Medicinal Chemistry Research
Spectral data of synthesized pyrano[3,2-b]pyran
derivatives
1349, 1217 cm–1. 1H NMR (400 MHz, DMSO-d6) δ =
8.31–8.27 (2H, m, Ar-H), 7.91 (1H, d, J = 8 Hz, Ar-H),
7.79–7.83 (1H, t, J = 8 Hz, Ar-H), 7.49 (2H, s, NH2), 6.44
(1H, s, H-7), 5.78 (1H, t, J = 6.0 Hz, OH), 5.23 (1H, s, H-
4), 4.30 (1H, dd, J = 6.0. 16.0 Hz, CH2),4.22 (1H, dd, J =
6.0. 16.0 Hz, CH2) ppm. 13C NMR (100 MHz, DMSO-d6)
δ = 170.5, 168.9, 160.1, 148.6, 147.9, 143.2, 137.0, 135.3,
131.4, 123.6, 122.8, 119.5, 112.3, 59.5, 55.4 ppm.
2-amino-4-(phenyl)-4,8-dihydro-6-(hydroxymethyl)-8-
oxo-pyrano[3,2-b]pyran-3-carbonitrile (4a): White solid;
m.p. 222–224 °C; IR (KBr, ν): 3373, 3313, 3197, 3067,
2864, 2197, 1646, 1592, 1445, 1217 cm–1. 1H NMR
(400 MHz, DMSO-d6) δ = 7.53–7.25 (5H, m, Ar-H), 7.40
(2H, s, NH2), 6.42 (1H, s, H-7), 5.76 (1H, t, J = 6.0 Hz,
OH), 4.91 (1H, s, H-4), 4.26 (1H, dd, J = 6.0, 16.0 Hz,
CH2), 4.17 (1H, dd, J = 6.0, 16.0 Hz, CH2) ppm. 13C NMR
(100 MHz, DMSO-d6) δ = 169.1, 168.2, 158.7, 148.2,
140.1, 136.4, 129.7, 128.5, 127.5, 118.4, 111.3, 59.1, 55.2,
45.3 ppm.
2-amino-4-(4-nitrophenyl)-4,8-dihydro-6-(hydro-
xymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile (4f):
Yellow solid; m.p. 230–232 °C; IR (KBr, ν): 3535, 3451,
3327, 3173, 3082, 2944, 2907, 2871, 2194, 1649, 1590,
1
1520, 1446, 1349, 1261, 1204 ppm. H NMR (400 MHz,
DMSO-d6) δ = 8.35 (2H, d, J = 8.8 Hz, Ar-H), 7.72 (2H, d,
J = 8.8 Hz, Ar-H), 7.48 (2H, s, NH2), 6.441 (1H, s, H-7),
5.78 (1H, t, J = 6.0 Hz, OH), 5.173 (1H, s, H-4), 4.29 (1H,
dd, J = 6.0. 16.2 Hz, CH2), 4.21 (1H, dd, J = 6.0 16.2 Hz,
CH2) ppm. 13C NMR (100 MHz, DMSO-d6) δ = 170.5,
168.8, 160.9, 149.2, 148.0, 143.8, 129.8, 124.1, 118.5,
117.0, 114.6, 112.5, 59.8, 54.4 ppm.
2-amino-4-(4-chlorophenyl)-4,8-dihydro-6-(hydro-
xymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile
(4b): White solid; m.p. 216–218 °C; IR (KBr, ν): 3376,
3305, 3188, 3080, 2863, 2193, 1638, 1597, 1487,
1
1208 cm–1. H NMR (400 MHz, DMSO-d6) δ = 7.48 (2H,
d, J = 8.0 Hz, Ar-H), 7.35 (2H, d, J = 8.0 Hz, Ar-H), 7.41
(2H, s, NH2), 6.38 (1H, s, H-7), 5.78 (1H, t, J = 6.0 Hz,
OH), 5.45 (1H, s, H-4), 4.29 (1H, dd, J = 6.0, 16.0 Hz,
CH2), 4.21(1H, dd, J = 6.0, 16.0 Hz, CH2) ppm. 13C NMR
(100 MHz, DMSO-d6) δ = 169.5, 165.4, 159.2, 148.5,
139.9, 136.1, 132.5, 129.7, 128.9, 119.1, 113.7, 59.5, 55.3,
37.2 ppm.
2-amino-4-(4-cyano-phenyl)-4,8-dihydro-6-(hydro-
xymethyl)-8-oxo-pyrano[3,2-b]pyran3-carbonitrile (4g):
Light yellow solid; m.p. 234–237 °C; IR (KBr, ν): 3578,
3429, 3332, 3218, 2900, 2192, 1626, 1592, 1420,
1
1199 cm–1. H NMR (400 MHz, DMSO-d6) δ = 7.97 (2H,
d, J = 8.4 Hz, Ar-H), 7.62 (2H, d, J = 8.4 Hz, Ar-H), 7.45
(2H, s, NH2), 6.44 (1H, s, H-7), 5.78 (1H, t, J = 6.0 Hz,
OH), 4.28 (1H, s, H-4), 4.29 (1H, dd, J = 6.0. 16.2 Hz,
CH2), 4.21 (1H, dd, J = 6.0. 16.2 Hz, CH2) ppm. 13C NMR
(100 MHz, DMSO-d6) δ = 170.1, 168.8, 160.1, 148.4,
146.9, 137.5, 133.2, 129.1, 119.2, 118.9, 112.0, 111.3,
59.5, 55.20 ppm.
2-amino-4-(4-fluoro-phenyl)-4,8-dihydro-6-(hydro-
xymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile (4c):
White solid; m.p. 240–243 °C; IR (KBr, ν): 3393, 3303,
3187, 2925, 2192, 1672, 1637, 1595, 1508, 1207 cm–1. H
1
NMR (400 MHz, DMSO-d6) δ = 7.43 – 7.46 (2H, m, Ar-
H), 7,36 (2H, s, NH2), 7.30 – 7.32 (2H, m, Ar-H), 6.43 (1H,
s, H-7), 5.79 (1H, t, J = 6.0 Hz, OH), 4.95 (1H, s, H-4),
4.31 (1H, dd, J = 6.0. 16.0 Hz, CH2), 4.22 (1H, dd, J = 6.0.
16.0 Hz, CH2) ppm. 13C NMR (100 MHz, DMSO-d6) δ =
177.8, 169.0, 164.0, 143.8, 137.9, 130.3, 128.3, 125.7,
117.8, 115.5, 111.4, 59.2, 55.4 ppm.
2-amino-4-(2,4-dichlorophenyl)-4,8-dihydro-6-
(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carboni-
trile (4h): White solid; m.p. 244–245 °C; IR (KBr, ν): 3578,
3429, 3332, 3218, 2900, 2192, 1626, 1592, 1420,
1
1199 cm–1. H NMR (400 MHz, DMSO-d6) δ = 7.80 (1H,
2-amino-4-(3-bromophenyl)-4,8-dihydro-6-(hydro-
xymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile
(4d): White solid; m.p. 238–240 °C; IR (KBr, ν): 3420,
3323, 3208, 2911, 2863, 2196, 1642, 1593, 1408,
1226 cm–1. 1H NMR (400 MHz, DMSO-d6) δ = 7.67 – 7.60
(2H, m, Ar-H), 7.46 (1H, t, J = 8 Hz, Ar-H), 7.39–7.40(3H,
m, NH2, Ar-H), 6.43 (1H, s, H-7), 5.78 (1H, t, J = 6.0 Hz,
OH), 4.95 (1H, s, H-4), 4.30 (1H, dd, J = 6.0. 16.0 Hz,
CH2), 4.22 (1H, dd, J = 6.0. 16.0 Hz, CH2) ppm. 13C NMR
(100 MHz, DMSO-d6) δ = 176.9, 169.4, 168.3, 159.1,
143.6, 142.9, 136.0, 131.6, 130.7, 130.3, 127.2, 122.0,
119.1, 114.3, 59.1, 55.2 ppm.
d, J = 2.4 Hz, Ar-H), 7.61 (1H, dd, J = 2.4 8.4 Hz, Ar-H),
7.55 (1H, d, J = 8.4 Hz, Ar-H), 7.46 (2H, s, NH2), 6.46
(1H, s, H-7) 5.80 (1H, t, J = 6.0 Hz, OH), 5.40 (1H, s, H-
4), 4.31 (1H, dd, J = 6.0 15.6 Hz, CH2), 4.23 (1H, dd, J =
6.0 15.6 Hz, CH2) ppm. 13C NMR (100 MHz, DMSO-d6)
δ = 169.8, 168.7, 159.9, 148.0, 137.6, 137.1, 134.3,
133.8, 133.0, 129.7, 128.9, 119.5, 111.7, 59.5, 56.1,
38.4 ppm
Methyl
4-(2-amino-3-cyano-4,8-dihydro-6-(hydro-
xymethyl)-8-oxopyrano[3,2-b]pyran-4-yl)benzoate (4i)
(new compound): White solid; m.p. 249–250 °C; IR (KBr,
ν): 3303, 3187, 3077, 2948, 2870, 2192, 1728, 1635, 1597,
1
2-amino-4-(3-nitrophenyl)-4,8-dihydro-6-(hydro-
xymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile (4e):
Yellow solid; m.p. 255–257 °C; IR (KBr, ν): 3529, 3377,
3318, 3207, 3082, 2867, 2188, 1643, 1592, 1531, 1438,
1441, 1274, 1208 cm–1. H NMR (400 MHz, DMSO-d6)
δ = 8.10 (2H, d, J = 8.4 Hz, Ar-H), 7.57 (2H, d, J = 8.4 Hz,
Ar-H), 7.43 (2H, s, NH2), 6.44 (1H, s, H-7), 5.79 (1H, t,
J = 6.0 Hz, OH), 5.06 (1H, s, H-4), 4.30 (1H, dd, J = 6.0