Synthesis of New Quinoline Derivatives

Synthesis of New Quinoline Derivatives 3587
(q), 127.4 (CH), 124.1 (CH), 87.4 (CH 2 ), 73.4 (CH), 59.3 (CH 2 ), 58.4 (CH 2 ),
17.6 (CH 3 ); IR (neat, cm 21 ): 3063, 2925, 2876, 1701, 1592, 1479, 1454, 1327,
1053, 997; HRMS (E.I) [M] þ calcd. for C 20 H 18 C1 2 N 2 O ¼ 372.07961; found
372.0811.
5-(8-Methyl-2-chloro-3-quinolyl)-3-methyl-1,3-oxazolone (3g): pale yellow
oil.
1 H NMR (500 MHz, CDCl 3 ): 8.31 (s, 1H, qui-H-4), 7.65 (d, 1H,
J ¼ 8.1 Hz, qui-H-5), 7.52 (d, 1H, J ¼ 8.1 Hz, qui-H-7), 7.42 (t, 1H, J ¼
8.1 Hz, qui-H-6), 5.36 (t, 1H, J ¼ 6.7 Hz, H-5), 4.65 (d, 1H, J ¼ 5.0 Hz,
H-2), 4.53 (d, 1H, J ¼ 5.1 Hz, H-2), 3.63 (dd, 1H, J ¼ 6.7 and 11.5 Hz,
H-4), 2.85 (dd, 1H, J ¼ 6.7 and 11.5 Hz, H-4), 2.75 (s, 3H, CH 3 ), 2.53
(s, 3H, NCH 3 ); 13 C NMR (125 MHz, CDCl 3 ): 147.1 (q), 146.1 (q), 136.2
(CH), 134.6 (q), 134.1 (q), 130.0 (CH), 127.3 (CH), 126.7 (q), 125.5 (CH),
89.3 (CH 2 ), 73.5 (CH), 61.4 (CH 2 ), 41.6 (CH 3 ), 17.7 (CH 3 ); IR (neat,
cm 21 ): 3010, 2952, 2860, 2806, 1653, 1599, 1576, 1485,1463, 1395, 1377,
1363, 1323, 1206, 1170, 1122, 1088, 1060, 1044, 1009; HRMS (E.I)
[M] þ calcd. for C 14 H 15 C1 N 2 O ¼ 262.08729; found 262.0879.
5-(8-Methyl-2-chloro-3-quinolyl)-3-benzyl-1,3-oxazolone (3h): pale yellow
oil.
1 H NMR (500 MHz, CDCl 3 ): 8.32 (s, 1H, qui-H-4), 7.66 (d, 1H,
J ¼ 7.2 Hz, qui-H-5), 7.51 (d, 1H, J ¼ 7.2 Hz, qui-H-7), 7.42 (t, 1H,
J ¼ 7.2 Hz, qui-H-6), 7.34–7.22 (m, 5H, Ph), 5.36 (t, 1H, J ¼ 6.7 Hz, H-5),
4.67 (d, 1H, J ¼ 5.5 Hz, H-2), 4.63 (d, 1H, J ¼ 5.5 Hz, H-2), 3.82 (s, 2H,
NCH 2 ), 3.74 (dd, 1H, J ¼ 7.2 and 11.8 Hz, H-4), 2.86 (dd, 1H, J ¼ 7.2 and
11.8 Hz, H-4), 2.74 (s, 3H, CH 3 ); 13 C NMR (125 MHz, CDCl 3 ): 147.1 (q),
146.1 (q), 138.3 (q), 136.3 (q), 134.6 (CH), 134.1 (q), 130.1 (CH), 128.6
(2 CH), 128.4 (2 CH), 128.4 (q), 127.3 (CH), 126.8 (CH), 125.5 (CH),
87.3 (CH 2 ), 73.5 (CH), 59.4 (CH 2 ), 58.4 (CH 2 ), 19.0 (CH 3 ); IR (neat,
cm 21 ): 3062, 2876, 1641, 1597, 1495, 1454, 1326, 1075, 905; HRMS (E.I)
[M] þ calcd. for C 20 H 19 C1 N 2 O ¼ 338.11859; found 338.1197.
ACKNOWLEDGMENTS
This work was financially supported by the National Fund for Science and
Research, Hungary (OTKA Project No. T 046196). N. M. thanks the
Hungarian Academy of Sciences for a Bolyai J. Fellowship. A grant from
the József Varga Foundation provided to J. T. is gratefully appreciated.
REFERENCES
1. (a) Michael, J. P. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep.
2004, 650–668; (b) Michael, J. P. Quinoline, quinazoline and acridone
alkaloids. Nat. Prod. Rep. 2003, 476–493.