ASPARTIC ACID AS A HIGHLY EFFICIENT AND NONTOXIC ORGANOCATALYST
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-(4-Chlorophenyl)-1-(4-methylphenyl)-4,5-di-
5. Dutta, S., Mariappan, G., Roy, S., and Verma, M.,
1
Indian Drugs, 2009, vol. 46, p. 50.
phenyl-1H-imidazole (3h). H NMR (400 MHz,
CDCl ), δ, ppm: 2.36 s (3H), 6.94 d (2H, J = 8 Hz),
6. Sengupta, A.K. and Bhattacharya, T., J. Indian Chem.
Soc., 1983, vol. 60, p. 373.
3
7
.10 d (2H, J = 8 Hz), 7.15–7.17 m (2H), 7.20–7.30 m
(
8H), 7.41 d (2H, J = 8.4 Hz), 7.62 d (2H, J = 8.4 Hz).
7. Navidpour, L., Shadnia, H., Shafaroodi, H., Amini, M.,
1
3
Dehpour, A.R., and Shafiee, A., Bioorg. Med. Chem.,
C NMR spectrum (100 MHz, CDCl ), δ , ppm: 21.2,
3
C
2
007, vol. 15, p. 1976.
1
1
1
26.7, 127.4, 128.0, 128.1, 128.2, 128.3, 128.4, 129.1,
29.8, 130.1, 130.5, 131.1, 131.2, 134.2, 134.3, 138.3,
38.5, 145.8.
8
. Fluoret, G., J. Med. Chem., 1970, vol. 13, p. 843.
9. Brogden, R.N., Heel, R.C., Speight, T.M., and
Avery, G.S., Drugs, 1978, vol. 16, p. 387.
1
-(4-Chlorophenyl)-2-(4-methoxyphenyl)-4,5-di-
1
10. Brimblecombe, R.W., Duncan, W.A.M., Durant, G.J.,
Emmett, J.C., Ganellin, C.R., and Parsons, M.E., J. Int.
Med. Res., 1975, vol. 3, p. 86.
phenyl-1H-imidazole (3i). H NMR (400 MHz,
CDCl ), δ, ppm: 3.19 s (3H), 6.83 d (2H, J = 8.8 Hz),
6
7
8
ppm: 55.3, 113.7, 122.8, 126.7, 127.4, 128, 128.2,
1
1
3
.99 d (2H, J = 8.4 Hz), 7.14–7.16 m (2H), 7.20–
.32 m (8H), 7.37 d (2H, J = 8.8 Hz), 7.62 d (2H, J =
1
1. Hunkeler, W., Mohler, H., Pieri, L., Polc, P., Bo-
netti, E.P., Cumin, R., Schaffner, R., and Haefely, W.,
Nature, 1981, vol. 290, p. 514.
1
3
.4 Hz). C NMR spectrum (100 MHz, CDCl ), δ ,
3
C
1
1
1
1
1
2. Murry, J.A., Curr. Opin. Drug Discovery Dev., 2003,
28.3, 129.3, 129.7, 130.3, 130.4, 130.5, 131.1, 134,
34.3, 135.8, 138.2, 147.0, 159.4.
vol. 6, p. 945.
3. Murthy, S.M., Madhav, B., and Nageswar, Y.V.D.,
2
-(4-Methoxyphenyl)-4,5-diphenyl-1H-imidazole
Tetrahedron Lett., 2010, vol. 51, p. 5252.
1
(
4d). H NMR spectrum (400 MHz), δ, ppm: in
4. Schubert, H. and Stodolka, H., J. Prakt. Chem., 1963,
DMSO-d : 3.82 s (3H), 7.06 d (2H, J = 8.8 Hz),
7
8
vol. 22, p. 130.
6
.37 m (6H), 7.52 d (4H, J = 6.4 Hz), 8.03 d (2H, J =
.8 Hz), 12.5 br.s (1H); in DMSO-d + D O: 3.83 s
5. Tsuji, J., Sakai, K., Nemoto, H., and Nagashima, H.,
6
2
J. Mol. Catal., 1983, vol. 18, p. 169.
(
3H), 7.03 d (2H, J = 8.8 Hz), 7.28 m (2H), 7.35 m
4H), 7.47 d (4H, J = 7.2 Hz), 8.01 d (2H, J = 8.8 Hz).
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(
1
3
C NMR spectrum (100 MHz, DMSO-d , δ ,
6
C
ppm: 55.6, 114.6, 123.2, 127.3, 127.7, 128.2, 128.9,
46.2, 159.9.
-(Naphthalen-2-yl)-4,5-diphenyl-1H-imidazole
17. Japp, F.R. and Robinson, H.H., Ber., 1882, vol. 15,
1
p. 1268.
1
1
2
2
2
2
2
8. Wasserman, H.H., Long, Y.O., Zhang, R., and Parr, J.,
2
1
Tetrahedron Lett., 2002, vol. 43, p. 3351.
(
4h). H NMR spectrum (400 MHz, DMSO-d ), ppm:
6
9. Liu, J., Chem, J., Zhao, J., Zhao, Y., Li, L., and
7
1
8
.26 t (1H, J =14 Hz), 7.35 m (2H), 7.41 t (1H, J =
4 Hz), 7.46–7.49 m (2H), 7.55–7.62 m (7H), 7.95–
.04 m (3H), 8.27 d (1H, J = 8.4 Hz), 8.63 s (1H).
C NMR spectrum (100 MHz, DMSO-d ), δ , ppm:
Zhang, H., Synthesis, 2003, p. 2661.
0. Weinmann, H., Harre, M., Koeing, K., Merten, E., and
1
3
Tilestam, U., Tetrahedron Lett., 2002, vol. 43, p. 593.
6
C
1. Sarshar, S., Siev, D., and Mjalli, A.M.M., Tetrahedron
Lett., 1996, vol. 37, p. 835.
1
1
1
23.9, 124.2, 126.8, 127.1, 127.2, 127.6, 128.2, 128.3,
28.6, 128.7, 128.8, 128.9, 129.2, 130, 131.4, 133.2,
33.5, 135.6, 137.9, 138.5, 145.9.
2. Tshoar, R.H., Jahanbakhshi, H., Mousavizadeh, F., and
Rahnamafar, R., Gazi Univ. J. Sci., 2012, vol. 25, p. 29.
Financial support for this work by the Ilam
University (Ilam, Iran) is gratefully acknowledged.
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mi, M., Darvishi, K., and Gholamnia, L., Collect.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 3 2015