4
Helv. Chim. Acta 2016, 99, 1 – 4
(20,60))); 7.26 – 7.32 (m, H–C(2,10)); 7.45 (d, J = 7.5, H–C
(12)); 7.66 (t, J = 7.5, H–C(11)); 8.11 (d, J = 8.0, H–C(1));
8.21 (d, J = 7.5, H–C(9)). 13C-NMR: 56.5; 62.5; 72.1;
114.1; 116.1; 117.3; 120.6; 121.9; 123.9; 125.2; 129.1; 130.9;
131.8; 134.4; 136.5; 146.8; 147.9; 154.3; 154.6; 155.1; 163.9.
Anal. calc. for C23H18BrN3O4 (479.05): C 57.51, H 3.78, N
8.75; found: C 57.68, H 3.86, N 8.61.
13,13a-Dihydro-6-(4-methoxyphenyl)-6H-phthalazino[1,2-
b]quinazoline-5,8-dione (5g). Yield: 0.22 g (60%). Color-
less crystals. M.p. 195 – 197 °C. IR: 3263, 2916, 2834,
1725, 1676, 1599. 1H-NMR: 3.68 (s, MeO); 6.33 (s, 1 H,
CH); 6.52 – 6.71 (m, 5 H, H–C(20,30,50,60), NH); 7.31
(t, J = 7.5, H–C(10)); 7.48 (t, J = 7.5, H–C(3)); 7.56 (t,
J = 7.5, H–C(2)); 7.66 (td, J = 7.5, 1.5, H–C(11)); 7.87
(d, J = 7.5, H–C(12)); 7.98 (d, J = 7.5, H–C(4)); 8.12 (dd,
J = 7.5, 1.0, H–C(1)); 8.23 (d, J = 7.5, H–C(9)). 13C-NMR:
55.5; 73.1; 114.4; 116.0; 120.4; 124.3; 125.3; 126.9; 129.1;
130.4; 132.0; 133.1; 134.3; 137.5; 138.9; 140.7; 154.3; 155.1;
155.2; 165.8. Anal. calc. for C22H17N3O3 (371.13): C 71.15,
H 4.61, N 11.31; found: C 71.32, H 4.48, N 11.50.
[3] M. Mahdavi, K. Pedrood, M. Safavi, M. Saeedi, M. Pordeli, S.
K. Ardestani, S. Emami, M. Adib, A. Foroumadi, A. Shafiee,
Eur. J. Med. Chem. 2015, 95, 492.
[4] F. Esmaeili-Marandi, I. Yavari, M. Saeedi, M. Mahdavi, A. Sha-
fiee, Helv. Chim. Acta 2016, 99, 187.
[5] B. Shafii, M. Saeedi, M. Mahdavi, A. Foroumadi, A. Shafiee,
Synth. Commun. 2014, 44, 215.
[6] S. Farzipour, M. Mahdavi, M. Saeedi, H. Yavari, M. Mirzahek-
mati, N. Ghaemi, A. Foroumadi, A. Shafiee, Synth. Commun.
2014, 44, 48.
[7] M. Mahdavi, M. Asadi, M. Saeedi, M. H. Tehrani, S. S. Mirfa-
zli, A. Shafiee, A. Foroumadi, Synth. Commun. 2013, 43, 293.
[8] M. Asadi, S. Masoomi, S. M. Ebrahimi, M. Mahdavi, M. Saeedi,
P. R. Ranjbar, A. Shafiee, A. Foroumadi, Monatsh. Chem. 2014,
145, 497.
[9] M. Asadi, M. Ebrahimi, M. Mahdavi, M. Saeedi, P. R. Ranjbar,
F. Yazdani, A. Shafiee, A. Foroumadi, Synth. Commun. 2013,
43, 2385.
[10] I. Khan, A. Ibrar, N. Abbas, A. Saeed, Eur. J. Med. Chem.
2014, 76, 193.
[11] A. Kamal, B. V. S. Reddy, B. Sridevi, A. Ravikumar, A. Ven-
kateswarlu, G. Sravanthi, J. P. Sridevi, P. Yogeeswari, D. Sri-
ram, Bioor. Med. Chem. Lett. 2015, 25, 3867.
[12] R. Venkatesh, S. Kasaboina, H. K. Gaikwad, S. Janardhan, R.
Bantu, L. Nagarapu, G. N. Sastry, S. K. Banerjee, Eur. J. Med.
Chem. 2015, 96, 22.
13,13a-Dihydro-3,4-dimethoxy-6-(4-methoxyphenyl)-6H-
phthalazino[1,2-b]quinazoline-5,8-dione (5h). Yield: 0.28 g
(65%). Colorless crystals. M.p. 245 – 247 °C. IR: 3270,
[13] W. Lu, I. A. Baig, H. J. Sun, C. J. Cui, R. Guo, I. P. Jung, D.
Wang, M. Dong, M. Y. Yoon, J. G. Wang, Eur. J. Med. Chem.
2015, 94, 298.
1
3004, 2938, 2835, 1711, 1682. H-NMR: 3.68 (s, MeO); 3.87
(s, MeO); 4.13 (s, MeO); 6.22 (s, 1 H, CH); 6.57 – 6.64 (m,
H–C(20,30,50,60)); 7.00 (br. s, 1 H, NH); 7.26 – 7.32 (m, H–
C(2,10)); 7.53 (d, J = 8.0, H–C(12)); 7.66 (td, J = 8.0, 1.5,
H–C(11)); 8.11 (d, J = 7.5, H–C(1)); 8.22 (d, J = 8.0,
H–C(9)). 13C-NMR: 55.5; 56.5; 62.5; 72.0; 114.4; 116.0;
117.2; 120.5; 122.3; 124.1; 125.2; 126.0; 129.1; 131.3; 131.5;
134.2; 137.3; 142.1; 154.1; 155.1; 155.3; 165.0. Anal. calc.
for C24H21N3O5 (431.15): C 66.81, H 4.91, N 9.74; found:
C 66.62, H 5.14, N 9.86.
[14] S. N. Khattab, N. S. Haiba, A. M. Asal, A. A. Bekhit, A. Amer,
H. M. Abdel-Rahman, A. El-Faham, Bioorg. Med. Chem. 2015,
23, 3574.
[15] S. S. Chauhan, S. Pandey, R. Shivahare, K. Ramalingam, S.
Krishna, P. Vishwakarma, M. I. Siddiqi, S. Gupta, N. Goyalc, P.
M. S. Chauhan, Med. Chem. Commun. 2015, 6, 351.
ꢀ
[16] N. Vila, P. Besada, T. Costas, M. C. Costas-Lago, C. Teran,
Eur. J. Med. Chem. 2015, 97, 462.
[17] a) D. Anand, O. P. S. Patel, R. K. Maurya, R. Kant, P. P.
Yadav, J. Org. Chem. 2015, 80, 12410; b) W. Yang, R. Qiao, J.
Chen, X. Huang, M. Liu, W. Gao, J. Ding, H. Wu, J. Org.
Chem. 2015, 80, 482; c) Y. K. Tailor, S. Khandelwal, H. K. Jain,
M. Kumar, Curr. Org. Synth. 2015, 12, 484; d) S. M. Ibrahim,
M. M. Baraka, O. I. El-Sabbagh, H. Kothayer, Med. Chem. Res.
2013, 22, 1488; e) K. Siva Kumar, P. M. Kumar, V. S. Rao, A.
A. Jafar, C. L. T. Meda, R. Kapavarapu, K. V. L. Parsa, M.
Pal, Org. Biomol. Chem. 2012, 10, 3098.
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Received January 28, 2016
Accepted March 15, 2016
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