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S. Tu, J. Zhang, X. Zhu, Y. Zhang, Q. Wang, J. Xu, B. Jiang, R. Jia, J. Zhang, and F. Shi
Vol 43
and NH2), 2172 (CN), 1665 (C=O), 1598 (C=C) cm-1; 1H NMR:
ꢀ 8.81 (s, 1H, NH), 6.92 (t, 1H, J = 8.2 Hz, ArH), 6.79 (d, 1H, J
= 8.0 Hz, ArH), 6.60 (d, 1H, J = 8.0 Hz, ArH), 5.63 (s, 2H,
NH2), 4.73 (s, 1H, CH), 3.84 (s, 3H, CH3O), 3.78 (s, 3H, CH3O),
2.44 (d, 1H, J = 16.4 Hz, CH2), 2.30 (d, 1H, J = 16.4 Hz, CH2),
2.16 (d, 1H, J = 16.0 Hz, CH2), 1.94 (d, 1H, J = 16.0 Hz, CH2),
1.04 (s, 3H, CH3), 0.95 (s, 3H, CH3).
Anal. Calcd. for C19H21N3O: C, 74.24; H, 6.89; N, 13.67;
Found C, 74.12; H, 6.71; N, 13.52.
2-Amino-4-(2'-thienyl)-3-cyano-7,7-dimethyl-5-oxo-1,4,5,6,7,8-
hexahydroquinoline (4m).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3378, 3321 and 3284 (NH
and NH2), 2198 (CN), 1677 (C=O), 1605 (C=C) cm-1; 1H NMR:
ꢀ 8.98 (s, 1H, NH), 6.85-7.12 (m, 3H, thiophene-CH), 5.85 (s,
2H, NH2), 4.51 (s, 1H, CH), 2.29 (d, 1H, J = 16.8 Hz, CH2), 2.20
(d, 1H, J = 16.8 Hz, CH2), 2.14 (d, 1H, J = 16.0 Hz, CH2), 2.06
(d, 1H, J = 16.0 Hz, CH2), 1.01 (3H, s, CH3), 0.92 (3H, s, CH3).
Anal. Calcd. for C16H17N3OS: C, 64.19; H, 5.72; N, 14.04;
Found C, 64.33; H, 5.60; N, 13.89
Anal. Calcd. for C20H23N3O3: C, 67.57; H, 6.56; N, 11.89;
Found C, 67.64; H, 6.45; N, 11.66.
2-Amino-4-(4'-chlorophenyl)-3-cyano-7,7-dimethyl-5-oxo-1,4,5,
6,7,8-hexahydroquinoline (4i).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3394, 3321 and 3223 (NH
and NH2), 2178 (CN), 1655 (C=O), 1601 (C=C) cm-1; 1H NMR:
ꢀ 8.90 (s, 1H, NH),7.31 (d, 2H, J = 8.0 Hz, ArH), 7.14 (d, 2H, J
= 8.0 Hz, ArH), 5.78 (s, 2H, NH2), 4.32 (s, 1H, CH), 2.42 (d,
1H, J = 16.8 Hz, CH2), 2.31 (d, 1H, J = 16.8 Hz, CH2), 2.17 (d,
1H, J = 16.0 Hz, CH2), 1.99 (d, 1H, J = 16.0 Hz, CH2), 1.02 (s,
3H, CH3), 0.90 (s, 3H, CH3).
REFERENCES AND NOTES
[1] T. Tanaka and F. Toda. Chem. Rev., 100, 1025 (2000).
[2a] L. Weber, K. Illegen and M. Almstetter, Synlett, 366 (1999).
[b] R. W. Armstrong, A. P. Combs, P. A. Tempest, S. D. Brown and T.
A. Keating, Acc. Chem. Rev., 29, 123 (1996).
[3a] A. Strecker, Liebigs Ann. Chem., 75, 27 (1850). [b] S.
Balalaie, M. Bararjanian, A. M. Amani, B. Movassagh Synlett, 263
(2006)
Anal. Calcd. for C18H18ClN3O: C, 69.95; H, 5.53; N, 12.82;
Found C, 70.12; H, 5.41; N, 12.68.
2-Amino-4-(4'-bromophenyl)-3-cyano-7,7-dimethyl-5-oxo-1,4,
5,6,7,8-hexahydroquinoline (4j).
[4] S. A. Galema, Chem. Soc. Rev., 26, 233 (1997).
[5a] J. H. Burkhalter and W. H. Edgerton, J. Am. Chem. Soc., 73,
4837 (1951); [b] P. G. Bray and S. A. Ward, Pharm. Therapeutics, 77, 1
(1998); [c] S. D. Sharad, E. S. Robert and A. Michael, Toxicon, 35, 433
(1997); [d] G. Meilin, N. Tonglan, T. A. Laychoo, K. Kunnika and W.
Prapon, Eur. J. Pharm. Sci., 6, 19 (1998).
[6a] U. Eisner, and J. Kuthan, Chem. Rev., 72, 1 (1972); [b] D. M.
Stout and A. I. Meyers, Chem. Rev. 82, 223 (1982).
[7a] R. J. Chorvat and K. J. Rorig, J. Org. Chem., 53, 5779
(1988); [b] C. O. Kappe and W. M. F. Fabian, Tetrahedron, 53, 2803
(1997); [c] C. O. Kappe, Tetrahedron, 49, 6397 (1993).
This compound was obtained according to above general
procedure; ir (potassium bromide): ꢁ 3392, 3323 and 3223 (NH
and NH2), 2179 (CN), 1656 (C=O), 1600 (C=C) cm-1; 1H NMR:
ꢀ 8.90 (s, 1H, NH), 7.44 (d, 2H, J = 8.0 Hz, ArH), 7.08 (d, 2H, J
= 8.0 Hz, ArH), 5.78 (s, 2H, NH2), 4.30 (s, 1H, CH), 2.42 (d,
1H, J = 16.8 Hz, CH2), 2.31 (d, 1H, J = 16.8 Hz, CH2), 2.17 (d,
1H, J = 16.0 Hz, CH2), 1.99 (d, 1H, J = 16.0 Hz, CH2), 1.02 (s,
3H, CH3), 0.90 (s, 3H, CH3).
Anal. Calcd. for C18H18BrN3O: C, 58.08; H, 4.87; N, 11.29;
Found C, 58.12; H, 4.88; N, 11.35.
[8] S. J. Tu, C. B. Miao, F. Fang, Y. J. Feng, T. J. Li, Q. Y.
Zhuang, X. J. Zhang, S. L. Zhu and D. Q. Shi, Bioorg. Med. Chem.
Lett., 14, 1533 (2004).
[9a] R. D. Larsen, E. G. Corley, A. O. King, J. D. Carrol, P.
Davis, T. R. Verhoeven, P. J. Reider, M. Labelle, J. Y. Gauthier, Y. B.
Xiang and R. Zamboni, J. Org. Chem., 61, 3398 (1996); [b] Y. L. Chen,
K. C. Fang, J. Y. Sheu, S. L. Hsu and C. C. Tzeng, J. Med. Chem., 44,
2374 (2001); [c] G. Roma, M. D. Braccio, G. Grossi and M. Chia, Eur.
J. Med. Chem., 35, 1021 (2000).
[10] D. Doube, M. Bloun, C. Brideau, C. Chan, S. Desmarais, D.
Eithier, J. P. Falgueyeret, R. W. Friesen, M. Girad, Y. Girad, J. Guay, P.
Tagari and R. N. Yong, Bioorg. Med. Chem. Lett., 8, 1225 (1998).
[11a] M. P. Maguire, K. R. Sheets, K. Mcvety, A. P. Spada and A.
Ziberstein, J. Med. Chem., 37, 2129 (1994); [b] O. Bilker, V. Lindo, M.
Panico, A. E. Etiene, T. Paxton, A. Dell, M. Rogers, R. E. Sinden and H.
R. Morris, Nature, 392, 289 (1998).
[12] S. Margarita, V. Yamila, O. Estael, M. Nazario, M. Roberto,
Q. Margaria, S. Carlos, S. Jose L. N. Hector, B. Norbert, P. Oswald M
and D. Camiel, J. Heterocyclic Chem., 37, 735 (2000).
2-Amino-4-(3',4'-methylenedioxylphenyl)-3-cyano-7,7-dimethyl-
5-oxo-1,4,5,6,7,8-hexahydroquinoline (4k).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3410, 3323 and 3222 (NH
and NH2), 2182 (CN), 1640 (C=O), 1600 (C=C) cm-1; 1H NMR:
ꢀ 8.83 (s, 1H, NH), 6.77-6.58 (m, 3H, ArH), 5.95 (s, 2H,
OCH2O), 5.71 (s, 2H, NH2), 4.25 (s, 1H, CH), 2.40 (d, 1H, J =
16.8 Hz, CH2), 2.32 (d, 1H, J = 16.8 Hz, CH2), 2.17 (d, 1H, J =
16.0 Hz, CH2), 2.01 (d, 1H, J = 16.0 Hz, CH2), 1.02 (s, 3H,
CH3), 0.92 (s, 3H, CH3).
Anal. Calcd. for C19H19N3O3: C, 67.64; H, 5.68; N, 12.46;
Found C, 67.78; H, 5.58; N, 12.34.
2-Amino-4-(4'-methylphenyl)-3-cyano-7,7-dimethyl-5-oxo-1,4,
5,6,7,8-hexahydroquinoline (4l).
[13a] S. J. Tu, F. Fang, C. B. Miao, H. jiang, Y. J. Feng, D. Q. Shi
and X. S. Wang, Tetrahedron Lett., 44, 6153 (2003); [b] S. J. Tu, T. J.
Li, F. Shi, F. Fang, S. L. Zhu, X. Y. Wei and Z. M. Zong, Chem Lett.,
34, 733 (2005).
This compound was obtained according to above general
procedure; ir (potassium bromide): 3392, 3324 and 3223 (NH
and NH2), 2194 (CN), 1662 (C=O), 1601 (C=C) cm-1; 1H NMR:
ꢀ 8.82 (s, 1H, NH), 7.06 (d, 2H, J = 8.0 Hz, ArH), 7.02 (d, 2H, J
= 8.0 Hz, ArH), 5.69 (s, 2H, NH2), 4.26 (s, 1H, CH), 2.42 (d,
1H, J = 16.8 Hz, CH2), 2.28 (d, 1H, J = 16.8 Hz, CH2), 2.23 (s,
3H, CH3), 2.16 (d, 1H, J = 16.0 Hz, CH2), 1.96 (d, 1H, J = 16.0
Hz, CH2), 1.02 (s, 3H, CH3), 0.90 (s, 3H, CH3).
[14a] The crystal data for 4a: C18H20N3O1.5,
Mr =302.37,
Monoclinic P 21/c, a =9.1652 (13) Å, b = 14.716(2) Å, c = 23.596 (3) Å,
V = 3175.1 (7) Å3, Z = 8, T = 193 (2) K , μ = 0.08 mm-1, F(000) =1288,
35240reflections measured, 7266 unique reflections, R = 0.068, wR=
0.143; [b] S. J. Tu, J. P. Zhang, X. T. Zhu, J. N. Xu and Q. Wang, Acta
Cryst., E61, o983 (2005).