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added to a solution of 0.01 mol of methyl benzoyl-
pyruvate in 10 mL of glacial acetic acid. The reaction
mixture was refluxed for 3–5 min. After cooling, the
precipitate formed was treated with ethanol, filtered off
and recrystallized from glacial acetic acid. Yield 3.43 g
(72%), mp 298–300°С. IR spectrum, ν, cm–1: 3376,
3344, 3280 [NHC(=NH)NH2], 3152 (ОН), 1692
[NHC(=NH)NH2], 3180 (ОН), 1680 (СОN), 1624
(С=О), 1365, 1135 (SО2). Н NMR spectrum, δ, ppm:
1
1.10, 1.05 d [6Н, (СН3)2СН, J 5.57 Hz], 2.33 s (3Н, 4-
СН3С6Н4СО), 2.58–2.90 m [1Н, (СН3)2СН], 6.21 s
(1Н, С5Н), 6.56 s [4Н, NHC(=NH)NH2], 6.93–7.63 m
(12Н, СНAr), 11.00 br.s (1Н, ОН). Found, %: С 63.02,
63.27; Н 5.23, 5.38; N 10.43, 10.64; S 5.94, 6.11.
С28H28N4O5S. Calculated, %: С 63.14; Н 5.30; N
10.52; S 6.02.
1
(СОN), 1628 (С=О), 1388, 1144 (SО2). Н NMR
spectrum, δ, ppm: 6.34 s (1Н, С5Н), 6.64 s [4Н, NHC
(=NH)NH2], 7.06–7.64 m (14Н, СНAr), 11.72 br.s (1Н,
ОН). Found, %: С 60.60, 60.38; Н 4.15, 4.31; N 11.66,
11.86; S 6.64, 6.82. С24H20N4O5S. Calculated, %: С
60.49; Н 4.23; N 11.76; S 6.73.
3-Hydroxy-1-(4-guanidylsulfonyl)-5-(2-fluoro-
phenyl)-4-(4-chlorobenzoyl)-3-pyrrolin-2-one (VI) was
obtained similarly. Yield 4.23 g (80%), mp 273–275°С.
IR spectrum, ν, cm–1: 3424, 3336 [NHC(=NH)NH2],
3192 (ОН), 1692 (СОN), 1636 (С=О), 1384, 1144
4-Benzoyl-5-(4-bromophenyl)-3-hydroxy-1-(4-
guanidylsulfonylphenyl)-3-pyrrolin-2-one (II) was
prepared similarly. Yield 3.66 g (66%), mp 244–246°С.
IR spectrum, ν, cm–1: 3416, 3288 [NHC(=NH)NH2],
3192 (ОН), 1692 (СОN), 1628 (С=О), 1384, 1144
1
(SО2). Н NMR spectrum, δ, ppm: 6.43 s (1Н, С5Н),
6.58 s [4Н, NHC(=NH)NH2], 6.78–7.86 m (12Н,
СНAr), 11.80 br.s (1Н, ОН). Found, %: С 54.37, 54.62;
Н 3.37, 3.50; N 10.50, 10.70; S 5.98, 6.15.
С24H18ClFN4O5S. Calculated, %: С 54.50; Н 3.43; N
10.59; S 6.06.
1
(SО2). Н NMR spectrum, δ, ppm: 6.26 s (1Н, С5Н),
6.56 s [4Н, NHC(=NH)NH2], 7.28–7.60 m (13Н,
СНAr). Found, %: С 52.01, 51.79; Н 3.38, 3.52; N
10.00, 10.18; S 5.69, 5.85. С24H19BrN4O5S. Calculated,
%: С 51.90; Н 3.45; N 10.09; S 5.77.
3-Hydroxy-1-(4-guanidylsulfonylphenyl)-5-(4-
nitrophenyl)-4-(4-chlorobenzoyl)-3-pyrrolin-2-one
(VII) was obtained similarly. Yield 4.34 g (78%), mp
244–246°С. IR spectrum, ν, cm–1: 3416, 3376 [NHC·
(=NH)NH2], 3208 (ОН), 1696 (СОN), 1632 (С=О),
4-Benzoyl-3-hydroxy-1-(4-guanidylsulfonylphenyl)-
5-(4-chlorophenyl)-3-pyrrolin-2-one (III) was prepared
similarly. Yield 3.83 g (75%), mp 255–257°С. IR
spectrum, ν, cm–1: 3416, 3344 [NHC(=NH)NH2], 3200
(ОН), 1696 (СОN), 1632 (С=О), 1380, 1144 (SО2). 1Н
NMR spectrum, δ, ppm: 6.29 s (1Н, С5Н), 6.57 s [4Н,
NHC(=NH)NH2], 7.09–7.72 m (13Н, СНAr). Found,
%: С 56.29, 56.56; Н 3.69, 3.83; N 10.87, 11.06; S
6.20, 6.37. С24H19ClN4O5S. Calculated, %: С 56.42; Н
3.75; N 10.97; S 6.28.
1
1376, 1144 (SО2). Н NMR spectrum, δ, ppm: 6.46 s
(1Н, С5Н), 6.59 s [4Н, NHC(=NH)NH2], 7.34–8.00 m
(12Н, СНAr), 12.1 br.s (1Н, ОН). 13С NMR spectrum,
δC, ppm: 60.18 (С5Н), 119.13, 121.88, 123.64, 126.46,
128.44, 129.32, 130.71, 136.58, 137.73, 138.34,
141.25, 144.24, 147.37, 151.28 (=C–OH), 158.15
[NHC(=NH)NH2], 164.87 (N–C=O), 187.89 (С=О).
Found, %: С 51.74, 51.95; Н 3.19, 3.31; N 12.51, 12.7;
S 5.69, 5.85. С24H18ClN5O7S. Calculated, %: С 51.85;
Н 3.26; N 12.60; S 5.77.
3-Hydroxy-5-(4-hydroxyphenyl)-1-(4-guanidyl-
sulfonylphenyl)-4-(4-methylbenzoyl)-3-pyrrolin-2-
one (IV) was prepared similarly. Yield 3.45 g (68%),
mp 262–264°С. IR spectrum, ν, cm–1: 3448, 3344
[NHC(=NH)NH2], 3176 (ОН), 1692 (СОN), 1628
3-Hydroxy-1-(4-guanidylsulfonylphenyl)-5-(3-
fluorophenyl)-4-(4-chlorobenzoyl)-3-pyrrolin-2-one
(VIII) was prepared similarly. a. Yield 4.07 g (77%),
mp 279–281°С. IR spectrum, ν, cm–1: 3432, 3344
[NHC(=NH)NH2], 3136 (ОН), 1692 (СОN), 1632
1
(С=О), 1388, 1144 (SО2). Н NMR spectrum, δ, ppm:
2.35 s (3Н, СН3), 6.12 s (1Н, С5Н), 6.56 s [4Н, NHC·
(=NH)NH2], 7.02–7.59 m (12Н, СНAr), 9.12 s (1Н,
ОН, phenol), 11.1 br.s (1Н, ОН, enol). Found, %: С
59.12, 59.40; Н 4.30, 4.45; N 10.95, 11.16; S 6.24,
6.41. С25H22N4O6S. Calculated, %: С 59.28; Н 4.38; N
11.06; S 6.33.
1
(С=О), 1392, 1144 (SО2). Н NMR spectrum, δ, ppm:
6.28 s (1Н, С5Н), 6.55 s [4Н, NHC(=NH)NH2], 6.81–
7.68 m (12Н, СНAr). Found, %: С 54.39, 54.61; Н
3.35, 3.50; N 10.49, 10.68; S 5.99, 6.13. С24H18Cl·
FN4O5S. Calculated, %: С 54.50; Н 3.43; N 10.59; S
6.06.
3-Hydroxy-1-(4-guanidylsulfonylphenyl)-5-(4-
isopropylphenyl)-4-(4-methylbenzoyl)-3-pyrrolin-2-
one (V) was prepared similarly. Yield 3.78 g (71%),
mp 255–257°С. IR spectrum, ν, cm–1: 3420, 3340
b. A solution of equimolar amount of methyl 4-
chlorobenzoylpyruvate in 10 mL of glacial acetic acid
was added to a solution of 0.01 mol of Schiff base IX
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 2 2014