F
S. J. Kalita, D. C. Deka
Letter
Synlett
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Reinhoudt, D. N. J. Am. Chem. Soc. 2000, 122, 3617.
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(s, 1 H), 6.41 (d, 1 H, J = 15.9 Hz), 7.19–7.31 (m, 5 H), 11.28 (s, 2
H) ppm. 13C NMR (75 MHz, DMSO-d6): δ = 43.0, 75.0, 121.5,
126.2, 127.7, 128.4, 128.7, 134.3, 136.5, 150.0, 171.6 ppm. IR
(KBr): νmax = 3234, 3030, 2974, 1734, 1680, 1616, 1560 cm–1
.
ESI-MS: m/z calcd for C13H12N2O3+: 244.08; found: 245.0 [M +
H]+. Anal. Calcd (%) for C13H12N2O3: C, 63.93; H, 4.95; N, 11.47.
Found: C, 64.08; H, 5.07; 11.29.
1,3-Dimethyl-5-(thiophen-2-ylmethyl)pyrimidine-
2,4,6(1H,3H,5H)-trione (4cn)
1
(15) (a) Zalukaev, L. P.; Trostyanetskaya, V. L. Chem. Heterocycl.
Compd. 1971, 7, 781; Khim. Geterotsikl. Soedin. 1971, 6, 836.
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Pale yellow solid; 0.226 g (90%); mp 118–119 °C. H NMR (300
MHz, CDCl3): δ = 3.20 (s, 6 H), 3.72 (s, 3 H), 6.76–6.77 (m, 1 H),
6.85–6.88 (m, 1 H), 7.12–7.13 (m, 1 H) ppm. 13C NMR (75 MHz,
CDCl3): δ = 28.4, 30.7, 50.4, 125.2, 127.0, 127.2, 136.4, 151.0,
167.7 ppm. IR (KBr): νmax = 2976, 1672, 1589 cm–1. ESI-MS: m/z
calcd for C11H12N2O3S+: 252.06; found: 253.0 [M + H]+. Anal.
Calcd (%) for C11H12N2O3S: C, 52.37; H, 4.79; N, 11.10. Found: C,
52.22; H, 4.94; 10.98.
(16) Jursic, B. S.; Neumann, D. M. Tetrahedron Lett. 2001, 42, 4103.
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Gilbert, I. H.; González-Pacanowska, D. Eur. J. Med. Chem. 2010,
45, 5140. (b) Vieira, A. A.; Gomes, N. M.; Matheus, M. E.;
Fernandes, P. D.; Figueroa-Villar, J. D. J. Braz. Chem. Soc. 2011,
22, 364. (c) Figuero a Villar, J. D.; Vieira, A.; Marinho, B.; Souza,
L.; Fernandes, P. Med. Chem. Commun. 2015, 6, 1427.
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Lett. 2006, 47, 651. (b) Ramachary, D. B.; Kishor, M.; Reddy, Y. V.
Eur. J. Org. Chem. 2008, 975.
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2012, 16, 291.
1,3-Dimethyl-5-(naphthalen-1-ylmethyl)pyrimidine-
2,4,6(1H,3H,5H)-trione (4cp)
White solid; 0.266 g (90%); mp 153–154 °C. 1H NMR (300 MHz,
CDCl3): δ = 2.92 (s, 6 H), 3.91 (s, 3 H), 7.22 (t, 1 H, J = 6.9 Hz),
7.33 (t, 1 H, J = 7.8 Hz), 7.47–7.53 (m, 2 H), 7.75 (d, 1 H, J = 8.4
Hz), 7.82 (d, 1 H, J = 8.1 Hz), 7.94 (d, 1 H, J = 8.4 Hz) ppm. 13C
NMR (75 MHz, CDCl3): δ = 28.1, 34.7, 50.8, 123.2, 124.9, 125.8,
126.3, 127.7, 128.6, 128.9, 131.4, 131.5, 133.7, 150.9, 168.6
ppm. IR (KBr): νmax = 3953, 1695, 1658, 1560 cm–1. ESI-MS: m/z
calcd for C17H16N2O3+: 296.12; found: 297.1 [M + H]+. Anal. Calcd
(%) for C17H16N2O3: C, 68.91; H, 5.44; N, 9.45. Found: C, 68.76; H,
5.60; N, 9.63.
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2016, 52, 12813.
(24) General Procedure for the Synthesis of 5-Monoalkylbarbitu-
rates 4aa–cp
(25) (a) Kalita, S. J.; Mecadon, H.; Deka, D. C. RSC Adv. 2014, 4, 10402.
(b) Kalita, S. J.; Mecadon, H.; Deka, D. C. RSC Adv. 2014, 4, 32207.
(c) Kalita, S. J.; Mecadon, H.; Deka, D. C. Tetrahedron Lett. 2015,
56, 731. (d) Kalita, S. J.; Saikia, N.; Deka, D. C.; Mecadon, H. Res.
Chem. Intermed. 2016, 42, 6863. (e) Kalita, S. J.; Deka, D. C.;
Mecadon, H. RSC Adv. 2016, 6, 91320. (f) Kalita, S. J.; Bayan, R.;
Devi, J.; Brahma, S.; Mecadon, H.; Deka, D. C. Tetrahedron Lett.
2017, 58, 566. (g) Kalita, S. J.; Das, B.; Deka, D. C. SynOpen 2017, 1,
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(26) Chikashita, H.; Miyazaki, M.; Itoh, K. Synthesis 1984, 308.
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Chem. 2001, 439. (b) Butler, R. N.; Cunningham, W. J.; Coyne, A.
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A mixture of barbituric acid 1 (1 mmol) and aldehyde 2 (1
mmol) was refluxed in 5 mL of water for an appropriate time
until the generation of 5-arylidenebarbituric acid as indicated
by TLC. Next 2-aminothiophenol (3, 1 mmol) and benzaldehyde
(2a, 1 mmol) were added, and the reaction mixture was further
refluxed for an appropriate time. On completion of the reaction
as indicated by TLC the reaction mixture was allowed to cool to
room temperature and was extracted with EtOAc (3 × 10 mL).
After drying with anhydrous Na2SO4 and evaporation under
reduced pressure, the crude product was purified suitably
either by recrystallization from a DCM/EtOH (1:1) solvent
mixture or column chromatography on silica gel using
EtOAc/hexane (2:8) as the eluent to afford 5-monoalkylbarbi-
turate 4.
5-Benzylpyrimidine-2,4,6(1H,3H,5H)-trione (4aa)
White solid; 0.191 g (88%); mp 209–210 °C. 1H NMR (300 MHz,
DMSO-d6): δ = 3.22–3.24 (m, 2 H), 3.87–3.90 (m, 1 H), 7.05–7.24
(m, 5 H), 11.17 (s, 2 H) ppm. 13C NMR (75 MHz, DMSO-d6): δ =
33.3, 49.3, 126.7, 128.3, 128.9, 137.4, 150.6, 170.0 ppm. IR
(KBr): νmax = 3234, 2939, 1716, 1681, 1581 cm–1. ESI-MS: m/z
calcd for C11H10N2O3+: 218.07; found: 219.0 [M + H]+. Anal. Calcd
(%) for C11H10N2O3: C, 60.55; H, 4.62; N, 12.84. Found: C, 60.70;
H, 4.46; N, 13.02.
(29) CCDC 1574477 contains the supplementary crystallographic
data for compound 4cn. The data can be obtained free of charge
from The Cambridge Crystallographic Data Centre via
5-Cinnamyl-6-hydroxypyrimidine-2,4(1H,3H)-dione (4ah)
Pale yellow sticky solid; 0.195 g (80%). 1H NMR (300 MHz,
DMSO-d6): δ = 2.68 (d, 2 H, J = 7.2 Hz), 5.99–6.09 (m, 1 H), 6.27
(30) (a) Zhu, C.; Falck, J. R. ChemCatChem 2011, 3, 1850. (b) Zhu, C.;
Akiyama, T. Synlett 2011, 1251. (c) Zhu, C.; Saito, K.; Yamanaka,
M.; Akiyama, T. Acc. Chem. Res. 2015, 48, 388.
© Georg Thieme Verlag Stuttgart · New York — Synlett 2017, 28, A–F