IMIDAZO[4,5ꢀ
a
]QUININDOLINES AS HIGHLY EFFECTIVE
109
1
IR: 2225 (CN); H NMR: 1.66 (3H, t,
CH2CH3), 4.07 (3H, s, CH ), 4.42 (2H, q,
J
J
=7.2, 35.2, 42.7, 104.1, 109.4, 114.0, 115.6, 117.7, 118.7,
= 7.2, 119.1, 120.4, 124.3, 125.3, 129.5, 129.7, 138.2, 141.5,
3
+
CH2CH ), 7.42 (1H, td,
J
= 8.0, 0.8, ArH), 7.51 (1H, 142.4, 144.2, 149.5; MS,
m/z: 353 (M ). Calcd. for
3
C H N (353.4): C, 74.77; H, 5.42; N, 19.82. Found:
d, J= 8.4, ArH), 7.72 (1H, td,
J
= 8.0, 1.2, ArH), 7.86
= 9.2, ArH), 8.09 (1H, d,
= 9.2, ArH), 8.22 C, 74.37; H, 5.36; N, 19.50.
1H, s, ArH), 8.90 (1H, d, = 8.0, ArH); C NMR:
4.7, 31.6, 37.7, 104.5, 109.3, 113.3, 116.2, 117.7, dolineꢀ12ꢀcarbonitrile
18.8, 119.0, 120.8, 124.3, 125.1, 129.6, 129.6, 137.3, yellow needles (EtOH), yield 65%, mp 286–289
22 19
5
(1H, d,
J
J
13
(
J
3ꢀButylꢀ7ꢀethylꢀ3,7ꢀdihydroimidazo[4,5ꢀ
IIIh) was obtained as shiny
C;
41.0, 142.4, 144.9, 149.5; MS, m/z: 325 (M ). Calcd. IR: 2225 (CN). H NMR: 1.01 (3H, t,
J = 7.0,
a]quininꢀ
1
1
1
(
°
+
1
for C H N (325.4): C, 73.83; H, 4.65; N, 21.52. CH CH CH CH3), 1.43 (2H, m, CH CH2CH CH3),
20
15
5
2
2
2
2
2
Found: C, 74.06; H, 4.69; N, 21.28.
,7ꢀDiethylꢀ3,7ꢀdihydroimidazo[4,5ꢀ
lineꢀ12ꢀcarbonitrile
IIId) was obtained as shiny yelꢀ CH
low needles (EtOH), yield 65%, mp 295–297
1.59 (3H, t,
J
= 7.2, CH2CH3), 1.98 (2H, m,
7.2,
CH ),
CH2CH2CH CH ), 4.37 (2H, t,
J
=
3
a
]quinindoꢀ
2
CH CH
3
(
2
CH
2
2
), 4.67 (2H, q,
3
J
= 7.2, CH
2
3
°
C; IR: 7.44 (1H, td,
= 7.2, CH2CH3), ArH), 7.72 (1H, td,
= 9.2, ArH), 8.11 (1H, d,
ArH), 8.90 (1H, d, = 8.0, ArH); C NMR: 13.4,
3.7, 20.0, 31.2, 33.6, 42.5, 104.3, 109.6, 114.2, 115.2,
17.4, 118.7, 119.1, 120.5, 124.6, 125.7, 129.2, 129.7,
J
= 8.0, 0.8, ArH), 7.53 (1H, d, J = 8.4,
= 8.0, 1.2, ArH), 7.85 (1H, d,
= 9.2, ArH), 8.18 (1H, s,
1
2
1
225 (CN). H NMR: 1.53 (3H, t,
.66 (3H, t, = 7.2, CH2CH3), 4.35 (2H, q,
= 7.2, CH2CH ), 7.43 (1H,
J
J
J
J
J
J = 7.2,
13
J
CH2CH ), 4.43 (2H, q,
J
3
3
1
1
1
td,
1H, td,
.07 (1H, d,
1H, d, = 8.0, ArH); C NMR: 13.9, 14.5, 32.5,
J
= 8.0, 0.8, ArH), 7.50 (1H, d, J = 8.4, ArH), 7.75
= 8.0, 1.2, ArH), 7.84 (1H, d, = 9.2, ArH),
= 9.2, ArH), 8.23 (1H, s, ArH), 8.91
(
8
J
J
+
38.4, 141.6, 142.4, 144.2, 149.4; MS, m/z: 367 (M ).
Calcd. for C H N (367.4): C, 75.18; H, 5.76; N,
23 21 5
9.06. Found: C, 74.89; H, 5.72; N, 18.84.
J
13
(
J
1
3
1
1
7.5, 104.5, 109.7, 113.1, 116.4, 117.8, 118.2, 119.0,
20.4, 124.4, 125.2, 129.7, 129.8, 137.1, 141.3, 142.6,
+
44.7, 149.5; MS,
m/
z: 339 (M
). Calcd. for C H N
17
21
5
ACKNOWLEDGMENTS
(
339.4): C, 74.32; H, 5.05; N, 20.63. Found: C, 73.97;
H, 5.01; N, 20.45.
ꢀMethylꢀ3ꢀpropylꢀ3,7ꢀdihydroimidazo[4,5ꢀ
We would like to express our sincere gratitude to
Research Office, Mashhad Branch, Islamic Azad
University, MashhadꢀIran, for financial support of this
work.
7
a]quinꢀ
indolineꢀ12ꢀcarbonitrile
(
IIIe). mp 305–307
°
C (lit.
= 7.2,
1
[11] mp 303–305
°
C); H NMR: 1.03 (3H, t,
J
CH CH2CH3), 1.98–2.08 (2H, m, CH2CH2CH ), 4.09
2
3H, s, CH ), 4.35 (2H, t,
3
REFERENCES
(
J
= 7.2, CH2CH CH ), 7.44
3
2
3
(
7
1H, td,
.73 (1H, td,
ArH), 8.12 (1H, d,
.92 (1H, d, = 8.0, ArH).
ꢀEthylꢀ3ꢀpropylꢀ3,7ꢀdihydroimidazo[4,5ꢀ
indolineꢀ12ꢀcarbonitrile IIIf). mp 304–306
C); H NMR: 1.05 (3H, t,
J
= 8.0, 0.8, ArH), 7.53 (1H, d, J = 8.4, ArH),
1. Cimanga, K., DeBruyne, T., Lasure, A., Poel, B.V.,
Pieters, L., Claeys, M., Berghe, D.V., and
Vlietinck, A.J., Planta Med., 1996, vol. 62, pp. 22–27.
J
= 8.0, 1.2, ArH), 7.87 (1H, d,
J
= 9.2,
J
= 9.2, ArH), 8.23 (1H, s, ArH),
8
J
2. Bierer, D.E., Fort, D.M., Mendez, C.D., Luo, J.,
Imbach, P.A., Dubenko, L.G., et al., J. Med. Chem.
998, vol. 41, pp. 894–901.
,
7
a
°
]quinꢀ
C (lit.
1
(
3
. Abblordeppey, S.Y., Fan, P., Clark, A.M., and
Nimrod, A., Bioorg. Med. Chem., 1999, vol. 7, pp. 343–
349.
1
[11] mp 303–306
°
J
= 7.2,
CH CH2CH3), 1.57 (3H, t,
J
= 7.2, CH2CH3), 2.00–
2
.09 (2H, m,
2
J
7
J = 7.2, CH2CH2CH ), 4.35 (2H, t,
3
4. Molina, A., Vaquero, J.J., GarciaꢀNavio, J.L., Alvarezꢀ
Builla, J., de PascualꢀTeresa, B., Gago, F.,
Rodrigo, M.M., and Ballesteros, M., J. Org. Chem.,
= 7.2, CH2CH CH ), 4.69 (2H, q,
J
= 7.2, CH2CH ),
3
2
3
.43 (1H, td,
J
= 8.0, 0.8, ArH), 7.55 (1H, d, J = 8.4,
= 8.0, 1.2, ArH), 7.87 (1H, d,
= 9.2, ArH), 8.11 (1H, d, = 9.2, ArH), 8.21 (1H, s,
ArH), 8.95 (1H, d, = 8.0, ArH).
ꢀButylꢀ7ꢀmethylꢀ3,7ꢀdihydroimidazo[4,5ꢀ
dolineꢀ12ꢀcarbonitrile IIIg) was obtained as shiny yeꢀ
llow needles (EtOH), yield 64%, mp 296–298 C; IR:
= 7.0,
CH CH CH CH3), 1.45 (2H, m, CH CH CH CH3),
1996, vol. 61, pp. 5587–5599.
ArH), 7.72 (1H, td,
J
J
J
5. Atia, A.J.K., Molecules, 2009, vol. 14, pp. 2431–2446.
J
6. KhalafiꢀNezhad, A., Soltani, R.M.N., Mohabatkar, H.,
Asrari, Z., and Hemmateenejad, B., Bioorg. Med.
Chem., 2005, vol. 13, pp. 1931–1938.
3
a]quininꢀ
(
7
8
9
. Karakurt, A., Dalkara, S., Özalp, M., Özbey, S.,
Kendi, E., and Stables, J.P., Eur. J. Med. Chem., 2001,
vol. 36, pp. 421–433.
. Suzuki, F., Kuroda, T., Tamura, T., Soichiro, S., Ohmꢀ
ori, K., and Ichikawa, S., J. Med. Chem., 1992, vol. 35,
pp. 2863–2870.
°
1
2
225 (CN). H NMR: 1.01 (3H, t, J
2
2
2
2
2
2
1
4
J
.99 (2H, m, CH2CH2CH CH ), 4.09 (3H, s, CH ),
2 3 3
.37 (2H, t,
= 8.0, 0.8, ArH), 7.52 (1H, d, J = 8.4, ArH), 7.72
= 8.0, 1.2, ArH), 7.86 (1H, d, = 9.2, ArH),
.10 (1H, d, = 9.2, ArH), 8.19 (1H, s, ArH), 8.91
1H, d, = 8.0, ArH); C NMR: 13.5, 20.0, 33.5,
J = 7.2, CH2CH CH CH ), 7.43 (1H, td,
2 2 3
. Vijesh, A.M., Isloor, A.M., Telkar, S., Arulmoli, T., and
Fun, H.K., Arab. J. Chem., 2013, vol. 6, pp. 197–204.
(1H, td,
J
J
8
(
J
1
0. Bhatnagar, A., Sharma, P.K., and Kumar, N., Int.
13
J
J. PharmTech. Res., 2011, vol. 3, pp. 268–282.
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY Vol. 42
No. 1
2016