A. Z. Halimehjani and S. Airamlounezhad
Vol 000
101.9, 125.7, 127.31, 127.35, 128.4, 128.59, 128.98, 129.2, 129.3,
129.9 (2C), 132.5, 136.7, 137.2, 137.9, 146.7, 159.5; CHN Calcd
for C23H18NS2Cl; C, 67.73; H, 4.41; N, 3.43. Found C, 67.69; H,
4.33; N, 3.47. Table 2, entry 3: IR (KBr) υmax (cmÀ1) 1625,
1595, 1527, 1488, 1090, 964, 763, 697; 1H-NMR (300 MHz,
CDCl3) d (ppm) 4.49 (1H, d, J = 13.5Hz), 4.61 (1H, d,
J = 13.5Hz), 4.85 (1H, d, J = 6.2 Hz), 5.88 (1H, d, J = 6.2 Hz),
7.25–7.41 (12H, m), 7.79 (2H, d, J = 8.2 Hz); 13C-NMR
(300MHz, CDCl3) d (ppm) 35.7, 43.2, 103.1, 125.7, 127.8,
128.2, 128.4, 128.6, 128.8, 129.0, 129.2, 133.9, 136.6, 137.8,
138.9, 146.2, 159.0; Anal. Calcd for C23H18NS2Cl; C, 67.73; H,
4.41; N, 3.43. Found C, 67.77; H, 4.65; N, 3.25. Table 2, entry
4: IR (KBr) υmax (cmÀ1) 1603, 1526, 1509, 1255, 1173, 961,
828; 1H-NMR (300 MHz, CDCl3) d (ppm) 3.80 (3H, s), 4.45
(1H, d, J = 13.5Hz), 4.54 (1H, d, J = 13.5Hz), 4.85 (1H, d,
J = 5.9 Hz), 5.83 (1H, dd, J = 5.9 and 1.2 Hz), 6.88 (2H, d,
J = 7.6 Hz), 7.21–7.37 (9H, m), 7.68 (2H, d, J = 8.6 Hz); 13C-
NMR (300 MHz, CDCl3) d (ppm) 35.7, 43.7, 55.3, 104.5, 114.3,
126.9, 127.7, 128.4(2C), 128.8 (2C), 129.0, 132.1, 134.0, 136.6,
144.8, 159.5, 160.0; Anal. Calcd for C24H20NS2OCl; C, 65.83;
H, 4.57; N, 3.20. Found C, 65.60; H, 4.58; N, 2.99.Table 2,
entry 5: IR (KBr) υmax (cmÀ1) 1602, 1511, 1447, 1243, 1177,
21.1, 34.2, 44.0, 104.0, 118.3, 125.6, 127.5, 128.2, 128.7, 129.3,
132.9, 137.4, 137.9, 138.0, 145.7, 159.0. MS (EI): m/z = 337,
264, 105, 91, 77, 51, 45, 41, 39 (100), 29. Table 2, entry 10:
IR (KBr) υ(cmÀ1) 1635, 1606, 1529, 1508, 1250, 1173, 1031,
1
964, 834, 699; H-NMR (300 MHz, CDCl3) d (ppm) 3.81–3.97
(5H, m), 4.87 (1H, d, J = 5.9 Hz), 5.13–5.33 (2H, m), 5.76 (1H,
d, J = 5.9 Hz), 6.0 (1H, m), 6.92 (2H, d, J = 8.7 Hz), 7.25–7.40
(5H, m), 7.74 (2H, d, J = 8.8Hz); 13C-NMR (300 MHz, CDCl3)
d (ppm) 34.2, 44.3, 55.3, 101.9, 113.9, 118.3, 128.0, 128.4,
128.8 (2C), 129.7, 132.9, 140.5, 145.4, 158.7, 159.8; Anal.
Calcd for C20H19NS2O; C, 67.98; H, 5.38; N, 3.97. Found
C, 67.21; H, 5.93; N, 3.70.
Acknowledgment. We are grateful to the faculty of chemistry of
Tarbiat Moallem University for supporting this work.
REFERENCES AND NOTES
1
[1] (a) Patel, H. S.; Patel, N. P. Orient J Chem 1997, 13, 69. (b)
Ei-Subbagh, H. I.; Abadi, A.; A1-Khawad, I. E.; A1-Rashood, K. A.
Arch Pharm 1999, 332, 19. (c) Ingarsal, N.; Amutha, P.; Nagarajan, S.
J Sulfur Chem 2006, 27, 455. (d) Bozsing, D.; Sohar, P.; Gigler, G.;
Kovacs, G. Eur J Med Chem 1996, 31, 663. (e) Tozkoparan, B.; Aktay, G.;
Yeilada, E. Il Farmaco 2002, 57, 145.
964, 768, 697; H-NMR (CDCl3, 500 MHz) 2.40 (3H, s), 4.55(
1H, d, J = 13.5 Hz), 4.62 (1H, d, J = 13.5Hz), 4.91 (1H, d,
J = 5.8 Hz), 5.92 (1H, d, J = 5.8 Hz), 7.19–7.45 (12H, m), 7.84
(2H, d, J = 7.2 Hz); 13C-NMR (CDCl3, 500 MHz); 21.6, 36.1,
44.6, 104.7, 126.2, 127.8, 128.1, 128.7, 128.8, 129.1, 129.5,
130.1, 137.3, 137.8, 138.5, 138.6, 146.3, 159.9; Anal. Calcd for
C24H21NS2; C, 74.41; H, 5.43; N, 3.62. Found C, 73.98; H,
[2] Barret, G. C.; Kane, V. V.; Lowe, G. J Chem Soc 1964, 783.
[3] Schmidt, R. R. Synthesis 1972, 333.
1
[4] (a) Katritzky, A. R. Advances in Heterocyclic Chemsitry;
Academic Press: London, 1990; Vol 50, 86–151. (b) Mironova, G. A.;
Kuklin, V. N.; Kirillova, Y. N.; Ivin, B. A. Chem Heterocycl Compd
(Engl. Transl.) 1986, 22, 1. (c) Ryabukhin, Y. I.; Korzhavina, O. B.;
Suzdalev, K. F. Adv Heterocycl Chem 1996, 66, 131. (d) Toda, T.;
Karikomi, M.; Yasuda, N. Rev Heteroatom Chem 1997, 16, 119. (e)
Fulop, F.; Bernath, G.; Pihlaja, K. Adv Heterocycl Chem 1997, 69, 349.
(f) Hermecz, I. Adv Heterocycl Chem 1998, 70, 1. (g) Hermecz, I. Adv
Heterocycl Chem 2003, 84, 219. (h) Hermecz, I. Adv Heterocycl Chem
2003, 85, 173.
[5] (a) Toldy, L.; Tot, I.; Rezesti, B.; Sekely, J.; Mankeh, I.;
Polgary, I.; Elekes, I. Hungarian Patent, 576936; Byull. Izobret 1977,
38, 147. (b) Schroth, W.; Hermann, J.; Feustel, C.; Schmidt, S.; Jamil,
K. M. Pharmazie 1977, 32, 461.
[6] Koketsu, M.; Okumura, M.; Ishihara, H. Heteroatom Chem
2002, 13, 377.
[7] (a) Chaturvedi, D.; Ray, S. Tetrahedron Lett 2006, 47, 1307. (b)
Azizi, N.; Aryanasab, F.; Saidi, M. R. Org Lett 2006, 8, 5275. (c) Azizi,
N.; Ebrahimi, F.; Akbari, E.; Aryanasab, F.; Saidi, M. R. Synlett 2007,
2797. (d) Azizi, N.; Aryanasab, F.; Torkiyan, L.; Ziyaei, A.; Saidi, M.
R. J Org Chem 2006, 71, 3634. (e) Ziyaei-Halimehjani, A.; Saidi, M. R.
J Sulfur Chem 2005, 26(2), 1. (g) Ziyaei-Halimehjani, A.; Saidi, M. R.
Can J Chem 2006, 84, 1515. (h) Ziyaei-Halimehjani, A.; Marjani, K.;
Ashouri, A. Green Chem 2010, 12, 1306.
[8] Zimin, M. G.; Kamalov, R. M.; Cherkasov, R. A.; Pudovik, A. N.
Phosphorus Sulfur Silicon 1982, 13, 371.
[9] (a) Braun, J. V. Chem Ber 1902, 35, 3368. (b) Mulder, E. J
Prakt Chem 1868, 103, 178.
5.68; N, 3.58. Table 2, entry 6: H-NMR (300 MHz, CDCl3) d
(ppm) 3.80 (3H, s), 4.47 (1H, d, J = 13.3 Hz), 4.55 (1H, d,
J = 13.5Hz), 4.85 (1H, d, J = 5.9 Hz), 5.86 (1H, d, J = 5.9 Hz),
6.84 (2H, d, J = 8.7 Hz), 7.22–7.39 (10H, m), 7.77 (2H, d,
J = 6.7 Hz); 13C-NMR (300 MHz, CDCl3) d (ppm) 35.6, 43.7,
55.3, 104.2, 114.2, 125.4, 125.6, 127.3, 128.3, 128.4, 128.6,
128.8, 128.9, 132.3, 138.1, 145.8, 159.4, 159.8. MS (EI): m/
z = 267, 135, 121, 105, 91(100), 84, 77, 65, 49, 35. Table 2,
1
entry 7: H-NMR (300MHz, CDCl3) d (ppm) 3.86 (3H, s), 4.48
(1H, d, J = 13.5Hz), 4.57 (1H, d, J = 13.5Hz), 4.89 (1H, d,
J = 5.9 Hz), 5.78 (1H, d, J = 5.9 Hz), 6.91 (2H, d, J = 8.9 Hz),
7.27–7.42 (10H, m), 7.73 (2H, d, J = 8.9 Hz); 13C-NMR
(300MHz, CDCl3) d (ppm) 36.9, 44.3, 55.3, 102.1, 113.8,
126.9, 127.3, 127.6, 127.9, 128.1, 128.6, 128.8, 130.7, 136.8,
140.5, 145.5, 159.1, 159.8. MS (EI): m/z = 280, 135, 121, 105,
1
91(100), 77, 65, 45, 32, 29, 27, 15. Table 2, entry 8: H-NMR
(300MHz, CDCl3) d (ppm) 3.88 (2H, m), 4.88 (1H, d,
J = 5.9 Hz), 5.13–5.32 (2H, m), 5.87 (1H, d, J = 5.9 Hz), 5.98
(1H, m), 7.29–7.43 (8H, m), 7.79 (2H, dd, J = 7.9 and 1.2 Hz).
MS (EI): m/z = 324, 121, 105, 77, 64, 57, 51, 45, 41, 39 (100),
1
32, 27. Table 2, entry 9: H-NMR (300 MHz, CDCl3) d (ppm)
2.36 (3H, s), 3.91–3.98 (2H, m), 4.86 (1H, d, J = 5.9Hz), 5.14–
5.34 (2H, m), 5.87–6.12 (2H, m), 7.14–7.81 (7H, m), 7.81 (2H,
dd, J = 8.2 and 1.2 Hz); 13C-NMR (300 MHz, CDCl3) d (ppm)
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet