P. P. Mohire, D. R. Chandam, R. B. Patil, D. R. Kumbhar, S. J. Jadhav,
A. A. Patravale, V. P. Godase, J. S. Ghosh, and M. B. Deshmukh
Vol 000
65.93; H, 3.60; N, 7.69% Found: C, 65.86; H, 3.52; N,
7.54%.
2-Amino-4-(5-bromo-2-hydroxyphenyl)-7-methyl-5-oxo-
4H,5H-pyrano[4,3-b]pyran-3-carbonitrile (Table 3 Entry 4,
compd. code PD). White solid; yield 87%; mp 282°C;
2-Amino-4-(4-chlorophenyl)-7-methyl-5-oxo-4H,5H-
pyrano[4,3-b]pyran-3-carbonitrile (Table 3 Entry 8, compd.
code PH).
White solid; yield 92%; mp 232°C; IR (ν
max): 3380.60, 3322.75, 3194.51, 2200.38, 1712.48,
1644.02, 1611.23 cmÀ1 1H NMR (300 MHz,
;
IR (ν max): 3346.85, 3061.44, 2363.34, 1785.76,
DMSO-d6): δ, 1.586 (s, 3H, ─CH3), 2.268 (s, 2H,
─NH2), 4.479 (s, 1H, ─CH), 5.928–5.930 (d, 1H,
J = 0.6 Hz, Ar─H), 7.231–7.329 (m, 5H, Ar─H) ppm;
mass (m/z): 314.72314 (M+). Anal. Calcd for
C16H11ClN2O3: C, 61.06; H, 3.52; N, 8.90% Found: C,
60.98; H, 3.30; N, 8.84%.
2-Amino-7-methyl-5-oxo-4-phenyl-4H,5H-pyrano[4,3-b]
pyran-3-carbonitrile (Table 3 Entry 9, compd. code PI).
White solid; yield 88%; mp 236°C; IR (ν max): 3392.17,
1731.76, 1691.27 cmÀ1
;
1H NMR (300 MHz,
DMSO-d6): δ, 2.162 (s, 3H, CH3), 4.270 (s, 1H, ─CH),
6.013 (s, 1H, ─OH), 6.500 (s, 2H, NH2), 7.109–7.240
(m, 4H, Ar─H), 7.670 (s, 1H, Ar─H) ppm; 13C NMR
(75 MHz, DMSO-d6): δ, 19.17, 36.57, 58.50, 98.58,
101.13, 119.80, 127.52, 127.76, 128.82, 143.65, 158.64,
158.88, 162.19, 163.23 ppm; mass (m/z): 375.17354
(M+). Anal. Calcd for C16H11BrN2O4: C, 51.22; H, 2.96;
N, 7.47% Found: C, 51.04; H, 2.84; N, 7.38%.
3320.82, 3181.00, 2197.49, 1704.76, 1671.98, 1642.09,
1612.20 cmÀ1 1H NMR (300 MHz, DMSO-d6): δ,
;
2-Amino-4-(3-methoxyphenyl)-7-methyl-5-oxo-4H,5H-
pyrano[4,3-b]pyran-3-carbonitrile (Table 3 Entry 5, compd.
2.212(s, 3H, 0CH3), 4.266 (s, 1H, ─CH), 6.234 (s, 1H,
Ar─H), 7.138–7.198 (t, 1H, J = 9.0 Hz, Ar─H), 7.231 (s,
3H, Ar─H), 7.274–7.321 (t, 2H, J = 7.2 Hz, ─NH2) ppm;
mass (m/z): 280.27808 (M+). Anal. Calcd for
C16H12N2O3: C, 68.56; H, 4.32; N, 9.99% Found: C,
68.42; H, 4.10; N, 9.78%.
code PE).
White solid; yield 94%; mp 238°C; IR (ν
max): 3322.75, 3182.93, 3097.12, 2205.20, 1702.84,
1
1671.98, 1643.05, 1608.34 cmÀ1; H NMR (300 MHz,
DMSO-d6): δ, 2.214 (s, 3H, ─CH3), 3.728 (s, 3H,
─OCH3), 4.237 (s, 1H, ─CH), 6.208 (s, 1H, Ar─H),
6.713–6.789 (t, 3H, J = 9.3 Hz, Ar─H), 7.101 (s, 2H,
Ar─H), 7.180–7.232 (t, 1H, J = 7.8 Hz, Ar─H) ppm; 13C
NMR (75 MHz, DMSO-d6): δ, 19.80, 36.58, 55.32,
58.35, 98.51, 101.10, 112.19, 114.09, 119.69, 119.92,
129.92, 145.34, 158.63, 158.74, 159.60, 162.02,
163.11 ppm; mass (m/z): 310.30406 (M+). Anal. Calcd
for C17H14N2O4: C, 65.80; H, 4.55; N, 9.03% Found: C,
65.68; H, 4.46; N, 8.98%.
2-Amino-4-(4-methoxyphenyl)-7-methyl-5-oxo-4H,5H-
pyrano[4,3-b]pyran-3-carbonitrile (Table 3 Entry 10, compd.
code PJ).
Yellow solid; yield 80%; mp 214°C; IR (ν
max): 3348.78, 3188.72, 3087.48, 2191.7, 1698.02,
1
1671.98, 1640.16, 1605.45 cmÀ1; H NMR (300 MHz,
DMSO-d6): δ, 2.250 (s, 3H, ─CH3), 3.794 (s, 3H,
─OCH3), 4.445 (s, 1H, ─CH), 5.910 (s, 2H, ─NH2),
6.839–6.878 (m, 2H, Ar─H), 7.017–7.280 (m, 3H,
Ar─H) ppm; mass (m/z): 310.30406 (M+). Anal. Calcd
for C17H14N2O4: C, 65.80; H, 4.55; N, 9.03% Found: C,
65.77; H, 4.48; N, 8.94%.
2-Amino-4-(2-chlorophenyl)-7-methyl-5-oxo-4H,5H-
pyrano[4,3-b]pyran-3-carbonitrile (Table 3 Entry 6, compd.
code PF).
White solid; yield 90%; mp 268°C; IR (ν
max): 3338.18, 3103.87, 2190.74, 1748.16, 1698.02,
2-Amino-4-(4-cyanophenyl)-7-methyl-5-oxo-4H,5H-
pyrano[4,3-b]pyran-3-carbonitrile (Table 3 Entry 11, compd.
1
1671.02, 1632.45, 1605.45 cmÀ1; H NMR (300 MHz,
code PK).
White solid; yield 86%; mp 228°C; IR (ν
DMSO-d6): δ, 2.228 (s, 3H, ─CH3), 4.792 (s, 1H, ─CH),
6.230 (s, 1H, Ar─H), 7.147 (s, 2H, Ar─H), 7.181–7.271
(m, 3H, ─NH2, Ar─H), 7.342–7.366 (d, 1H, J = 7.2 Hz,
Ar─H) ppm; 13C NMR (75 MHz, DMSO-d6): δ, 19.82,
34.20, 57.00, 98.39, 100.02, 119.32, 127.88, 129.09,
129.98, 130.80, 132.88, 140.52, 158.77, 159.33, 161.77,
163.46 ppm; mass (m/z): 314.72314 (M+). Anal. Calcd
for C16H11ClN2O3: C, 61.06; H, 3.52; N, 8.90% Found:
C, 60.90; H, 3.48; N, 8.82%.
max): 3350.71 3192.58, 2929.34, 2228.3, 2274.63,
2200.38, 1724.05, 1678.73, 1647.88, 1610.27 cmÀ1; H
1
NMR (300 MHz, DMSO-d6): δ, 1.600 (s, 3H, ─CH3),
2.281 (s, 2H, ─NH2), 4.784 (s, 1H, ─CH), 7.418–7.445
(d, 1H, J = 8.1 Hz, Ar─H), 7.633–7.660 (d, 1H,
J = 8.1 Hz, Ar─H), 7.838–7.868 (d, 2H, J = 9.0 Hz,
Ar─H), 8.002–8.030 (d, 1H, J = 8.4 Hz, Ar─H) ppm;
mass (m/z): 305.28754 (M+). Anal. Calcd for
C17H11N3O3: C, 66.88; H, 4.28; N, 8.94% Found: C,
66.76; H, 4.14; N, 8.82%.
2-Amino-4-(3-chlorophenyl)-7-methyl-5-oxo-4H,5H-
pyrano[4,3-b]pyran-3-carbonitrile (Table 3 Entry 7, compd.
code PG).
White solid; yield 93%; mp 256°C; IR (ν
max): 3392.17, 3322.75, 3195.47, 3096.15, 2196.52,
1704.76, 1671.98, 1644.02, 1613.16 cmÀ1 1H NMR
2-Amino-4-(3-bromophenyl)-7-methyl-5-oxo-4H,5H-
pyrano[4,3-b]pyran-3-carbonitrile (Table 3 Entry 12, compd.
code PL).
White solid; yield 83%; mp 216°C; IR (ν
max): 3320.82, 3193.54, 3103.87, 2197.49, 1703.8,
1671.98, 1643.05, 1613.16 cmÀ1 1H NMR (300 MHz,
;
(300 MHz, DMSO-d6): δ, 2.219 (s, 3H), 4.311 (s, 1H),
6.226 (s, 1H), 7.139–7.198 (t, 3H, J = 7.5 Hz, ─NH2,
Ar─H), 7.231–7.258 (d, 1H, J = 8.1 Hz, Ar─H), 7.297–
7.348 (t, 1H, J = 7.2 Hz, Ar─H) ppm; mass (m/z):
314.72314 (M+). Anal. Calcd for C16H11ClN2O3: C, 61.06;
H, 3.52; N, 8.90% Found: C, 61.94; H, 3.56; N, 8.86%.
;
DMSO-d6): δ, 2.218 (s, 3H, ─CH3), 2.530 (s, 2H, ─NH2),
4.303 (s, 1H, ─CH), 6.235 (s, 1H, Ar─H), 7.207 (s, 1H,
Ar─H), 7.265–7.340 (t, 1H, J = 7.5 Hz, Ar─H), 7.381–
7.406 (d, 1H, J = 7.5 Hz, Ar─H) ppm; mass (m/z):
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet