b
was obtained in 91% yield; mp 260°C
5-(3-Benzo[ ]thienyl)hexahydropyrimidine-2,4,6-trione (2b)
(acetic acid). 1H NMR spectrum, δ, ppm: 5.50 (1H, s, 5-H); 7.30-8.00 (5H, m, H arom); 10.90 (2H, br. s, NH);
11.51 (1H, br. s, OH enol). Found, %: C 55.61; H 3.24; N 10.60, S 12.40. C12H8N2O3S. Calculated, %: C 55.38;
H 3.10; N 10.76; S 12.32.
b
was obtained in 91% yield;
5-(Benzo[ ]selenophene-3-yl)hexahydropyrimidine-2,4,6-trione (2c)
1
mp 157-158°C (acetic acid). H NMR spectrum, δ, ppm: 5.37 (1H, s, 5-H); 7.20-7.56 (3H, 5-, 6-, 7-H arom);
7.90 (1H, s, 2-H); 8.00 (1H, m, 4-H); 10.83 (2H, br. s, NH); 11.45 (1H, br. s, OH enol). Found, %: C 46.75;
H 2.35; N 9.35; Se 25.54. C12H8N2O3Se. Calculated, %: C 46.92; H 2.63; N 9.12; Se 25.71.
b
was obtained in 68% yield; mp 89°C (heptane) (mp 89°C [6]).
Benzo[ ]furan-3-acetic Acid (1a)
Found, %: C 68.36; H 4.42. C10H8O3. Calculated, %: C 68.18; H 4.58.
was obtained in 66% yield; mp 108-109°C (heptane)
b
Benzo[ ]thiophene-3-acetic Acid (b)
(mp 108-109°C [7]). Found, %: C 62.23; H 4.27; S 16.53. C10H8O2S. Calculated, %: C 62.48; H 4.19; S 16.68.
was obtained in 58% yield; mp 149-150°C (cyclohexane)
b
Benzo[ ]selenophene-3-acetic Acid (1c)
1
(mp 150°C [3]). H NMR spectrum (DMSO-d6), δ, ppm, (J, Hz): 3.73 (2H, s, CH2); 7.28 (1H, t, J = 7.3, 6-H);
7.38 (1H, t, J = 7.7, 5-H); 7.72 (1H, d, J = 7.7, 4-H); 7.90 (1H, s, 2-H); 7.94 (1H, d, J = 7.3, 7-H); 12.18 (1H,
br. s, CO2H). Found, %: C 50.41; H 3.11; Se 33.28. C10H8O2Se. Calculated, %: C 50.23; H 3.37; Se 33.02.
REFERENCES
1.
2.
3.
4.
M. Hofinger, T. Thorpe, B. Mrreille, and T. Gaspar, Acta Physiol. Plant, 2, No. 4, 275 (1980).
T. Gaspar, Acros Org. Acta, 1, No. 2, 65 (1995); Chem. Abstr., 123, 308548 (1995).
L. Laitem and L. Critiaens, Bull. Soc. Chim. France, 2294 (1975).
S. V. Tolkunov, A. I. Khizhan, S. I. Simonova, N. S. Semenov, and S. N. Lyashchuk, Khim. Geterotsikl.
Soedin., 321 (1994).
5.
V. S. Velezheva, V. P. Sevodin, Yu. V. Erofeev, N. K. Genkina, T. A. Kozik, V. V. Vampilova, and
N. N. Suvorov, Khim. Geterotsikl. Soedin., 360 (1977).
R. Deeshpande and M. V. Paradkar, Synth. Commun., 20, 809 (1990).
O. Dann and M. Kokorudz, Chem. Ber., 91, 172 (1958).
6.
7.
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