Paper
RSC Advances
133.44, 132.35, 131.91, 130.44, 129.68, 128.81, 127.42, 125.69,
117.58, 113.61, 113.29, 105.66, 88.58, 55.69, 33.62, 28.95, 27.68
ppm; IR (KBr) nmax, cm21 = 3200, 1670, 1638, 1554, 1245; MS
(ESI) m/z Calcd. for C24H20N2O5: 416.14, Found: 453.1 [M+ + H],
455.1 [M+ + H + 2]; Anal. Calcd. for C24H20N2O5: C, 69.22; H,
4.84; N, 6.73; Found: C, 69.25; H, 4.81; N, 6.72; UV (2 6 1024 M
solution in DMSO) lmax (e) : 324 nm (0.273 6 104 L mol21
cm21), 337 (0.336 6 104 L mol21 cm21).
141.21, 135.47, 132.08, 130.35, 129.16, 128.75, 128.02, 125.75,
117.57, 115.22, 113.33, 105.55, 90.27, 35.17, 28.91, 27.73,
20.52; IR (KBr) nmax, cm21 = 3170, 1658, 1602, 1492, 1196; MS
(ESI) m/z Calcd. for C24H20N2O4: 400.14, Found: 401.20 [M+ +
H]; Anal. Calcd. for C24H20N2O4: C, 71.99; H, 5.03; N, 7.00;
Found: C, 71.96; H, 5.01; N, 6.98; UV (2 6 1024 M solution in
DMSO) lmax (e) : 323 nm (0.203 6 104 L mol21 cm21), 337
(0.250 6 104 L mol21 cm21).
2-Hydroxy-12-(2-methoxyphenyl)-8,12-dihydro-8,10-dimethyl-
9H-naphtho[19,29 : 5,6]pyrano[2,3-d]pyrimidine-9,11-(10H)-
dione (3f, C24H20N2O5)
2-Hydroxy-12-(4-nitrophenyl)-8,12-dihydro-8,10-dimethyl-
9H-naphtho[19,29 : 5,6]pyrano[2,3-d]pyrimidine-9,11-(10H)-
dione (3i, C23H17N3O6)
White solid; Yield = 82%; M.p.: .300 uC (decom.); Rf 0.30
(petroleum ether : EtOAc, 60 : 40 v/v); 1H NMR (400 MHz,
DMSO-d6): d = 9.82 (s, 1H, OH), 7.76–7.70 (m, 2H, Ar), 7.40 (s,
1H, Ar), 7.32–7.31 (m, 1H, Ar), 7.26 (d, J = 8.8 Hz, 1H, Ar), 7.09–
7.05 (m, 1H, Ar), 6.99–6.97 (m, 1H, Ar), 6.87–6.79 (m, 2H, Ar),
5.59 (s, 1H, ArC_H_), 3.71 (s, 3H, OC_H_3), 3.50 (s, 3H, NC_H_3),
3.14 (s, 3H, NC_H_3) ppm; 13C NMR (100 MHz, CDCl3): d =
160.81, 156.60, 152.46, 151.06, 147.32, 141.04, 132.44, 132.32,
132.11, 130.34, 129.63, 129.57, 128.25, 127.22, 125.66, 117.49,
114.27, 113.31, 105.79, 89.05, 55.98, 33.94, 28.95, 27.76 ppm;
IR (KBr) nmax, cm21 = 3160, 1660, 1630, 1550, 1240; MS (ESI) m/
z Calcd. for C24H20N2O5: 416.14, Found: 417.12 [M+ + H]; Anal.
Calcd. for C24H20N2O5: C, 69.22; H, 4.84; N, 6.73; Found: C,
69.24; H, 4.82; N, 6.71; UV (2 6 1024 M solution in DMSO)
lmax (e) = 325 nm (0.239 6 104 L mol21 cm21), 337 (0.298 6
104 L mol21 cm21).
Cream solid; Yield = 89%; M.p.: .300 uC (decom.); Rf 0.45
(petroleum ether : EtOAc, 50 : 50 v/v); 1H NMR (400 MHz,
DMSO-d6): d 9.99 (s, 1H, OH), 8.07 (d, J = 8.6 Hz, 2H, Ar), 7.86
(d, J = 8.7 Hz, 1H, Ar), 7.78 (d, J = 8.6 Hz, 1H, Ar), 7.56 (d, J = 8.7
Hz, 2H, Ar), 7.34 (d, J = 8.7 Hz, 1H, Ar), 7.10 (s, 1H, Ar), 6.99–
6.97 (m, 1H, Ar), 5.53 (s, 1H, ArC_H_), 3.46 (s, 3H, NC_H_3), 3.12
(s, 3H, NC_H_3) ppm; 13C NMR (100 MHz, DMSO-d6): d 161.11,
156.88, 152.45, 151.40, 150.08, 147.26, 146.14, 131.97, 130.53,
129.91, 129.56, 125.80, 123.49, 117.87, 113.65, 133.29, 105.50,
88.89, 35.79, 29.03, 27.90 ppm; IR (KBr) nmax, cm21 = 3241,
1660, 1554, 1245; MS (ESI) m/z Calcd. for C23H17N3O6: 431.11
Found: 432.11 [M+ + H]; Anal. Calcd. for C23H17N3O6 :C, 64.04;
H, 3.97; N, 9.74; Found: C, 64.06; H, 3.96; N, 9.72; UV (2 6
1024 M solution in DMSO) lmax (e) : 321 nm (0.223 6 104 L
mol21 cm21), 336 (0.608 6 104 L mol21 cm21).
2-Hydroxy-12-(3-nitrophenyl)-8,12-dihydro-8,10-dimethyl-
9H-naphtho[19,29 : 5,6]pyrano[2,3-d]pyrimidine-9,11-(10H)-
dione (3j, C23H17N3O6)
2-Hydroxy-12-(3,4,5-trimethoxyphenyl)-8,12-dihydro-8,10-
dimethyl-9H-naphtho[19,29 : 5,6]pyrano[2,3-d]pyrimidine-9,11-
(10H)-dione (3g, C26H24N2O7)
Cream solid; Yield = 83%; M.p.: .300 uC (decom.); Rf 0.35
(petroleum ether : EtOAc, 50 : 50 v/v); 1H NMR (400 MHz,
DMSO-d6): d = 9.97 (s, 1H, OH), 8.12 (s, 1H, Ar), 7.98 (d, J = 8.8
Hz, 1H, Ar), 7.88 (d, J = 8.7 Hz, 1H, Ar), 7.78 (d, J = 8.8 Hz, 1H,
Ar), 7.70 (d, J = 7.3 Hz, 1H, Ar), 7.51–7.48 (m, 1H, Ar), 7.37 (d, J
= 8.8 Hz, 1H, Ar), 7.09 (s, 1H, Ar), 6.98–6.96 (m, 1H, Ar), 5.55 (s,
1H, ArC_H_), 3.46 (s, 3H, NC_H_3), 3.12 (s, 3H, NC_H_3) ppm; 13C
NMR (100 MHz, DMSO-d6): d = 161.15, 156.86, 152.39, 150.05,
147.57, 147.38, 145.96, 134.96, 131.86, 130.52, 129.92, 125.77,
121.78, 117.77, 113.55, 113.29, 105.38, 88.97, 35.61, 28.97,
27.80 ppm; IR (KBr) nmax, cm21 = 3120, 1668, 1620, 1358, 1203;
MS (ESI) m/z Calcd. for C23H17N3O6: 431.11, Found: 432.18 [M+
+ H]; Anal. Calcd. for C23H17N3O6: C, 64.04; H, 3.97; N, 9.74;
Found: C, 64.06; H, 3.96; N, 9.72; UV (2 6 1024 M solution in
DMSO) lmax (e) = 323 nm (0.443 6 104 L mol21 cm21), 337
(0.457 6 104 L mol21 cm21).
White solid; Yield = 76%; M.p.: .300 uC (decom.); Rf 0.30
(petroleum ether : EtOAc, 60 : 40 v/v); 1H NMR (400 MHz,
DMSO-d6): d = 9.96 (s, 1H, OH), 7.84 (d, J = 8.8 Hz, 1H, Ar), 7.79
(d, J = 8.8 Hz, 1H, Ar), 7.34 (d, J = 8.8 Hz, 1H, Ar), 7.25 (s, 1H,
Ar), 7.01 (dd, 1,2J = 2.2 Hz, 1,3J = 8.6 Hz, 1H, Ar), 6.52–6.47 (m,
2H, Ar), 5.37 (s, 1H, ArC_H_), 3.63 (s, 6H, 2 6 OC_H_3), 3.53 (s,
3H, OC_H_3), 3.47 (s, 3H, NC_H_3), 3.16 (s, 3H, NC_H_3); 13C NMR
(100 MHz, DMSO-d6): d = 161.26, 156.61, 152.51, 152.42,
150.13, 147.35, 139.71, 136.13, 132.18, 130.41, 129.28, 125.74,
117.67, 115.01, 113.35, 105.59, 90.08, 59.82, 55.80, 35.78,
28.96, 27.82; IR (KBr) nmax, cm21 = 3190, 1640, 1615, 1412,
1220; MS (ESI) m/z Calcd. for C26H24N2O7: 476.48, Found:
477.23 [M+ + H]; Anal. Calcd. for C26H24N2O7 C, 65.54; H, 5.08;
N, 5.88; Found: C, 65.52; H, 5.06; N, 5.85; UV (2 6 1024
M
solution in DMSO) lmax (e) = 323 nm (0.307 6 104 L mol21
cm21), 337 (0.383 6 104 L mol21 cm21).
2-Hydroxy-12-(2-nitrophenyl)-8,12-dihydro-8,10-dimethyl-
9H-naphtho[19,29 : 5,6]pyrano[2,3-d]pyrimidine-9,11-(10H)-
dione (3k, C23H17N3O6)
2-Hydroxy-12-(4-methylphenyl)-8,12-dihydro-8,10-dimethyl-
9H-naphtho[19,29 : 5,6]pyrano[2,3-d]pyrimidine-9,11-(10H)-
dione (3h, C24H20N2O4)
Cream solid; Yield = 89%; M.p.: .300 uC (decom.); Rf 0.30
(petroleum ether : EtOAc, 50 : 50 v/v); 1H NMR (400 MHz,
DMSO-d6): d = 9.95 (s, 1H, OH), 8.11 (s, 1H, Ar), 7.97 (d, J = 8.8
Hz, 1H, Ar), 7.86 (d, J = 8.7 Hz, 1H, Ar), 7.76 (d, J = 8.8 Hz, 1H,
Ar), 7.70 (d, J = 7.3 Hz, 1H, Ar), 7.51–7.48 (m, 1H, Ar), 7.32 (d, J
= 8.8 Hz, 1H, Ar), 7.10 (s, 1H, Ar), 6.97–6.96 (m, 1H, Ar), 5.60 (s,
1H, ArC_H_), 3.47 (s, 3H, NC_H_3), 3.11 (s, 3H, NC_H_3) ppm; 13C
NMR (100 MHz, DMSO-d6): d = 161.14, 156.82, 152.38, 150.01,
White solid; Yield = 82%; M.p.: .300 uC (decom.); Rf 0.40
(petroleum ether : EtOAc, 60 : 40 v/v); 1H NMR (400 MHz,
DMSO-d6): d = 9.92 (s, 1H, OH), 7.82 (d, J = 9.5 Hz, 1H, Ar), 7.77
(d, J = 8.8 Hz, 1H, Ar), 7.33 (d, J = 8.8 Hz, 1H, Ar), 7.18–7.14 (m,
3H, Ar), 6.99 (d, J = 8.0 Hz, 3H, Ar), 5.36 (s, 1H, ArC_H_), 3.47 (s,
3H, NC_H_3), 3.13 (s, 3H, NC_H_3), 2.15 (s, 3H, CH3); 13C NMR
(100 MHz, DMSO-d6): d = 161.10, 156.56, 150.09, 147.22,
RSC Adv.
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