748
G. Biagi, I. Giorgi, O. Livi, F. Pacchini, O. L. Salerni, and V. Scartoni
Vol. 42
Table 3
13C nmr data ( , ppm, DMSO-d6) of the compounds 8-15 and 19-26.
Compound
Purine and phenyl carbons
Others
8
155.3; 149.9; 146.3; 145.3; 136.8; 135.6; 128.7; 128.5; 128.3;
127.6; 127.3; 127.0; 123.9
45.8 (CH2-N); 35.9 (CH2-S)
9
159.2; 156.1; 150.4; 145.6; 137.0; 135.8; 128.9; 127.7; 127.4;
127.3; 118.3
45.7 (CH2-N); 35.9 (CH2-S); 27.4 (CH2); 11.6 (CH3)
10
11
12
13
14
15
19
20
21
156.3; 154.0; 150.2; 147.6; 137.6; 136.4; 129.6; 129.3; 129.1;
128.5; 128.1; 127.9; 124.2
156.9; 153.4; 151.1; 147.6; 137.7; 136.6; 132.8; 132.0; 129.6;
129.4; 129.2; 128.5; 128.4; 128.2; 128.1; 123.4
166.0; 156.3; 148.9; 143.0; 135.7; 131.3; 129.0; 128.8; 128.5;
127.9; 127.8; 127.0; 123.7
162.7; 156.9; 149.9; 142.6; 135.8; 131.3; 128.9; 128.7; 128.5,
127.8; 127.3; 126.6; 120.9
156.6; 156.5; 149.0; 143.3; 135.7; 131.3; 128.9; 128.5; 128.4;
127.8: 127.2; 126.5; 123.1
99.3 (O-CH-O); 63.1 (CH2-O); 46.6 (CH2-N); 36.7 (CH2-
S); 15.7 (CH3)
46.6 (CH2-N); 36.7 (CH2-S)
60.5 (CH2-SO2); 47.1 (CH2-N)
60.5 (CH2-SO2); 46.9 (CH2-N); 27.6 (CH2); 11.2 (CH3)
98.5 (O-CH-O); 62.5 (CH2-O); 60.5 (CH2-SO2); 47.1
(CH2-N); 15.0 (CH3)
60.5 (CH2-SO2); 46.9 (CH2-N)
156.5; 156.6; 149.8; 143.0, 136.9, 135.7; 131.6; 131.2; 128.8;
128.5; 128.4; 127.9; 127.6; 127.4; 127.2; 126.5; 118.1
164.0; 158.0; 146.1; 136.2; 132.0; 128.9; 128.5; 128.4; 127.5;
127.4; 127.1; 113.9; 113.5
55.0 (CH3-O); 45.2 (CH2-N); 35.9 (CH2-S); 32.0 (CH2);
12.9 (CH3)
133.4 (CH=);118.0 (CH2=); 45.3 (CH2-N);
34.7 (CH2-S)
133.5 (CH=);118.6 (CH2=); 46.1 (CH2-N);
35.6 (CH2-S); 27.7 (CH2); 11.8 (CH3)
45.4 (CH2-N)
168.4; 150.9; 150.2; 143.0; 136.6; 128.3; 127.4; 127.0; 118.1
159.5; 156.3; 150.1; 145.6; 136.5; 128.9; 128.0; 127.6; 122.3
22
23
24
25
166.4; 150.5; 147.1; 146.4; 136.1; 128.3; 127.6; 127.4; 112.3
166.1; 160.2; 151.1; 147.5; 136.2; 128.3; 127.9; 127.4; 110.1
166.7; 154.2; 150.8; 146.6; 136.1; 128.3; 127.8; 127.4; 111.8
155.2; 149.3; 147.8; 147.2; 135.8; 128.6; 127.7; 127.1; 119.3
45.3 (CH2-N); 27.3 (CH2); 11.4 (CH3)
98.3 (O-CH-O); 62.4 (CH2-O); 45.5 (CH2-N); 15.0 (CH3)
45.9 (CH2-N); 30.8, 29.1, 27.7, 25.6, 21.9 (5 CH2); 13.9
(CH3)
26
159.2; 156.3; 150.0; 146.1; 136.0; 128.6; 127.7; 127.2; 121.9
45.7 (CH2-N); 31.9, 30.7, 28.9, 27.7, 27.5, 22.0 (6 CH2);
13.9, 11.7 (2 CH3)
ethanol (0.5 mL), some drops of N,N-diethylaniline were added.
The mixture was stirred at 110 °C in a stopped vial for 2 hours;
after cooling, the precipitate was collected by filtration and crys-
tallized. See Table 1 for yields, crystallization solvent, physico-
chemical properties and elemental analysis; see Table 2 and 3 for
ir and nmr data.
was stirred to a room temperature for 1 hour. Then the mixture
reaction was diluted with water and extracted with chloroform.
The organic phase was evaporated and the residue was triturated
with ethyl ether. The solid was collected by filtration and crystal-
lized. See Table 1 for yields, crystallization solvent, physico-
chemical properties and elemental analysis; see Table 2 and 3 for
ir and nmr data.
8-Mercapto-9-phenylmethyl-1,9-dihydropurin-6-one (22) and 8-
Mercapto-9-phenylmethyl-2-substituted-1,9-dihydropurin-6-one
(23-24).
8-Benzyl-9-phenylmethyl-1,9-dihydro-purin-6-one (8), 2-Ethyl-
8-benzyl-9-phenylmethyl-1,9-dihydropurin-6-one (9) from 22
and 23 Respectively.
5-Amino-2-mercapto-1-phenylmethyl-1H-imidazole-4-car-
boxylic acid amide (5) (0.365 g, 1.47 mmoles) was added to a
solution of sodium ethoxide prepared from sodium (0.23 g, 0.01
mole) in 8.5 mL of absolute ethanol. The mixture was then
refluxed with stirring for 1 hour. A solution of the appropriate
ester (7.5 mmoles) in 5 mL of ethanol was added dropwise and
the solution was stirred under reflux for 48 hours. After cooling,
ice was added and then the mixture was neutralized with 50%
acetic acid. The precipitate formed was collected by filtration and
crystallized. See Table 1 for yields, crystallization solvent,
physicochemical properties and elemental analysis; see Table 2
and 3 for ir and nmr data.
A solution consisting of 22 or 23 (1.19 mmoles), the minimal
amount of N,N-dimethylformamide, benzyl bromide (1.18
mmoles) and 1,8-diazabicyclo[5.4.0]undec-7-ene (1.18 mmoles)
was stirred to a room temperature for 1 hour. Then the mixture
reaction was diluted with water and extracted with chloroform.
The organic phase was evaporated and the residue was triturated
with ethyl ether. The solid was collected by filtration and crys-
tallized. See Table 1 for yields, crystallization solvent, physico-
chemical properties and elemental analysis; see Table 2 and 3 for
ir and nmr data.
Treatment of Compounds 12-15 with Amines.
8-Hexylsulfanyl-9-phenylmethyl-1,9-dihydro-purin-6-one (25)
and 2-Ethyl-8-hexylsulfanyl-9-phenylmethyl-1,9-dihydro-purin-
6-one (26).
Compounds 12-15 (1 mmol) were treated in turn with an
excess of n-butylamine or benzylamine (3 ml); the mixture was
heated at 120° for 2 h. The following dilution with cold 10%
hydrochloric acid allowed the nearly complete recovering of the
starting products.
A solution consisting of 22 or 23 (1.19 mmoles), the minimal
amount of N,N-dimethylformamide, 1-bromohexane (1.18
mmoles) and 1,8-diazabicyclo[5.4.0]undec-7-ene (1.18 mmoles)