M. S. Behalo
Vol 000
General procedures for synthesis of 12–15. A solution
Ethyl-5-oxo-1-(2-(7-(4-phenoxyphenyl)-5-(thiophen-2-yl)-
,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-6-yl)acetyl)-4,5-
2
of acid azide 11 (0.01 mol) in absolute ethanol (20 mL)
was added to a cold solution of active methylene
compounds namely ethyl acetoacetate, ethyl cyanoacetate,
malononitrile, and diethyl malonate in ethanol (20 mL)
containing sodium ethoxide. The reaction mixture was
stirred for 15 h and the solvent was evaporated under
vacuum and poured onto crushed ice. The formed solid
was filtered, dried, and crystallized from proper solvent.
dihydro-1H-1,2,3-triazole-4-carboxylate (15).
Yield: 86%
ꢀ
1
(
dioxane); M.p. 205–7°C. IR spectrum (KBr, ν, cm ):
1
1
735–1673 (3CO); H NMR (DMSO-d ) δ: 8.07–6.96
6
(
m, 12H, Ar─H), 4.85 (s, 1H, methine), 4.13 (q, 2H,
CH CH ), 3.72 (t, 2H, CH ), 3.15 (t, 2H, CH ), 2.83 (s,
2
3
2
2
13
2
1
1
1
H, CH ), 0.98 (t, 3H, CH CH ); C NMR, 174.58,
2 2 3
72.17, 168.26 (3 CO), 157.52, 152.34, 148.60, 132.80,
32.55, 131.20, 128.64, 128.45, 127.60, 126.23, 123.40,
21.70, 121.42, 118.30, 114.32, 112.50 (aromatic
Ethyl-5-methyl-1-(2-(7-(4-phenoxyphenyl)-5-(thiophen-2-yl)-
,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-6-yl)acetyl)-1H-1,2,3-
2
triazole-4-carboxylate (12).
Yield: 84% (benzene); M.p.
carbons), 65.40 (OCH
2
), 44.40, 35.20, 27.85 (3 CH
2
),
ꢀ
1
·+
1
5.36 (CH ); MS: m/z = 587 (M ); Anal. Calcd. for
1
(
(
86–8°C. IR spectrum (KBr, ν, cm ): 1730, 1678
3
1
2CO), 1615 (C═N); H NMR (DMSO-d ) δ: 7.83–6.96
C H N O S (587.67): C, 59.27; H, 4.29; N, 11.92%.
29 25 5 5 2
6
m, 12H, Ar─H), 5.26 (s, 1H, methine), 4.32 (q, 2H,
Found: C, 59.08; H, 4.18; N, 11.83%.
CH CH ), 3.82 (t, 2H, CH ), 3.10 (t, 2H, CH ), 2.95 (s,
2
3
2
2
13
2
H, CH ), 2.35 (s, 3H, CH ), 1.15 (t, 3H, CH CH );
C
2
3
2
3
ACKNOWLEDGMENTS
NMR, 171.35, 167.5 (2 CO), 156.12, 154.35, 150.72,
1
1
36.68, 132.30, 131.22, 128.25, 128.05, 127.50, 127.28,
26.40, 123.36, 122.27, 120.25, 117.20, 115.14, 114.50
The author wishes to thank Benha University and
Ministry of Higher Education and Scientific Research,
Egypt, for the financial support. Antimicrobial evaluation
was performed in Botany Department, Faculty of Science,
Benha University.
(aromatic carbons), 61.25 (OCH ) 48.50, 33.20, 27.75 (3
2
·+
CH ), 15.60, 14.35 (2 CH ); Ms: m/z = 585 (M ); Anal.
Calcd. for C H N O S (585.70): C, 61.52; H, 4.65; N,
2
3
30 27 5 4 2
11.96%. Found: C, 61.37; H, 4.54; N, 11.82%.
Ethyl-5-amino-1-(2-(7-(4-phenoxyphenyl)-5-(thiophen-2-yl)-
,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-6-yl)acetyl)-1H-1,2,3-
2
REFERENCES AND NOTES
triazole-4-carboxylate (13).
Yield: 81% (benzene); M.p.
ꢀ
1
2
1
13–5°C. IR spectrum (KBr, ν, cm ): 3325, 3195 (NH2),
722, 1680 (2CO); H NMR (DMSO-d ) δ: 9.10 (s, 2H,
[1] Liu, X. L.; Feng, T. T.; Wang, D. D.; Liu, H. H.; Yang, C.; Li,
X. N.; Lin, B.; Zhao, Z.; Zhou, Y. Tetrahedron Lett 2016, 57, 4113.
2] Kumar, R. N.; Dev, G. J.; Ravikumar, N.; Swaroop, D. K.;
Debanjan, B.; Bharath, G.; Narsaiah, B.; Jain, S. N.; Rao, A. G. Bioorg
Med Chem Lett 2016, 26, 2927.
3] Tanase, C. I.; Draghici, C.; Cojocaru, A.; Galochkina, A. V.;
Orshanskaya, J. R.; Zarubaev, V. V.; Shova, S.; Enache, C.; Maganu, M.
Bioorg Med Chem 2015, 23, 6346.
1
6
[
NH , exchangeable), 8.78-7.62 (m, 12H, Ar-H), 4.96 (s,
2
1
3
H, methine), 4.34 (q, 2H, CH CH ), 3.61 (t, 2H, CH ),
2 3 2
[
.23 (t, 2H, CH ), 2.98 (s, 2H, CH ), 1.33 (t, 3H,
2
2
13
CH CH ); C NMR, 173.25, 170.30 (2 CO), 153.80,
2
3
1
1
51.65, 147.20, 133.25, 132.37, 131.38, 129.30, 128.45,
27.90, 127.75, 126.40, 123.25, 122.50, 121.36, 118.15,
[4] Sun, C.; Chen, C.; Xu, S.; Wang, J.; Zhu, Y.; Kong, D.; Tao,
H.; Jin, M.; Zheng, P.; Zhu, W. Bioorg Med Chem 2016, 24, 3862.
[
5] Tan, Q.; Zhang, Z.; Hui, J.; Zhao, Y.; Zhu, L. Bioorg Med
Chem 2014, 22, 358.
[6] Haleel, A.; Mahendiran, D.; Veena, V.; Sakthivel, N.;
Rahiman, A. K. Materials Sci Eng C 2016, 68, 366.
7] Quiroga, J.; Romo, P. E.; Ortiz, A.; Isaza, J. H.; Insuasty, B.;
115.60, 114.10 (aromatic carbons), 63.50 (OCH ) 45.25,
2
·+
32.30, 28.68 (3 CH ), 15.20 (CH ); MS: m/z = 586 (M );
2 3
Anal. Calcd. for C H N O S (586.69): C, 59.37; H,
2
9 26 6 4 2
[
4.47; N, 14.32%. Found: C, 59.45; H, 4.51; N, 14.40%.
Abonia, R.; Nogueras, M.; Cobo, J. J Mol Str 2016, 1120, 294.
[8] Barakat, A.; Islam, M. S.; Al-Majid, A. M.; Ghabbour, H. A.;
Yousuf, S.; Ashraf, M.; Shaikh, N. N.; Choudhary, M. I.; Khalil, R.; Ul-
Haq, Z. Bioorg Chem 2016, 68, 72.
5
-Amino-1-(2-(7-(4-phenoxyphenyl)-5-(thiophen-2-yl)-2,3-
dihydro-5H-thiazolo[3,2-a]pyrimidin-6-yl)acetyl)-1H-1,2,3-
triazole-4-carbonitrile (14). Yield: 83% (benzene); M.p.
[9] Zhang, J.; Peng, J.; Wang, T.; Wang, P.; Zhang, Z. J Mol Str
ꢀ
1
224–6°C. IR spectrum (KBr, ν, cm ): 3335, 3250
2016, 1120, 228.
1
(
NH ), 2216 (C≡N), 1677 (CO); H NMR (DMSO-d )
[10] Aksinenko, A. Y.; Goreva, T. V.; Epishina, T. A.; Trepalin, S.
V.; Sokolov, V. B. J Fluorine Chem 2016, 188, 191.
2
6
δ: 7.56-6.99 (m, 12H, Ar─H), 6.50 (s, 2H, NH2,
[11] Saikia, L.; Roudragouda, P.; Thakur, A. J. Bioorg Med Chem
exchangeable), 4.85 (s, 1H, methine), 3.18 (t, 2H, CH ),
2
Lett 2016, 26, 992.
[12] Maddila, S.; Gorle, S.; Seshadri, N.; Lavanya, P.;
Jonnalagadda, S. B. Arabian J Chem 2016, 9, 681.
1
3
2.91 (t, 2H, CH ), 2.40 (s, 2H, CH ); C NMR, 169.50
2 2
(CO), 155.30, 152.25, 148.12, 133.26, 131.60, 131.42,
[
13] Suresh, L.; Kumar, P. S.; Poornachandra, Y.; Kumar, C. G.;
Babu, N. J.; Chandramouli, G. V. Bioorg Med Chem 2016, 24, 3808.
14] Behalo, M. S. Phosphorus, Sulfur and Silicon and the Related
1
1
29.30, 128.20, 127.40, 127.25, 123.50, 123.22, 122.75,
21.50, 118.10, 117.50, 115.37, 114.45 (aromatic
[
carbons and C≡N), 47.25, 36.50, 27.30 (3 CH ); MS:
Elements 2009, 184, 206.
[15] Zhao, M.; Ren, H.; Chang, J.; Zhang, D.; Yang, Y.; He, Y.; Qi,
C.; Zhang, H. Eur J Med Chem 2016, 25, 183.
2
·
+
m/z = 539 (M ); Anal. Calcd. for C H N O S
2
7 21 7 2 2
(539.63): C, 60.10; H, 3.92; N, 18.17%. Found: C,
[16] Hou, J.; Wan, S.; Wang, G.; Zhang, T.; Li, Z.; Tian, Y.; Yu, Y.;
59.92; H, 3.80; N, 18.09%.
Wu, X.; Zhang, J. Eur. J Med Chem 2016, 118, 276.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet