N. G. Khaligh
-
1 l
6
28 cm ; H NMR (600 MHz, DMSO-d ) d = 7.61 (s, 2H), 7.13 (t, J = 1.2 Hz,
6
2
H), 6.88 (t, J = 1.02 Hz, 2H), 3.96 (t, J = 6.5 Hz, 4, N–CH ), 1.60–1.63 (m, 4, –
2
13
CH CH –) ppm; C NMR (150 MHz, DMSO-d ) d = 28.14, 45.74, 119.68,
2
2
6
1
28.86, 137.66 ppm; MS (ESI): calcd. for C H N O S : 351.0433, found:
51.2512.
10 15 4 6 2
3
Physical and spectral data of new products
9
-(Furan-2-yl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione
(
3f) mp. 164–166 °C; FTIR (KBr) mmax=3064, 2887, 1730, 1670, 1606, 1465,
-
1 1
1
J = 7.6 Hz, 1H), 6.18–6.16 (m, 2H), 4.94 (s, 1H), 2.43 (s, 4H), 2.23 (2, 4H), 1.08 (s,
350, 1200, 1182, 1138, 1013 cm ; H NMR (400 MHz, CDCl ) d = 7.13 (d,
3
1
3
6
H), 1.01 (s, 6H) ppm; C NMR (100 MHz, CDCl ) d = 192.4, 164.8, 142.4,
3
138.6, 116.2, 115.2, 111.2, 50.9, 40.1, 32.3, 29.0, 28.2 ppm; MS (ESI):
?
m/z = [M ? H] 341.
9
-(Thiophene-2-yl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione
(
3g) mp. 147–149 °C; FTIR (KBr) mmax=3140, 2924, 1715, 1650, 1618, 1462,
-
1 1
1
J = 7.4 and 1.6 Hz, 1H), 6.83 (d, J = 7.6 Hz, 1H), 6.56 (d, J = 7.4 Hz, 1H), 4.61 (s,
346, 1208, 1170, 1118, 1010 cm ; H NMR (400 MHz, CDCl ) d = 7.31 (dd,
3
1
H), 2.41 (s, 4H), 2.11 (s, 4H), 1.19 (s, 6H), 1.18 (s, 6H) ppm; C NMR (100 MHz,
3
1
CDCl ) d = 196.2, 162.8, 148.2, 126.7, 125.4, 123.4, 115.3, 50.8, 40.9, 32.2, 29.3,
3
?
7.4 ppm; MS (ESI): m/z = [M ? H] 357.
2
9
1
2
1
1
-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-3,3-dimethyl-2,3,4,9-tetrahydro-
H-xanthen-1-one (3i) m.p. 190 °C (dec.); FTIR (KBr) mmax=3181, 2955, 2932,
-
1 1
870, 1645, 1594, 1374, 1232 cm ; H NMR (400 MHz, CDCl ) d = 10.48 (s,
3
H), 7.18–7.05 (m, 4H), 2.59–2.33 (m, 6H), 4.68 (s, 1H), 1.97 (d, 2H, J = 4.8 Hz),
1
.14 (s, 3H), 1.04 (s, 3H), 1.01 (s, 6H) ppm; C NMR (100 MHz, CDCl3)
3
d = 201.0, 196.5, 170.7, 169.1, 151.1, 128.0, 127.5, 124.6, 124.3, 118.3, 115.7,
11.1, 50.6, 49.9, 43.2, 41.6,32.3, 30.9, 29.9, 29.2, 27.8, 27.2, 26.5 ppm; MS (ESI):
1
m/z = [M ? H] 367.19.
?
9
-(2,4-Dimethyl-phenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-
dione (3j) mp. 210–212 °C; FTIR (KBr) mmax=2957, 1660, 1465, 1350, 1200,
-
1 1
1
1
2
162, 1138, 1013, 854 cm ; H NMR (400 MHz, CDCl ) d = 7.34 (d, J = 8.4 Hz,
3
H), 6.42 (d, J = 9.2 Hz, 1H), 6.32 (s, 1H), 4.77 (s, 1H), 2.74 (s, 3H), 2.47 (s, 3H),
.43 (d, J = 17.6 Hz, H CH , 2H), 2.35 (d, J = 17.6 Hz, H CH , 2H), 2.21 (d,
a
b
a
b
J = 16.4 Hz, H CH , 2H), 2.16 (d, J = 16.4 Hz, H CH , 2H), 1.09 (s, 6H), 0.95 (s,
a
b
a
b
1
3
6
1
H) ppm; C NMR (100 MHz, CDCl ) d = 196.4, 161.9, 159.6, 158.4, 132.7,
3
23.4, 116.2, 50.9, 40.1, 32.3, 29.0, 28.2, 21.0, 19.4 ppm; MS (ESI):
?
m/z = [M ? H] 378.
9
,9-Dimethyl-12-thiophen-2yl-8,9,10,12-tetrahydro-benzo[a]xanthene-11-one (3v) m.p.
-
1
1
1
75–177 °C; FTIR (KBr) mmax=2920, 1585,1371,1216,1188 cm
;
H NMR
(
(
400 MHz, CDCl ) d = 8.14 (d, J = 8.8 Hz, 1H), 7.82–7.76 (m, 2H), 7.54–7.50
3
m, 1H), 7.44–7.40 (m, 1H), 7.33 (d, J = 8 Hz, 1H), 6.97–6.95 (m, 1H),
1
23