690
G. Venkat Reddy, A. Chandra Shekhar, A. Ravi Kumar, G. Sathaiah, B. Narsaiah,
and P. Shanthan Rao
Vol 49
distilled. The final residue was purified by passing through a
column of silica gel to give the corresponding ethylated
products, respectively.
CH2), 5.6 (1H, s, NH), 8.0 (1H, d, ArH), 8.6 (1H, s, ArH), 10.0
(1H, br, NH); Mass (FAB): 387 (M + 1, 42%), 356 (M-NHCH3,
100%), 328 (M-CONHCH3, 62%); Anal. Calcd. for C21H27FN4O2:
C, 65.26; H, 7.04; N, 14.49. Found: C, 65.20; H, 7.12; N, 14.62.
3-Methyl-4-fluoro-6-oxo-6, 9-dihydro-9-ethyl-1H-spiro
[imidazoline (4,5-h) quinoline-2, 10-cyclooctane]-7-N-methyl
carboxamide (3f). Yield 70%; mp: > 300ꢀC; IR (KBr): 3193
9-Ethyl-4-fluoro-N, 2,3-trimethyl-6-oxo-6, 9-dihydro-3H-
imidazo [4,5-h] quinoline-7-carboxamide (3a).
Yield 70%;
mp: > 300ꢀC; IR (KBr): 3185 (NH), 1644 (CO), 1608 (amide
1
CO) cmꢁ1; H-NMR (dueterated chloroform): d 1.5 (3H, t, CH3),
1
2.9 (3H, s, CH3), 3.0 (3H, d, CH3), 4.0 (3H, s, CH3), 4.8 (2H, q,
CH2), 8.0 (1H, d, ArH), 8.7 (1H, s, ArH), 10.0 (1H, br, NH);
Mass (FAB): 317 (M + 1, 45%), 286 (M-NHCH3, 100%), 258
(M-CONHCH3, 58%); Anal. Calcd. for C16H17FN4O2.: C, 60.75;
H, 5.42; N, 17.71. Found: C, 60.70; H, 5.20; N, 17.62.
(NH), 1659 (CO), 1620 (amide CO) cmꢁ1; H-NMR (dueterated
chloroform): d 1.3–1.5 (6H, m, CH3), 2.8 (4H, m, CH2), 2.2–1.8
(10H, m, CH2), 3.0 (3H, d, CH3) 3.8 (3H, s, CH3), 5.1 (2H, q,
CH2), 5.7 (1H, s, NH), 8.0 (1H, d, ArH), 8.7 (1H, s, ArH), 10.0
(1H, br, NH); Mass (FAB): 401 (M + 1, 46%), 370 (M-NHCH3,
100%), 342 (M-CONHCH3, 64%); Anal. Calcd. for C22H29FN4O2:
C, 65.97; H, 7.29; N, 13.98. Found: C, 65.90; H, 7.24; N, 13.92.
9-Diethyl-4-fluoro-N, 3-dimethyl-6-oxo-2-(trifluoromethyl)-
6, 9-dihydro-3H-imidazo [4,5-h] quinoline-7-carboxamide
2,9-Diethyl-4-fluoro-N,3-dimethyl-6-oxo-6,9-dihydro-3H-
imidazo[4,5-h]quinoline-7-carboxamide (3b). Yield 81%; mp:
> 281ꢀC; IR (KBr): 3193 (NH), 1650 (CO), 1596 (amide CO)
cmꢁ1 1H-NMR (dueterated chloroform): d 1.5 (6H, m, 2CH3),
;
2.9 (2H, t, CH2), 3.0 (3H, d, CH3), 4.0 (3H, s, CH3), 5.0 (2H, q,
CH2), 8.0 (1H, d, ArH), 8.7 (1H, s, ArH), 10.0 (1H, br, NH);
Mass (FAB): 331 (M + 1, 44%), 300 (M-NHCH3, 100%), 272
(M-CONHCH3, 62%); Anal. Calcd. for C17H19FN4O2: C, 61.81;
H, 5.80; N, 16.96. Found: C, 61.70; H, 5.72; N, 16.82.
(3g).
Yield 81%; mp: 275ꢀC; IR (KBr): 3240 (NH), 1656
1
(CO), 1612 (amide CO) cmꢁ1; H-NMR (dueterated chloroform):
d 1.6 (3H, t, CH3), 3.1 (3H, d, CH3), 4.3 (3H, s, CH3), 5.1 (2H,
q, CH2), 8.2 (1H, d, ArH), 8.7 (1H, s, ArH), 9.9 (1H, br, NH);
Mass (FAB) 371 (M + 1, 48%), 340 (M-NHCH3, 100%), 312
(M-CONHCH3, 60%); Anal. Calcd. for C16H14F4N4O2: C, 51.89;
H, 3.81; N, 15.13. Found: C, 51.80; H, 3.72; N, 15.12.
3-Methyl-4-fluoro-6-oxo-6,
[imidazoline (4,5-h) quinoline-2, 10-cyclopentane]-7-N-methyl
carboxamide (3c).
Yield 70%; mp > 300ꢀC; IR (KBr):
3269 (NH), 1709 (CO), 1630 (amide CO) cmꢁ1 1H-NMR
9-dihydro-9-ethyl-1H-spiro
;
Acknowledgment. The authors thank Dr. J. S. Yadav, Director,
IICT, for constant encouragement and support.
(dueteratedcholoroform): d 1.5 (6H, m, 2CH3), 1.9–2.4 (8H, m,
CH2), 3.0 (3H, d, CH3), 4.1 (3H, s, CH3), 5.1 (2H, q, CH2), 5.7
(1H, s, NH), 8.1 (1H, d, ArH), 8.7 (1H, s, ArH), 10.0 (1H, br,
NH); Mass (FAB): 359 (M + 1, 41%), 328 (M-NHCH3, 100%),
300 (M-CONHCH3, 62%); Anal. Calcd. for C19H23FN4O2: C,
63.67; H, 6.47; N, 15.63. Found: C, 63.60; H, 6.44; N, 15.62.
3-Methyl-4-fluoro-6-oxo-6, 9-dihydro-9-ethyl-1H-spiro
[imidazoline (4,5-h) quinoline-2, 10-cyclohexane]-7-N-methyl
REFERENCES AND NOTES
[1] Koga, H.; Itoh, A.; Murayama, S.; Suzue, S.; Irikura, T. J Med
Chem 1980, 23, 1358.
[2] Sato, K.; Matsuura, Y.; Inoue, M.; Une, T.; Osada, Y.; Ogawa,
H.; Mitsushi, T. Antimicrob Agents Chemother 1982, 22, 548.
[3] Wise, R.; Andrwes, J.M.; Edwards, L.J. Antimicrob Agents
Chemother 1983, 23, 559.
carboxamide (3d).
3283 (NH), 1659 (CO), 1620 (amide CO) cmꢁ1
Yield 80%; mp: > 300ꢀC; IR (KBr):
1H-NMR
;
(dueterated chloroform): d 1.5 (6H, m, CH3), 2.8–2.2 (10H, m,
CH2), 3.0 (3H, d, CH3), 4.0 (3H, s, CH3), 5.0 (2H, q, CH2), 5.7
(1H, s, NH), 8.0 (1H, d, ArH), 8.7 (1H, s, ArH), 10.1 (1H, br,
NH); Mass (FAB): 373 (M + 1, 40%), 342 (M-NHCH3, 100%),
314 (M-CONHCH3, 60%); Anal. Calcd. for C20H25FN4O2: C,
64.49; H, 6.76; N, 15.04, Found: C, 64.44; H, 6.73; N, 15.10.
3-Methyl-4-fluoro-6-oxo-6, 9-dihydro-9-ethyl-1H-spiro
[imidazoline (4,5-h) quinoline-2, 10-cycloheptane]-7-N-methyl
carboxamide (3e). Yield 75%; mp: > 300ꢀC; IR (KBr): 3263
[4] Von Meel, J. C. A. Arzenium Forsch 1985, 35, 284.
[5] Denny, W.A.; Rewcastle, G. W.; Baguley, B. C. J Med Chem
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[6] Hayakawa, I.; Hiramistu, T.; Tanaka, Y. Chem Pharm Bull
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[7] Chu, D. T. W. J Heterocycl Chem 1990, 27, 839.
[8] Venkat Reddy, G.; Ravikanth, S.; Maitraie, D.; Narsaiah, B.;
Shnathan Rao, P.; Harakishore, K.; Murthy, U. S. N.; Ravi, B.; Ashok
Kumar, B.; Parthasarathy, T. Eur J Med Chem 2009, 44, 1570.
[9] Shanthan Rao, P.; Venkataratnam, R.V. Indian J Chem 1992,
31B, 733.
1
(NH), 1660 (CO), 1620 (amide CO) cmꢁ1; H-NMR (dueterated
chloroform): d 1.5 (6H, m, CH3), 2.8 (4H, m, CH2), 2.2–1.9
(8H, m, CH2), 3.0 (1H, d, CH3), 4.1 (3H, s, CH3), 5.0 (2H, q,
[10] Srinivas, K.; Shanthan Rao, P.; Narsaiah, B.; Madhusudhana
Rao, J. Indian J Chem 2001, 40B, 191.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet