SYNTHESIS AND ANTIMICROBIAL ACTIVITY
1571
–
1
spectrum, ν, cm : 3415 (OH), 3300 (NH), 1659, 1622
(
(10). A mixture of compound 6 (3.75 g, 10 mmol) with
dimethylamine (15 mL) was refluxed for 12 h then poured
into ice-cold water. The formed solid was filtered off to
give compound 10 as pale brown powder (EtOH), yield
1
2C=O, amide). H NMR spectrum, δ, ppm: 4.81 s (2H,
NH , D O exchange), 6.44 s (1H, Haryl), 6.47d (2H, J =
.4 Hz, Haryl), 6.95 d (2H, J = 8.4 Hz, Haryl), 7.15 d (1H,
J = 8.2 Hz, Haryl), 7.26 d (1H, J = 8.2 Hz, Haryl), 7.62 s (1H,
OH, D O exchange), 9.62 s (1H, NH, D O exchange). C
2
2
8
–1
65%, mp 280°C (decomp.). IR spectrum, ν, cm : 3430
13
1
(OH and NH), 1642 (C=O, amide). H NMR spectrum, δ,
2
2
NMR spectrum, δ, ppm: 102.6, 112.7, 116.5, 128.5, 129.2,
30.3, 130.7, 148.0, 149.4, 157.2, 161.3, 168.7. Found
ppm: 2.23 s (6H, 2CH , H
), 3.35 s (2H, NCH ), 5.04 s
3
methyl 2
1
(1H, Hpyran), 6.54 d (1H, J = 8.4 Hz, Haryl), 6.56 s (1H,
Haryl), 6.99 d (1H, J = 8.4 Hz, Haryl), 7.20 d (2H, J =
8.4 Hz, Haryl), 7.27 d (2H, J = 8.4 Hz, Haryl), 7.94 s (1H,
%
: C 1.03; H 3.49; N 8.87. C H ClN O . Calculated,
16 11 2 3
%
: C 61.06; H 3.52; N 8.90.
Ethyl 2-(5-(4-chlorophenyl)-8-hydroxy-4-oxo-4,5-
dihydro-3H-chromeno[2,3-d]pyrimidin-2-yl)acetate
8). A mixture of compound 1 (2.98 g, 10 mmol) with
OH, D O exchange), 10.21 s (1H, NH, D O exchange).
2
2
Found %: C 62.58; H 4.71; N 10.97. C H ClN O .
Calculated, %: C 62.58; H 4.73; N 10.95.
20 18
3
3
(
diethyl malonate (1.6 g, 10 mmol) was fused for 30 min.
The formed mixture was crystallized from ethanol to give
compound 8 as brown powder of pure compound 8, yield
5-(4-Chlorophenyl)-8-hydroxy-2-(morpholino-
methyl)-3H-chromeno[2,3-d]pyrimidin-4(5H)-one
(11). A mixture of compound 6 (3.75 g, 10 mmol) with
morpholine (0.87 mL, 10 mmol) in DMF (15 mL) was
refluxed for 24 h then poured into ice-cold water and
neutralized by conc. HCl. The resulting precipitate was
filtered off to give compound 11 as pale brown powder,
–1
3
6%, mp 158–160°C. IR spectrum, ν, cm : 3421 (OH and
1
NH), 1731 (C=O, ester), 1616 (C=O, amide). H NMR
spectrum, δ, ppm: 1.17 t (3H, J = 7.0 Hz, CH CH ), 2.89 s
3
2,
(
2H, CH CO), 4.09 q (2H, J = 7.0 Hz, CH CH ), 4.41 s
2 3 2
–1
(1H, Hpyran), 6.65 s (1H, Haryl), 6.86 d (1H, J = 8.8 Hz,
yield 42%, mp 228–230°C. IR spectrum, ν, cm : 3440
1
Haryl), 7.11 d (1H, J = 8.8 Hz, Haryl), 7.57 d (2H, J =
.4 Hz, Haryl), 7.72 d (2H, J = 8.4 Hz, Haryl), 9.80 s (1H,
(OH), 1641 (C=O, amide). H NMR spectrum, δ, ppm:
8
3.36 m (4H, 2OCH ), 3.57 (m, 6H, 3NCH ), 5.04 s (1H,
2
2
1
3
OH, D O exchange), 13.21 s (NH, D O exchange). C
Hpyran), 6.51 s (1H, Haryl), 6.54 d (1H, J = 8.4 Hz, Haryl),
6.96 d (1H, J = 8.4 Hz, Haryl), 7.18 d (2H, J = 8.4 Hz,
2
2
NMR spectrum, δ, ppm: 14.34, 36.28, 61.34, 63.51, 96.71,
1
1
1
03.3, 110.8, 111.7, 112.2, 115.2, 129.2, 129.5, 130.8,
36.1, 141.2, 156.4, 158.1, 158.2, 162.8, 162.9, 165.2,
67.0. Found %: C 61.14; H 4.12; N 6.75. C H ClN O .
Haryl), 7.27 d (2H, J = 8.4 Hz, Haryl), 8.01 s (1H, OH, D O
2
exchange), 9.74 s (1H, NH, D O exchange). Found %: C
2
62.03; H 4.69; N 9.88. C H ClN O . Calculated, %: C,
21
17
2
5
22 20
3
4
Calculated, %: C, 61.10; H, 4.15; N, 6.79.
62.05; H, 4.73; N, 9.87.
2
-[5-(4-Chlorophenyl)-8-hydroxy-4-oxo-4,5-di-
5-(4-Chlorophenyl)-8-hydroxy-2-(piperidin-1-yl-
methyl)-3H-chromeno[2,3-d]pyrimidin-4(5H)-one
(12). A mixture of compound 6 (3.75 g, 10 mmol) with
piperidine (0.97 mL, 10 mmol) in DMF (15 mL) was
refluxed for 24 h then poured into ice-cold water and
neutralized with conc. HCl to give compound 12 as dark
brown powder (EtOH), yield 83%, mp 240–242°C. IR
hydro-3H-chromeno[2,3-d]pyrimidin-2-yl]acetic
acid (9). A mixture of compound 8 (4.12 g, 10 mmol)
with potassium hydroxide (1.12 g, 10 mmol) in absolute
ethanol (15 mL) was refluxed for 6 h. The reaction mixture
was poured into ice-water, neutralized with dil. HCl
solution and filtered off to give compound 9 as dark brown
powder (EtOH), yield 52%, mp 260–262°C. IR spectrum,
–
1
1
spectrum, ν, cm : 3440 (OH), 1641 (C=O, amide). H
–
1
ν, cm : 3411 (OH and NH), 1690 (C=O, acid), 1616
C=O, amide). H NMR spectrum, δ, ppm: 3.16 s (2H,
NMR spectrum, δ, ppm: 1.36 m (2H, CH ), 1.48 m (4H,
2
1
(
2CH ), 2.45 m 4H (2NCH , piperidine), 2.55 (2H, NCH ),
2
2
2
OCH ), 5.04 s (1H, Hpyran), 6.17 s (1H, Haryl), 6.54 d (1H,
J = 8.4 Hz, Haryl), 7.28 d (1H, J = 8.4 Hz, Haryl), 7.52 d
5.04 s (1H, Hpyran), 6.52 d (1H, J = 8.4 Hz, Haryl), 6.57
s (1H, Haryl), 6.96 d (1H, J = 8.4 Hz, Haryl), 7.18 d (2H,
J = 8.8 Hz, Haryl),7.27 d (2H, J = 8.4 Hz, Haryl), 7.94 s (1H,
OH, D O exchange), 9.99 s (1H, NH, D O exchange).
2
(2H, J = 8.4 Hz, Haryl), 7.60 d (2H, J = 8.4 Hz, Haryl),
8
.62 s (1H, OH D O exchange), 10.02 s (1H, OHacid,
,
2
2
2
D O exchange), 12.42 s (NH, D O exchange). Found %:
Found %: C 65.19; H 5.26; N 9.87. C H ClN O .
2
2
23 22 3 3
C 59.29; H 3.38; N 7.30. C H ClN O . Calculated, %:
Calculated, %: C 65.17; H 5.23; N 9.91.
1-(4-Chlorophenyl)-8-hydroxy-3,4-dihydro-
chromeno[2′,3′:4,5]pyrimido[1,2-d][1,2,3,4]tetrazin-
12(11H)-one (13). A mixture of compound 6 (3.7 g,
1
9
13
2
5
C 59.31; H 3.41; N 7.28.
-(4-Chlorophenyl)-2-[(dimethylamino)methyl]-
-hydroxy-3H-chromeno[2,3-d]pyrimidin-4(5H)-one
1
5
8
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 90 No. 8 2020