126.28, 124.49, 119.63, 116.93, 112.20. IR (KBr), ν, cm–1: 3424,
2925, 1659, 1626, 1588, 1480, 1298, 1250, 1159. Found, %: С,
62.31; Н, 3.12; N, 16.21. С18H10N4O2S. Calcd %: C, 62.42; H,
2.91; N, 16.18.
17. Khalafy, J.; Molla Ebrahimlo, A. R.; Eisavi, R.; Akbari
Dilmaghani, K. ARKIVOC, 2005, (xiv), 59.
18. Khalafy, J.; Poursattar Marjani, A.; Molla Ebrahimlo, A. R. J.
Braz. Chem. Soc. 2006, 17, 570.
19. Khalafy, J.; Molla Ebrahimlo, A. R. ARKIVOC 2008, (xiii), 65.
20. Ebrahimlo, A. R.; Khalafy, J.; Prager, R. H. Aust. J. Chem. 2009,
62, 126.
10-(Furan-2-yl)-5H-naphtho[1,2-e][1,2,4]triazolo[3,4-
b][1,3,4]thiadiazin-5-one (4e)
21. Molla Ebrahimlo, A. R.; Khalafy, J.; Poursattar Marjani, A.;
Prager, R. H. ARKIVOC 2009, (xii), 17.
o
1
Orange solid, 56%, mp 244 C, H NMR (300 MHz, DMSO-
d6), δ, ppm (J, Hz): 8.52 (1H, d, J = 7.8, Ar); 8.12 (1H, d, J = 7.5,
Ar ); 8.07 (1H, s, Ar); 7.94 (1H, t, J = 7.8, Ar); 7.86 (1H, t , J =
7.5, Ar); 7.50 (1H, d, J = 3.3, Ar); 7.25 (1H, br s, Ar); 6.85 (1H,
dd, J1 = 3.3, J2 = 1.5, Ar). 13C NMR (75 MHz, DMSO-d6), δ,
ppm (J, Hz): 180.33, 146.31, 145.4, 141.07, 139.95, 137.23,
133.90, 132.86, 132.22, 131.96, 131.15, 126.50, 126.38, 125.03,
114.64, 112.93. IR (KBr), ν, cm–1: 2923, 1642, 1622, 1550, 1453,
1308, 771. Found, %: С, 60.11; Н, 2.40; N, 17.52. С16H8N4O2S.
Calcd %: C 59.99; H, 2.52; N, 17.49.
22. Poursattar Marjani, A.; Khalafy, J. Chem. Heterocycl. Compd.
2011, 47, 96.
23. Poursattar Marjani, A.; Khalafy, J.; Molla Ebrahimlo, A. R.;
Prager, R. H. Bull. Korean Chem. Soc. 2011, 32, 2183.
24. Poursattar Marjani, A.; Khalafy, J.; Molla Ebrahimlo, A. R. Synth.
Commun. 2011, 41, 2475.
25. Poursattar Marjani, A.; Khalafy, J.; Prager, R. H. Chem.
Heterocycl. Compd. 2012, 48, 931.
26. Khalafy, J.; Etivand, N.; Dilmaghani, S.; Ezzati, M.; Poursattar
Marjani, A., Tetrahedron Lett., 2014, 55, 3781.
27. Khalafy, J.; Poursattar Marjani, A.; Salami, F. Tetrahedron Lett.
2014, 55, 6671.
28. Khalafy, J.; Ghezelbash, Z. D.; Mahmoody, M. Chem. Heterocycl.
Compd. 2010, 46, 613.
29. Khan, S. I.; Badshah, A.; Chaudhry, A. H.; Aslam, M.; Akhtar, M.
S.; Ashfaq, K. M.; Malik, T. A. Med. Chem. Drug Discov. 2012,
3, 116.
10-Methyl-5H-naphtho[1,2-e][1,2,4]triazolo[3,4-
b][1,3,4]thiadiazin-5-one (4f)
1
Orange solid, 67%, mp 248 oC, H NMR (300 MHz, CDCl3),
δ, ppm (J, Hz): 8.53 (1H, d, J = 7.2, Ar); 8.23 (1H, d, J = 6.9,
Ar); 7.80-7.76 (2H, m, Ar); 6.85 (1H, s, Ar); 2.78 (3H, s, CH3).
13C NMR (75 MHz, CDCl3), δ, ppm (J, Hz): 179.97, 151.66,
140.19, 135.17, 132.99, 132.36, 131.62, 131.17, 130.75, 126.70,
126.54, 124.32. IR (KBr), ν, cm–1: 2923, 2854, 1641, 1594, 1548,
1459, 1357, 1307, 1131, 779. Found, %: С, 58.36; Н, 2.93; N,
20.94. С13H8N4OS. Calcd %: C, 58.20; H, 3.01; N, 20.88.
Acknowledgments
The authors gratefully acknowledge the financial assistance
from Urmia University.
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