Month 2017
New Series of 2-Amino-4-aroyl-5-oxo-5,6-dihydro-2H-pyrano[3,2-c]quinoline-3-
carbonitrile
2
1
188, 1673, 1593, 1501, 1390, 1320, 1230, 1160, 1113,
2-Amino-4-(3,4-dimethoxybenzoyl)-5-oxo-5,6-dihydro-4H-
pyrano[3,2-c]quinoline-3-carbonitrile (4h).
yellow powder; mp 280–285°C. υmax (KBr): 3407,
À1
Yield 85%;
023 cm ; δH (300 MHz, DMSO-d ), 11.89 (s, 1H,
6
NH), 8.23 (t, J = 7.2 Hz, 2H, Ar), 7.87 (d, J = 8.1 Hz,
1
7
H, Ar), 7.61 (t, J = 7.8 Hz, 1H, Ar), 7.46 (bs, 2H, NH2),
.40 (d, J = 8.4 Hz, 1H, Ar), 7.36 (t, J = 8.1 Hz, 2H,
3288, 3173, 2832, 2196, 1672, 1629, 1587, 1510,
À1
1
384, 1260, 1161, 1118, 1022 cm
;
δH
(
300 MHz, DMSO-d ), 11.86 (s, 1H, NH), 7.85 (t,
6
Ar), 7.32 (t, J = 7.5 Hz, 1H, Ar), 5.36 (s, 1H, CH); δC
75 MHz, DMSO-d ), 197.8, 167.5, 164.1, 161.1, 160.6,
(
J = 9.0 Hz, 2H, Ar), 7.58 (d, J = 9.0 Hz, 2H, Ar),
.41 (bs, 2H, NH ), 7.28–7.38 (m, 2H, Ar), 7.13 (d,
6
7
1
1
52.6, 138.2, 133.1, 132.5, 132.4, 131.9, 122.7, 121.9,
19.5, 116.4, 116.1, 116.0, 112.2, 107.7, 52.1, 37.6.
Found: %C, 66.63, %H, 3.22, %N, 11.78. C H FN O
2
J = 9.0 Hz, 1H, Ar), 5.31 (s, 1H, CH), 3.88 (s, 3H,
CH ), 3.83 (s, 3H, CH ); δ (75 MHz, DMSO-d ),
97.0, 162.3, 161.1, 160.7, 154.0, 152.7, 148.9, 138.2,
131.8, 128.8, 122.6, 119.7, 116.0, 112.3, 111.6, 111.3,
08.1, 56.2, 55.9, 52.6, 37.2. Found: %C, 65.63, %H,
4.08, %N, 10.56. C H N O requires %C, 65.50,
3
3
C
6
2
0
12
3 3
1
requires %C, 66.48, %H, 3.35, %N, 11.63.
2
-Amino-4-(4-methylbenzoyl)-5-oxo-5,6-dihydro-4H-pyrano
[
3,2-c]quinoline-3-carbonitrile (4e).
Yield 96%; yellow
1
powder; mp 260–262°C. υmax (KBr): 3453, 3300, 3172,
2
2
17
3
5
2
1
8
191, 1668, 1499, 1388, 1315, 1251, 1178, 1113,
%H, 4.25, %N, 10.42.
À1
034 cm ; δ (300 MHz, DMSO-d ), 1.86 (s, 1H, NH),
H
6
.01 (d, J = 7.8 Hz, 2H, Ar), 7.86 (d, J = 9.0 Hz, 1H,
Ar), 7.60 (t, J = 6.0 Hz, 1H, Ar), 7.42 (bs, 2H, NH2),
.29–7.39 (m, 4H, Ar), 5.31 (s, 1H, CH), 2.41 (s, 3H,
CH ); δ (75 MHz, DMSO-d ), 198.5, 161.1, 160.6,
Acknowledgment. We are grateful to the Urmia University for
financial support.
7
3
C
6
1
1
52.6, 144.6, 138.2, 133.7, 131.8, 129.7, 129.6, 122.6,
21.9, 119.6, 116.0, 112.3, 107.9, 52.4, 37.5, 21.6.
REFERENCES AND NOTES
Found: %C, 70.73, %H, 4.18, %N, 11.89. C H N O
requires %C, 70.58, %H, 4.23, %N, 11.76.
2
1
15
3
3
[1] El-Agrody, A.; Abd-Rabboh, H.; Al-Ghamdi, A. Med Chem
Res 2013, 22(3), 1339.
2
-Amino-4-(4-hydroxybenzoyl)-5-oxo-5,6-dihydro-4H-pyrano
[2] Abu-Hashem, A.; Aly, A. Arch Pharm Res 2012, 35(3),
437.
[
3,2-c]quinoline-3-carbonitrile (4f).
Yield 90%; yellow
[3] Hassanin, H.; Ibrahim, M.; Alnamer, Y. Turkish Journal of
powder; mp 295–300°C. υmax (KBr): 3418, 3221, 2194,
Chemistry 2012, 36, 682.
À1
1
678, 1575, 1387, 1322, 1234, 1164, 1116 cm ; δH
[4]
Chen, J.; Chen, P.; Liao, C.; Huang, S.; Chen, I. J Nat Prod
(
300 MHz, DMSO-d ), 11.83 (s, 1H, NH), 10.47 (s, 1H,
2007, 70, 1444.
6
[5] Cairns, H.; Cox, D.; Gould, K.; Ingall, A.; Suschitzky, J. J Med
OH), 8.00 (d, J = 8.4 Hz, 2H, Ar), 7.86 (d, J = 9.0 Hz, 1H,
Ar), 7.59 (t, J = 9.0 Hz, 1H, Ar), 7.37 (bs, 2H, NH2),
Chem 1985, 28(12), 1832.
[6]
Isaka, M.; Tanticharoen, M.; Kongsaeree, P.; Thebtaranonth, Y.
7
.28–7.34 (m, 2H, Ar), 6.89 (d, J = 9.0 Hz, 2H, Ar), 5.25
J Org Chem 2001, 66, 4803.
[7] Koizumi, F.; Fukumitsu, N.; Zhao, J.; Chanklan, R.;
(s, 1H, CH); δ (75 MHz, DMSO-d ), 196.8, 163.0, 161.1,
C
6
Miyakawa, T.; Kawahara, S.; Iwamoto, S.; Suzuki, M.; Kakita, S.;
Rahayu, E.; Hosokawa, S.; Tatsuta, K. J Antibiot 2007, 60, 455.
[8] Chen, I.; Tsai, I.; Teng, C.; Chen, J.; Chang, Y.; Pezzuto, M.
Phytochemistry 1997, 46, 525.
1
60.6, 152.7, 138.2, 132.2, 131.7, 127.6, 122.6, 121.8,
119.6, 115.9, 115.7, 112.3, 108.1, 52.7, 37.0. Found: %C,
6
6
6.98, %H, 3.49, %N, 11.84. C H N O requires %C,
2
0 13 3 4
[9] Hanawa, F.; Fokialakis, N.; Skaltsounis, A. L. Planta Med
6.85, %H, 3.65, %N, 11.69.
2004, 70, 531.
2
-Amino-4-(4-methoxybenzoyl)-5-oxo-5,6-dihydro-4H-pyrano
[10] Rufchahi, M.; Gilani, M. A. G. Dyes Pigm 2012, 95,
[3,2-c]quinoline-3-carbonitrile (4g).
Yield 98%; white
632.
powder; mp 280–284°C. υmax (KBr): 3337, 3185, 2837,
[11] Cioc, R. C.; Ruijter, E.; Orru, R. V. A. Green Chem 2014, 16,
958.
2
2
1
8
7
203, 1674, 1629, 1596, 1382, 1325, 1261, 1171, 1117,
[12] Sarkar, S.; Das, D. K.; Khan, A. T. RSC 2014, 4, 53752.
À1
028 cm ; δ (300 MHz, DMSO-d ), 11.84 (s, 1H, NH),
H
6
[13] Khalafy, J.; Prager, R. H. Aust J Chem 1998, 51, 925.
[14] Molla Ebrahimlo, A. R.; Khalafy, J.; Prager, R. H. Aust. J.
.10 (bd, 2H, J = 6.9 Hz, Ar), 7.86 (d, J = 6.3 Hz, 1H, Ar),
.59 (d, J = 7.0 Hz, 1H, Ar), 7.20–7.50 (m, 4H,
Chem 2009, 62, 126.
15] Rimaz, M.; Khalafy, J.; Moghadam, P. N. Aust. J. Chem 2010
396.
[16] Poursattar Marjani, A.; Khalafy, J.; Salami, F.; Mohammadlou,
M.; Synthesis 2015, 47 (11), 1656.
17] Poursattar Marjani, A.; Khalafy, J.; Salami, F.; Ezzati, M.;
[
NH + 2Ar-H), 7.09 (d, J = 6.9 Hz, 2H, Ar), 5.29 (s, 1H,
2
1
CH), 3.86 (s, 3H, CH ); δ (75 MHz, DMSO-d ), 197.2,
3
C
6
164.0, 161.1, 160.6, 152.6, 138.2, 131.9, 129.0, 122.6,
[
121.9, 119.6, 116.0, 114.4, 112.3, 108.0, 56.0, 52.5, 37.2.
ARKIVOC 2015, v, 277.
[18] Riley, H. A.; Gray, A. R. Organic Syntheses, Wiley & Sons,
New York, NY, Collect. II., 1943, p 509.
Found: %C, 67.73, %H, 3.92, %N, 11.40. C H N O
1 15 3 4
2
requires %C, 67.56, %H, 4.05, %N, 11.25.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet