A. Z. Halimehjani and N. Keshavarzi
Vol 000
1023, 755, 665, 582 cmÀ1; 1H NMR (500 MHz, DMSO-d6)
δ 0.99 (s, 3H), 1.05 (s, 2H), 2.02 (d, J = 16.0 Hz, 1H), 2.23
(d, J = 15.9 Hz, 1H), 2.32 (d, J = 17.2, 1H), 2.53 (d,
J = 17.5 Hz, 1H), 5.06 (s, 1H), 6.75–6.78 (m, 1H),
6.94–7.18 (m, 7H), 10.42 (brs, 1H) ppm; 13C NMR
(125 MHz, DMSO-d6) δ 26.7, 28.1, 29.6, 32.0, 41.1,
50.9, 111.2, 115.1, 115.6, 115.7, 119.2, 119.4, 121.0,
124.6, 126.1, 127.2, 128.8, 129.8, 150.1, 165.1, 196.2
(C═O) ppm; Anal. Calcd for C21H20O3: C, 78.73; H,
3,4-Dihydro-9-(1H-indol-3-yl)-3,3-dimethyl-2H-xanthen-
1(9H)-one (5h). Yellow crystalline solid (0.305 g, 89%
yield); mp 199–201 °C; IR (KBr) ν 3349, 3050, 2952,
1722, 1637, 1581, 1485, 1456, 1422, 1233, 1178, 1144,
1124, 1095, 1012, 755 cmÀ1 1H NMR (500 MHz,
;
CDCl3) δ 0.98 (s, 3H), 1.13 (s, 3H), 2.22 (AB
,
quartet
J = 16.2 Hz, 2H), 2.54 (AB quartet, J = 17.4 Hz, 2H), 5.34
(s, 1H), 6.97–7.02 (m, 2H), 7.08–7.23 (m, 5H), 7.27 (m,
1H), 7.41 (d, J = 8.0 Hz, 1H), 8.11 (brs, 1H) ppm; 13C
NMR (125 MHz, CDCl3) δ 28.1, 29.5, 29.9, 32.5, 41.9,
51.3, 111.6, 113.1, 116.7, 119.5, 119.7, 120.9, 122.0,
122.8, 125.3, 125.7, 126.1, 127.8, 130.6, 136.9, 139.8,
150.0, 197.8 (C═O) ppm; Anal. Calcd for C23H21NO2:
C, 80.44; H, 6.16, N, 4.08; Found: C, 80.24; H, 5.98; N,
6.29; Found: C, 78.80; H, 5.99%.
3,4-Dihydro-9-(4-hydroxy-2-oxo-2H-chromen-3-yl)-3,3-
dimethyl-2H-xanthen-1(9H)-one (5e). White solid (0.335 g,
86% yield); mp 265–267 °C; IR (KBr) ν 3224, 3010, 2955,
1
1673, 1623, 1493, 1384, 1236, 1066, 898, 753 cmÀ1; H
NMR (500 MHz; CDCl3) δ 1.08 (s, 3H), 1.18 (s, 3H),
2.39 (AB quartet, J = 17.1 Hz, 2H), 2.55 (d, J = 17.6 Hz,
1H), 2.66 (d, J = 17.6 Hz, 1H), 5.09 (s, 1H), 7.04–7.06
(m, 2H), 7.10 (d, J = 8.2 Hz, 1H), 7.20–7.23 (m, 2H),
7.28–7.32 (m, 1H), 7.48–7.51 (m, 1H), 8.03 (dd, J = 7.8
and 1.4 Hz, 1H), 11.08 (brs, 1H) ppm; 13C NMR
(125 MHz, CDCl3) δ 27.1, 28.5, 29.2, 32.3, 41.7, 49.9,
109.1, 109.9, 116.0, 116.2, 117.0, 122.3, 123.7, 124.2,
124.9, 128.2, 128.5, 131.6, 151.2, 153.0, 160.9, 161.1,
170.1, 201.3 (C═O) ppm; Anal. Calcd for C24H20O5: C,
3.88%.
2-Hydroxy-12-(2-hydroxyphenyl)-8,10-dimethyl-8H-
benzo[5,6]chromeno[2,3-d]pyrimidine-9,11(10H,12H)-dione
(5i). Yellow crystalline solid (0.350 g, 87% yield); mp
224–226 °C; IR (KBr) ν 3394, 3278, 2964, 1700, 1643,
1490, 1438, 1273, 1327, 1039, 834, 766, 596 cmÀ1; H
1
NMR (500 MHz, DMSO-d6) δ 3.08 (s, 3H), 3.51 (s, 3H),
5.76 (s, 1H), 6.66 (d, J = 8.6 Hz, 1H), 6.91–7.03 (m,
4H), 7.22–7.24 (m, 1H), 7.46 (d, J = 8.7 Hz, 1H), 7.60
(d, J = 8.7 Hz, 1H), 7.86 (s, 1H), 9.29 (s, 1H), 9.63 (s,
1H) ppm; 13C NMR (125 MHz, DMSO-d6) δ 27.9, 29.3,
30.0, 88.3, 105.4, 115.2, 115.8, 116.0, 121.7, 123.2,
124.6, 125.5, 127.9, 128.6, 128.9, 130.2, 135.3, 149.6,
150.6, 153.6, 154.2, 156.7 (C═O), 161.5 (CO) ppm;
Anal. Calcd for C23H18N2O5: C, 68.65; H, 4.51; N, 6.96;
74.21; H, 5.19; Found: C, 74.08; H, 4.89%.
9,10-Dihydro-2-hydroxy-12-(2-hydroxyphenyl)-9,9-dimethyl-
8H-benzo[a]xanthen-11(12H)-one (5f).
White crystalline
solid (0.350 g, 90% yield); mp 274–276 °C; IR (KBr) ν
3233, 2953, 1621, 1588, 1484, 1399, 1232, 1031, 836,
1
758 cmÀ1; H NMR (500 MHz, CDCl3 + DMSO-d6) δ
Found: C, 68.30; H, 4.51; N, 7.35%.
4,5-Dihydro-5-(4-hydroxy-2-oxo-2H-chromen-3-yl)-1,3-
dimethyl-1H-chromeno[2,3-d]pyrimidine-2,4(3H,10H)-dione
(5j). White crystalline solid (0.260 g, 64% yield); mp
0.80 (s, 3H), 0.97 (s, 3H), 2.13–2.24 (AB
,
quartet
J = 16.5 Hz, 2H), 2.41 (s, 2H), 5.44 (s, 1H), 6.43–6.49
(m, 2H), 6.73–6.96 (m, 4H), 6.94 (d, J = 8.8 Hz, 1H),
7.28 (d, J = 8.8 Hz, 1H), 7.48 (d, J = 8.8 Hz, 1H), 9.13
(brs, 2H) ppm; 13C NMR (125 MHz, CDCl3 + DMSO-
d6) δ 26.8, 27.8, 28.9, 32.1, 41.3, 50.1, 105.4, 113.1,
113.7, 115.6, 117.6, 118.1, 120.8, 125.8, 127.4, 128.4,
128.7, 129.7, 132.2, 132.7, 148.2, 152.9, 156.4, 166.7,
199.9 (C═O) ppm; Anal. Calcd for C25H22O4: C, 77.70;
285–287 °C; IR (KBr) ν 3275, 3065, 2957, 1719, 1673,
1580, 1484, 1451, 1396, 1240, 1112, 751, 757 cmÀ1; H
1
NMR (500 MHz, CDCl3) δ 3.40 (s, 3H), 3.64 (s, 3H),
5.31 (s, 1H), 7.13–7.33 (m, 6H), 7.50 (m, 1H), 8.03
(d, J = 7.8 Hz, 1H), 11.48 (s, 1H) ppm; 13C NMR
(125 MHz, DMSO-d6) δ 28.0, 29.3, 32.7, 91.4, 114.2,
116.4, 116.5, 116.6, 116.7, 122.9, 124.4, 125.8, 128.6,
128.9, 132.5, 149.7, 150.5, 152.5, 153.9, 161.7 (CO),
166.6 (CO), 186.3 (─COO) ppm; Anal. Calcd for
C22H16N2O6: C, 65.34; H, 3.99; N, 6.93; Found: C,
H, 5.74; Found: C, 77.55; H, 5.74%.
9,10-Dihydro-6-hydroxy-12-(2-hydroxyphenyl)-9,9-dimethyl-
8H-benzo[a]xanthen-11(12H)-one (5g).
White solid
(0.328 g, 85% yield); mp 250–252 °C; IR (KBr) ν 3422,
65.55; H, 3.87; N, 6.98%.
3201, 2951, 2927, 1587, 1458, 1382, 1220, 858,
4-Hydroxy-7-(2-hydroxyphenyl)-9,11-dimethyl-7H-
benzo[7,8]chromeno[2,3-d]pyrimidine-8,10(9H,11H)-dione
(5k). White solid (0.286 g, 71% yield); mp 275–278 °C;
745 cmÀ1 1H NMR (500 MHz, DMSO-d6) δ 0.90
;
(s, 3H), 1.07 (s, 3H), 2.28 (AB quartet, J = 16.6 Hz, 2H),
2.61 (s, 2H), 5.68 (s, 1H), 6.53–6.62 (m, 2H), 6.89–6.91
(m, 2H), 7.10–7.13 (m, 1H), 7.19–7.22 (m, 2H), 7.49–
7.52 (m, 2H), 9.14 (brs, 2H) ppm; 13C NMR (125 MHz,
DMSO-d6) δ 30.7, 32.9, 33.4, 36.4, 44.9, 54.7, 113.7,
117.3, 120.3, 123.7, 123.9, 127.8, 127.9, 129.5, 129.9,
130.8, 131.7, 134.3, 135.8, 143.9, 145.2, 149.7, 157.9,
168.7, 200.8 (C═O) ppm; Anal. Calcd for C25H22O4: C,
77.70; H, 5.74; Found: C, 77.65; H, 5.40%.
IR (KBr) ν 3430, 3321, 2961, 1928, 1698, 1631, 1482,
1239, 760 cmÀ1; H NMR (500 MHz, DMSO-d6) δ 3.13
1
(s, 3H), 3.51 (s, 3H), 5.67 (s, 1H), 6.79 (d, J = 7.5 Hz,
1H), 7.01 (d, J = 8.7 Hz, 1H), 7.11 (t, J = 7.2 Hz, 1H),
7.23–7.34 (m, 4H), 7.50 (d, J = 8.7 Hz, 1H), 7.66
(d, J = 8.5 Hz, 1H), 9.57 (s, 1H), 9.92 (s,1H) ppm; 13C
NMR (125 MHz, DMSO-d6) δ 28.2, 29.4, 32.7, 89.0,
108.5, 113.3, 114.5, 116.8, 124.9, 125.2, 125.7, 125.8,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet