690
A. A. Aly, A. A. Hassan, Y. R. Ibrahim, and M. Abdel-Aziz
Vol 46
e): 410 (4.0); ms (EI): m/z 317 [Mþ] (100), 300 (22), 286
(24), 256 (14), 234 (26), 225 (34), 190 (24), 175 (22), 160
(42), 152 (32), 126 (30), 113 (40), 98 (20), 94 (40), 80 (26),
77 (32), 68 (26), 54 (20). Anal. Calcd for C14H11N3O4S
(317.33): C, 52.99; H, 3.49; N, 13.24; S, 10.10. Found: C,
52.78; H, 3.40; N,13.10; S, 10.06.
Ethyl 3-methyl-7-oxo-7H-[1,2,4]triazolo[3,4-b]-[1,3]thia-
zine-5-carboxylate (3e). Pale yellow crystals 0.27 g (56%),
1
mp 170ꢀC (ethanol); H-NMR (400 MHz, CDCl3): dH 6.82 (s,
1 H, H-6), 4.17 (q, 2 H, J ¼ 6.7 Hz, CH2-ester), 2.20 (s, 3 H,
C-3-CH3), 1.21 (t, 3 H, J ¼ 6.7, CH3-ester); 13C-NMR (100.6
MHz, deuterio-chloroform): dC 184.2 (C-7), 166.6 (CO-ester),
158.4 (C-3), 151.2 (C-8a), 132.0 (C-5), 124.2 (CH-6), 59.8
(CH2-ester), 22.2 (C-3-CH3), 24.4 (CH3-ester); IR (KBr): mmax
3078-3000 (w, Ar-CH), 2980-2860 (m, aliph.-CH), 1718 (s,
CO-ester), 1700 (s, CO), 1622 (s, C¼¼N), 1590 (s, C¼¼C)
cmꢁ1; kmax (CH3CN, nm, lg e): 390 (3.2); ms (EI): m/z 239
[Mþ] (100), 194 (24), 166 (24), 151 (18), 126 (22), 113 (56),
80 (16), 64 (16), 54 (18). Anal. Calcd for C9H9N3O3S
(239.25): C, 45.18; H, 3.79; N, 17.56; S, 13.40. Found; C,
45.04; H, 3.70; N, 17.40; S, 13.40.
Ethyl 3-(40-methoxyphenyl)-7-oxo-7H-[1,2,4]triazolo-[3,4-
b][1,3]thiazine-5-carboxylate (3c). Yellow crystals 0.53
g
1
(80%), mp 298ꢀC (acetonitrile); H-NMR (400 MHz, deuterio-
chloroform): dH 7.49-7.28 (m, 4 H, Ar-H), 6.80 (s, 1 H, H-6),
4.10 (q, 2 H, J ¼ 6.9 Hz, CH2-ester), 3.90 (s, 3 H, OCH3),
1.25 (t, 3 H, J ¼ 6.9 Hz, CH3-ester); 13C-NMR (100.6 MHz,
deuterio-chloroform): dC 185.0 (C-7), 165.9 (CO-ester), 158.6
(C-3), 156.0 (CH3O-C), 150.8 (C-8a), 134.2 (Ar-C-10), 131.6
(C-5), 130.2 (meta-Ar CH), 125.2 (CH-6), 123.0 (ortho-Ar
CH), 60.0 (CH2-ester), 58.8 (OCH3), 24.3 (CH3-ester); IR
(KBr): mmax 3060-3007 (w, Ar-CH), 2996-2886 (aliph.-CH),
1722 (s, CO-ester), 1700 (s, CO), 1632 (s, C¼¼N), 1590 (m,
C¼¼C) cmꢁ1; kmax (CH3CN, nm, lg e): 418 (4.1); ms (EI): m/z
331 [Mþ] (100), 316 (18), 300 (22), 286 (32), 258 (28), 226
(34), 205 (16), 174 (40), 126 (34), 113 (42), 108 (32), 99 (20),
80 (24), 77 (26), 68 (26), 54 (24). Anal. Calcd for
C15H13N3O4S (331.35): C, 54.37; H, 3.95; N, 12.68; S, 9.68.
Found: C, 54.30; H, 3.98; N, 12.62; S, 9.72.
REFERENCES AND NOTES
[1] Ryabukhin, Y. I.; Korzhavina, O. B.; Suzdalev, K. F. Adv
Heterocycl Chem 1996, 66, 131.
[2] Coen, S.; Ragonnet, B.; Vieillescazes, C.; Roggero, J.-P.
Heterocycles 1985, 23, 1225.
[3] Yavari, I.; Roberts, J. D. Org Magn Reson 1980, 14, 61.
[4] Mavrova, A. T.; Wesselinova, D.; Tsenov, Y. A.; Denkova,
P. Eur J Med Chem 2009, 44, 63.
Ethyl 3-(40-bromobenzyl)-7-oxo-7H-1,2,4-triazolo[3,4-
b][1,3]thiazine-5-carboxylate (3d). Yellow crystals 0.47 g
(62%), mp 290ꢀC (ethyl acetate). 1H-NMR (400 MHz, deu-
terio-DMSO): dH 7.46-7.10 (m, 4 H, Ar-H), 6.70 (s, 1 H, H-6),
4.07 (s, 2H, benzyl-CH2), 4.14 (q, 2 H, J ¼ 6.9 Hz, CH2-
ester), 1.21 (t, 3 H, J ¼ 6.9, CH3-ester); 13C-NMR (100.6
MHz, deuterio-DMSO): dC 183.2 (C-7), 166.2 (CO-ester),
158.3 (C-3), 150.6 (C-8a), 134.8 (Br-C), 132.0 (C-5), 129.2
(Ar-C-10), 126.8 (ortho-Ar CH), 124.4 (CH-6), 122.2 (meta-Ar
CH), 60.2 (CH2-ester), 33.6 (benzyl-CH2), 24.2 (CH3-ester);
IR (KBr): mmax 3082-3015 (w, Ar-CH), 2980-2880 (m, aliph.-
CH), 1726 (s, CO-ester), 1700 (s, CO), 1612 (br, s, C¼¼N),
1588 (m, C¼¼C), 1112 (m, CAO) cmꢁ1; kmax (CH3CN, lg e,
nm): 388 (4.0); ms (EI): m/z 395 [Mþ1] (94), 393 [M-1]
(100) 313 (32), 268 (28), 240 (26), 224 (45), 212 (28), 172
(40), 170 (55), 126 (18), 113 (24), 98 (30), 80 (22), 77 (40),
68 (22), 80 (22), 54 (18). Anal. Calcd for C15H12BrN3O3S
(394.24): C, 45.70; H, 3.07; Br, 20.27; N, 10.66; S, 8.13.
Found: C, 45.60; H, 3.00; Br, 20.37; N, 10.50; S, 8.20.
[5] Aly, A. A.; Hassan, A. A.; El-Sheref, E. M.; Mohamed, M.
A.; Brown, A. B. J Heterocycl Chem 2008, 45, 521.
[6] Aly, A. A.; Hassan, A. A.; Ameen, A. M.; Brown, A. B.
Tetrahedron Lett 2008, 49, 4060.
[7] Grandolini, G.; Tiralti, M. C.; Rossi, C.; Ambrogi, V.;
Orzalesi, G.; De Regis, M. Farmaco 1987, 42, 43.
[8] Tozkoparan, B.; Aktay, G.; Yesilada, E. Farmaco 2002, 57,
145.
[9] Ram, V. J.; Singha, U. K.; Guru, P. Y. Eur J Med Chem
1990, 25, 533.
[10] Yadav, L.-D. S.; Misra, A. R.; Singh, H. J Agric Food
Chem 1988, 36, 633.
[11] Aly, A. A.; Nour El-Din, A. M.; Gomaa, M. A.-M.; Fahmi,
M. S. Z. Naturforsch 2008, 63B, 223.
[12] Aly, A. A.; El-Shaieb, K. M. J Chem Res 2007, 563.
[13] Aly, A. A.; Hassan, A. A.; Gomaa, M. A.-M.; El-Sheref, E.
M. Arkivoc 2007, xiv, 1.
[14] Varma, R. S. J Indian Chem Soc 1966, 43, 558.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet