-H),
7.63 (d, 1H, J = 1.6 Hz, H-2′), 7.36 (dd, 1H, J = 8.4 and
1.6 Hz, H-6′), 6.96 (d, 1H, J = 8.0 Hz, H-5′), 6.13 (s, 2H,
CH2); MS: m/z 358 (M+). Anal. C17H9F3N4O2 (C, H, N).
3.2.8. E-2-(5,6-dimethy-1H-benzotriazol-1-yl)-3-(3-trifluo-
romethylphenyl)acrylonitrile (5h)
This compound was obtained in 57% yield starting from
2b and 3-trifluoromethylbenzaldehyde (4h), after 25 h under
reflux; m.p. 138–139 °C (acetone); 1H NMR (CDCl3): d 8.18
(d, 1H, J = 8.0 Hz, H-4′), 8.07 (s, 1H, H-2′), 8.00 (s, 1H,
vinyl-H), 7.86 (s, 1H, H-4), 7.81–7.69 (m, 3H, H-7 + H-5′ +
H-6′), 2.49 (s, 3H, CH3), 2.45 (s, 3H, CH3); MS: m/z 342
(M+). Anal. C18H13F3N4 (C, H, N).
3.2.14. E-2-(2H-benzotriazol-2-yl)-3-(2-iodophenyl)acry-
lonitrile (7a)
This compound was obtained in 51% yield starting from
3a and 2-iodobenzaldehyde (6a), after 28 h under reflux;
m.p. 148–149 °C (acetone/hexane); H NMR (CDCl3): d
3.2.9. E-2-(5-trifluoromethyl-1H-benzotriazol-1-yl)-3-(3-
nitrophenyl)acrylonitrile (5i)
1
8.68 (s, 1H, vinyl-H), 8.07–7.90 (m, 4H, H-4 + H-7 + 2 phe-
nyl-H), 7.57–7.44 (m, 3H, H-5 + H-6 + 1 phenyl-H), 7.21 (t,
1H, J = 7.8 Hz, H-5′); MS: m/z 372 (M+).Anal. C15H9IN4 (C,
H, N).
This compound was obtained in 48% yield starting from
2c and 3-nitrobenzaldehyde (4g), after reflux for 24 h; m.p.
168–170 °C (diethyl ether); 1H NMR (CDCl3): d 8.73 (d, 1H,
J = 1.0 Hz, H-4), 8.50 (d, 1H, J = 0.8 Hz, H-2′), 8.43 (dd, 1H,
J = 8.0 and 1.0 Hz, H-6), 8.34 (dd, 1H, J = 8.0 and 0.8 Hz,
H-7), 8.17 (s, 1H, vinyl-H), 8.14 (d, 1H, J = 8.8 Hz, H-4′),
7.92 (dd, 1H, J = 8.8 and 0.8 Hz, H-6′), 7.80 (t, 1H,
J = 8.0 Hz, H-5′); MS: m/z 359 (M+).Anal. C16H8F3N5O2 (C,
H, N).
3.2.15. E-2-(2H-benzotriazol-2-yl)-3-(3-fluorophenyl)acry-
lonitrile (7b)
This compound was obtained in 50% yield starting from
3a (1.2 g, 8.0 mmol) and 3-fluorobenzaldehyde (6b) heated
for 24 h under reflux, then an extra portion of 6b was added
and the reflux continued for an additional 4 h; m.p. 152–
153 °C (acetone/hexane); 1H NMR (CDCl3): d 8.48 (s, 1H,
vinyl-H), 7.95–7.88 (m, 2H, H-4 + H-7), 7.78–7.68 (m, 2H,
H-4′ + H-6′), 7.57–7.45 (m, 3H, H-5 + H-6 + H-2′), 7.26 (t,
1H, J = 8.2 Hz, H-5′); MS: m/z 264 (M+). Anal. C15H9FN4
(C, H, N).
3.2.10. E-2-(6-trifluoromethyl-1H-benzotriazol-1-yl)-3-(3-
nitrophenyl)acrylonitrile (5j)
This compound was obtained in 67% yield from 2d and
3-nitrobenzaldehyde (4g), after 16 h under reflux; m.p. 172–
1
173 C (acetone/hexane); H NMR (CDCl3): d 8.72 (d, 1H,
J = 1.0 Hz, H-7), 8.46–8.29 (m, 5H, H-4 + H-5 + H-2′ + H-4′
+ H-6′), 8.23 (s, 1H, vinyl-H), 7.81 (t, 1H, J = 8.0 Hz, H-5′);
MS: m/z 359 (M+). Anal. C16H8F3N5O2 (C, H, Cl, N).
3.2.16. E-2-(5,6-dimethyl-2H-benzotriazol-2-yl)-3-(3,4-
dimethoxyphenyl)acrylonitrile (7c)
3.2.11. E-2-(5-trifluoromethyl-1H-benzotriazol-1-yl)-3-(4-
methoxyphenyl)acrylonitrile (5k)
This compound was obtained in 25% yield from 3c and
4-methoxybenzaldehyde (4e), after 40 h under reflux; m.p.
126–127 °C (diethyl ether); 1H NMR (CDCl3): d 8.46 (s, 1H,
This compound was obtained in 52% yield from 3b and
3,4-dimethoxybenzaldehyde (6c), after 48 h under reflux;
m.p. 179–180 °C (acetone); 1H NMR (CDCl3): d 8.37 (s, 1H,
vinyl-H), 7.73 (d, 1H, J = 1.8 Hz, H-2′), 7.63 (s, 2H, H-4 +
H-7), 7.47 (dd, 1H, J = 8.0 and 1.8 Hz, H-6′), 6.97 (d, 1H,