SYNTHESIS OF 4-ALKYL-2-ARYL-1,3-OXAZOLE[5,4-d]PYRIMIDINE-...
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0.033 mol of sodium hydroxide were added 0.033 mol
of glycine and 0.01 mol of dichloroacrylonitrile I. The
mixture was stirred for 24 h at 20–25°C. When the
solvent was removed in a vacuum to a half volume, the
residue was acidified with hydrochloric acid to pH
~4–5. The precipitate was filtered off, and the com-
pounds ІІІc, IIIg were purified by the recrystal-
lization. The physicochemical constants of compound
ІІІc coincide with the literature data [24].
was added 0.022 mol of the corresponding amine. The
mixture was heated for 4 h and cooled. The precipitate
was filtered off and recrystallized.
REFERENCES
1. Drach, B.S., Sviridov, E.P., Kisilenko, A.A., and Kirsa-
nov, A.V., Zh. Org. Khim., 1973, vol. 9, no. 9, p. 1818.
2. Vinogradova, T.K., Mis’kevich, G.N., and Drach, B.S.,
Zh. Org. Khim., 1980, vol. 16, no. 9, p. 1869.
3. Brovarets, V.S., Pilyo, S.G., Chernega, A.N., Roma-
nenko, E.A., and Drach, B.S., Zh. Obshch. Khim., 1999,
vol. 69, no. 10, p. 1646.
4. Golovchenko, A.V., Pilyo, S.G., Brovarets, V.S.,
Chernega, A.N., and Drach, B.S., Zh. Obshch. Khim.,
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Chernega, A.N., and Drach, B.S., Heteroatom Chem.,
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Chernega, A.N., and Drach, B.S., Zh. Obshch. Khim.,
2005, vol. 75, no. 11, p. 1902.
N-(2-Aryl-4-cyano-1,3-oxazol-5-yl)-β-alanines
(ІІІd, IIIh) were obtained similarly to compounds
ІІІc, IIIg from the enamides Ia or Ib and β-alanine.
The melting point of compound ІІІd corresponds to
the published data [24].
Methyl 5-amino-2-phenyl-1,3-oxazole-4-car-boxy-
late (IVa) was prepared by a known method [8]. Methyl
5-amino-2-(4-methylphenyl)-1,3-oxazole-4-carboxylate
(IVb) was obtained similarly from orthoester ІІb.
5-Alkylamino-2-aryl-1,3-oxazole-4-carbothio-
amides (Va, Vb, Ve, Vf). To a solution of 0.005 mol
of compound IIIa, IIIb, IIIe or IIIf in 10 ml of
pyridine was added 1 ml of triethylamine. The reaction
mixture was saturated with dry hydrogen sulfide for
~1 h and kept for 12 h at 20–25°C. Then 50 ml of
water was added carefully with stirring, the mixture
was acidified with dilute hydrochloric acid (1:1) to pH
~2. The precipitate was filtered off and the target
compounds were purified by the recrystallization.
7. Sviripa, V.M., Gakh, A.A., Brovarets, V.S., Gutov, A.V.,
and Drach, B.S., Synthesis, 2006, no. 20, p. 3462.
8. Shablykin, O.V., Brovarets, V.S., and Drach, B.S., Zh.
Obshch. Khim., 2007, vol. 77, no. 7, p. 1226.
9. Darch, B.S. and Mis’kevich, G.N., Zh. Org. Khim.,
1977, vol. 13, no. 7, p. 1398.
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1971, vol. 8, p. 503.
11. Ohtsuka, Y., Bull. Chem. Soc. Japan, 1970, vol. 43, p. 187.
12. Temple, C., Jr., Smith, B.H., and Montgomery, J.A.,
J. Org. Chem., 1975, vol. 40, p. 3141.
N-(2-Aryl-4-thiocarbamoyl-1,3-oxazol-5-yl)glycine
(Vc, Vg) and N-(2-aryl-4-thiocarbamoyl-1,3-oxazol-
5-yl)-β-alanine (Vd, Vh) were obtained by a known
method [24]. The physicochemical constants cor-
respond to the published data [24].
13. Cabon, G., Gaucher, B., Gegout, A., Heulle, S., and
Masquelin, Th., Chimia, 2003, vol. 57, no. 5, p. 248.
14. Patil, V.D., J. Heterocycl. Chem., 1973, vol. 10, p. 277.
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vol. 18, p. 2242.
Methyl 2-aryl-5-ethoxymethyleneimino-1,3-oxa-
zole-4-carboxylates (VIa, VIb). A solution of 0.015 mol
of aminooxazole IVa or IVb and 0.00001 mol of methyl
4-phenylsulfonic acid in 20 ml of triethyl orthoformate
was heated on a boiling water bath for 8 h. The solvent
was removed in a vacuum, the residue was treated with
hexane, the precipitate was filtered off and recrystallized.
17. Melik-Ogadzanyan, R.G., Khachaturyan, T.A., et al.,
Arm. Khim. Zh., 1981, vol. 34, no. 4, p. 324.
18. Miyasaka, T., Tanaka, H., et al., J. Med. Chem., 1989,
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19. Tanaka, H., Takashima, H., Ubasawa, M., Sekiya, M.,
Nitta, I., Bala, M., Shigeta, S., Walker, R.T., De
Clercq, E., and Miyasaka, T., J. Med. Chem., 1992,
vol. 35, p. 4713.
4-Alkyl-2-aryl-1,3-oxazole[5,4-d]pyrimidine-7(4H)-
thiones (VIIa–VIIh). A solution of 0.002 mol of the
corresponding thioamides Va–Vh in 15 ml of triethyl
orthoformiate was refluxed for 3 h and cooled to 20–
30°C. The precipitate was filtered off, washed with
diethyl ether, and recrystallized.
20. Goslinski, T., Golankiewicz, B., De Clercq, E., and
Balzarini, J., J. Med. Chem., 2002, vol. 45, p. 5052.
21. De Clercq, E., Nature Rev., 2002, vol. 1, p. 13.
22. Amblard, F., Aucagne, V., Guenot, P., Schinazi, R.F.,
and Agrofoglio, L.A., Bioorg. Med. Chem., 2005,
vol. 13, p. 1239.
23. De Clersq, E., Nature Rev. 2006, vol. 5, p. 1015.
24. Shablykin, O.V., Kucharenko, O.P., Iakovenko, I.N.,
Yarmoluk, S.M., and Brovarets, V.S., Ukrainica
Bioorg. Acta, 2008, vol. 6, no. 1, p. 28.
6-Alkyl-2-aryl-1,3-oxazole[5,4-d]pyrimidin-7(6H)-
ones (VIIIa–VIIIe). To a solution of 0.02 mol of
compound VIa or VIb in 50 ml of anhydrous ethanol
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 82 No. 4 2012