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Torok et al.:
combined chloroform extracts are dried with magnesium sulfate and the solid residue remaining after
removal of solvents is crystallized.
2-Phenylimino-4-oxo-1,3-thiazaspiro[5.5]undecane (IIIa), yield 83%, m.p. 155 °C (ethanol). IR
spectrum (CHCl3): 3 356 (NH). 1H NMR spectrum (CDCl3): 1.50 m, 10 H (C6H10); 2.82 s, 2 H
(CH2−CO); 7.12 m, 5 H (C6H5); 8.32 s, 1 H (NH). 13C NMR spectrum (CDCl3): 169.84, 150.47,
147,03, 128.93, 124.34, 121.61, 48.38, 46.92, 37.59, 25.20, 22.02. For C15H18N2OS (274.3) calcu-
lated: 65.66% C, 6.61% H, 10.21% N; found: 65.52% C, 6.53% H, 10.17% N.
2-(4-Nitrophenylimino)-4-oxo-1,3-thiazaspiro[5.5]undecane (IIIb), yield 59%, m.p. 199 – 202 °C
(ethanol). 1H NMR spectrum (CDCl3): 1.53 m, 10 H (C6H10); 2.83 s, 2 H CH2−CO); 7.60 m, 4 H
(C6H4). 13C NMR spectrum (CDCl3): 169.72, 153.05, 152.12, 144.38, 124.92, 122.24, 49.34, 46.74,
37.41, 24.93, 21.88. For C15H17N3O3S (319.4) calculated: 56.41% C, 5.37% H, 13.16% N; found:
56.37% C, 5.32% H, 13.12% N.
2-(4-Bromophenylimino)-4-oxo-1,3-thiazaspiro[5.5]undecane(IIIc), yield 77%, m.p. 210 °C (ethanol).
1H NMR spectrum (CDCl3): 1.60 m, 10 H (C6H10); 2.80 s, 2 H (CH2−CO); 7.12 m, 4 H (C6H4). 13C
NMR spectrum (CDCl3): 169.80, 151.51, 145.99, 132.06, 123.55, 117.62, 48.75, 46.92, 37.59, 25.16,
22.02. For C15H17BrN2OS (353.3) calculated: 51.00% C, 4.85% H, 7.93% N; found: 50.95% C,
4.80% H, 7.91% N.
2-(4-Methylphenylimino)-4-oxo-1,3-thiazaspiro[5.5]undecane (IIId), yield 76%, m.p. 155 – 156 °C
1
(ethanol). H NMR spectrum (CDCl3): 1.52 m, 10 H (C6H10); 2.31 s, 3 H (CH3); 2.80 s, 2 H (CH2−
CO); 6.90 m, 4 H (C6H4). 13C NMR spectrum (CDCl3): 169.77, 150.67, 144.11, 133.91, 129.50,
121.43, 48.30, 46.77, 37.44, 25.07, 21.89, 20.94. For C18H20N2OS (312.4) calculated: 69.20% C,
6.45% H, 8.97% N; found: 69.17% C, 6.42% H, 8.93% N.
2-(4-Methoxyphenylimino)-4-oxo-1,3-thiazaspiro[5.5]undecane(IIIe), yield 65%, m.p. 132 – 133 °C
(ethanol). 1H NMR spectrum (CDCl3): 1.52 m, 10 H (C6H10); 2.80 s, 2 H (CH2−CO); 3.77 s, 3 H
(OCH3); 6.86 m, 4 H (C6H4); 8.30 s, 1 H (NH). 13C NMR spectrum (CDCl3): 169.80, 156.56,
151.06, 139.75, 122.74, 114.08, 55.30, 48.29, 46.81, 37.45, 25.07, 21.89. For C18H20N2O2S (328.4)
calculated: 65.83% C, 6.14% H, 8.53% N; found: 65.78% C, 6.11% H, 7.48% N.
General Procedure for Preparation of 1-(4-Substituted Phenyl)-
4-oxo-2-thioxo-1,3-diazaspiro[5.5]undecanes IVa, IVc – IVf
To a solution of the thiourea II (10 mmol) in ethanol (80 ml) was added dropwise 2 M NaOH
(10 ml). After 15 min water was added and the mixture was neutralized with 2 M HCl. The precipi-
tate was filtered off, dried and crystallized.
1-Phenyl-4-oxo-2-thioxo-1,3-diazaspiro[5.5]undecane(IVa), yield 87%, m.p. 178 – 180 °C (ethanol).
1
IR spectrum (CHCl3): 1 604 (C=N); 1 708 (C=O); 3 380 (NH). H NMR spectrum (CDCl3): 1.60 m,
10 H (C6H10); 2.98 s, 2 H (CH2−CO); 7.27 m, 5 H (C6H5); 9.25 bs, 1 H (NH). 13C NMR spectrum
(DMSO): 179.22, 165.90, 140.51, 129.61, 128.61, 127.67, 61.68, 34.13, 24.31, 21.59. For
C15H18N2OS (274.4) calculated: 65.66% C, 6.61% H, 10.21% N; found: 65.59% C, 6.56% H,
10.16% N.
1-(4-Bromophenyl)-4-oxo-2-thioxo-1,3-diazaspiro[5.5]undecane (IVc), yield 78%, m.p. 210 °C
(ethanol). IR spectrum (CHCl3): 1 705 (C=O); 3 380 (NH). 1H NMR spectrum (CDCl3): 1.90 m,
10 H (C6H10); 3.26 s, 2 H (CH2); 7.65 m, 4 H (C6H4); 11.45 bs, 1 H (NH). 13C NMR spectrum
(DMSO): 179.33, 165.90, 139.88, 131.97, 131.63, 123.04, 115.58, 61.83, 34.13, 24.35, 21.55. For
C15H17BrN2OS (353.3) calculated: 51.00% C, 4.85% H, 7.93% N; found: 50.97% C, 4.81% H,
7.89% N.
1-(4-Methylphenyl)-4-oxo-2-thioxo-1,3-diazaspiro[5.5]undecane(IVd), yield 80%, m.p. 204 – 206 °C
1
(ethanol). IR spectrum (KBr): 1 718 (C=O); 3 380 (NH). H NMR spectrum (CDCl3): 1.61 m, 10 H
Collect. Czech. Chem. Commun. (Vol. 59) (1994)