9968
M.K. Parai et al. / Tetrahedron 64 (2008) 9962–9976
762 cmꢀ1
.
1H NMR (200 MHz, CDCl3):
d
7.25 (dd, 1H, J1¼4.7 Hz,
(200 MHz, CDCl3):
d
8.34 (s, 1H, ArH), 8.10 (d, 1H, J¼1 Hz, ArH), 7.75
J2¼1.0 Hz, ArH), 7.02–6.91 (m, 3H, ArH), 6.39 (d, 1H, J¼2.5 Hz, ArH),
6.31 (dd, 1H, J1¼8.5 Hz, J2¼2.5 Hz, ArH), 5.82 (s, 1H, 3-H), 5.78 (s, 1H,
CHOH), 3.71 (s, 3H, OCH3), 2.35 (br s, 1H, CHOH), 1.46 (s, 6H, 2-CH3).
(d,1H, J¼7.6 Hz, ArH), 7.51 (t,1H, J¼7.9 Hz, ArH), 6.95 (d,1H, J¼8.5 Hz,
ArH), 6.39 (d, 1H, J¼2.5 Hz, ArH), 6.30 (dd, 1H, J1¼8.5 Hz, J2¼2.5 Hz,
ArH), 5.70 (s,1H, 3-H), 5.62 (s,1H, CHOH), 3.72 (s, 3H, OCH3), 2.42 (br
13C NMR (50 MHz, CDCl3):
d
160.9, 154.9, 146.6, 133.7, 127.3, 126.0,
s, 1H, CHOH), 1.46 (s, 6H, 2-CH3). 13C NMR (50 MHz, CDCl3):
d 161.2,
125.0, 113.6, 107.0, 102.7, 76.7, 71.2, 69.0, 55.6, 28.2. MS (FAB): m/z
(%): 302 (40, [Mþ]), 287 (100, [MþꢀCH3]), 285 (60, [MþꢀOH]). Anal.
Calcd for C17H18O3S: C, 67.52; H, 6.00. Found: C, 67.46; H, 6.09.
155.2, 148.8, 144.2, 133.2, 129.8, 127.1, 125.2, 123.1, 122.2,113.0, 107.1,
103.0, 76.5, 73.0, 55.6, 28.1. MS (FAB): m/z (%): 341 (45, [Mþ]), 326
(100, [MþꢀCH3]), 324 (20, [MþꢀOH]). Anal. Calcd for C19H19NO5: C,
66.85; H, 5.61; N, 4.10. Found: C, 66.81; H, 5.68; N, 4.07.
3.2.10. Furan-2-yl-(7-methoxy-2,2-dimethyl-2H-chromen-4-yl)-
methanol 1j
3.2.15. 4-[Hydroxy-(7-methoxy-2,2-dimethyl-2H-chromen-4-yl)-
methyl]-benzonitrile 1o
Yield¼58% as a dark yellow oil; Rf¼0.5 (15% ethyl acetate in
hexane). IR (Neat): 3434, 2974, 1614, 1503, 1276, 1145, 746 cmꢀ1. 1H
Yield¼55% as a yellowoil; Rf¼0.5 (20% ethyl acetate in hexane). IR
NMR (200 MHz, CDCl3):
d
7.30 (s, 1H, ArH), 6.87 (d, 1H, J¼8.4 Hz,
(Neat): 3450, 2969, 1613, 1503, 1277, 1199, 1146, 760 cmꢀ1. 1H NMR
ArH), 6.33–6.20 (m, 3H, ArH), 6.12 (d, 1H, J¼3.2 Hz, ArH), 5.63 (s, 1H,
3-H), 5.59 (s, 1H, CHOH), 3.65 (s, 3H, OCH3), 2.48 (br s, 1H, CHOH),
(200 MHz, CDCl3):
d
7.52 (d, 2H, J¼8.2 Hz, ArH), 7.46 (d, 2H, J¼8.2 Hz,
ArH), 6.84 (d,1H, J¼8.5 Hz, ArH), 6.30 (d,1H, J¼2.4 Hz, ArH), 6.21 (dd,
1H, J1¼8.5 Hz, J2¼2.5 Hz, ArH), 5.54 (s, 1H, 3-H), 5.46 (s, 1H, CHOH),
3.63 (s, 3H, OCH3), 1.35 (s, 6H, 2-CH3). 13C NMR (50 MHz, CDCl3):
1.36 (s, 6H, 2-CH3). 13C NMR (50 MHz, CDCl3):
d 160.9, 155.1, 154.8,
142.8, 131.1, 125.5, 124.7, 113.8, 110.8, 108.2, 106.9, 102.7, 76.6, 66.9,
55.6, 28.1. MS (FAB): m/z (%): 286 (50, [Mþ]), 271 (100, [MþꢀCH3]),
269 (70, [MþꢀOH]). Anal. Calcd for C17H18O4: C, 71.31; H, 6.34.
Found: C, 71.40; H, 6.31.
d
161.1, 155.1, 147.5, 133.2, 132.7, 127.8, 127.1, 125.3, 119.1, 113.2, 111.7,
107.0, 102.9, 76.5, 73.2, 55.6, 28.0. MS (FAB): m/z (%): 321 (50, [Mþ]),
306 (100, [MþꢀCH3]), 304 (20, [MþꢀOH]). Anal. Calcd for
C
20H19NO3:C, 74.75;H, 5.96;N, 4.36. Found:C, 74.81;H, 5.93;N, 4.42.
3.2.11. 1-(7-Methoxy-2,2-dimethyl-2H-chromen-4-yl)-3-phenyl-
prop-2-en-1-ol 1k
3.2.16. (4-Isopropyl-phenyl)-(7-methoxy-2,2-dimethyl-2H-
chromen-4-yl)-methanol 1p
Yield¼52% as a yellow oil; Rf¼0.6 (15% ethyl acetate in hexane).
IR (Neat): 3430, 2928, 1612, 1277, 1146, 758 cmꢀ1
.
1H NMR
Yield¼65% as a yellow oil; Rf¼0.6 (15% ethyl acetate in hexane).
(200 MHz, CDCl3):
d
7.40–7.24 (m, 6H, ArH), 6.72 (d, 1H, J¼15.9 Hz,
IR (Neat): 3436, 2964, 1614, 1504, 1277, 1198, 1146, 1069, 758 cmꢀ1
.
CH]CHC6H5), 6.44–6.37 (m, 3H, ArH, CH]CHC6H5), 5.64 (s, 1H,
3-H), 5.23 (d, 1H, J¼5.9 Hz, CHOH), 3.74 (s, 3H, OCH3), 2.19 (br s, 1H,
1H NMR (200 MHz, CDCl3):
d
7.35 (d, 2H, J¼8.1 Hz, ArH), 7.25–7.15
(m, 2H, ArH), 6.92 (d, 1H, J¼8.5 Hz, ArH), 6.39 (d, 1H, J¼2.5 Hz, ArH),
6.29 (dd,1H, J1¼8.5 Hz, J2¼2.5 Hz, ArH), 5.72 (s, 1H, 3-H), 5.60 (s, 1H,
CHOH), 3.71 (s, 3H, OCH3), 2.88 {sept, 1H, CH(CH3)2}, 2.12 (br s, 1H,
CHOH), 1.47 (s, 6H, 2-CH3), 1.23 {d, 6H, J¼6.9 Hz, CH(CH3)2}. 13C
CHOH), 1.42 (s, 6H, 2-CH3). 13C NMR (50 MHz, CDCl3):
d 161.0, 155.0,
136.9,133.5,132.1,130.4,128.9,128.2,127.0,125.2,125.1,113.9,107.0,
102.8, 76.6, 71.8, 55.6, 28.1. MS (FAB): m/z (%): 322 (30, [Mþ]), 307
(100, [MþꢀCH3]), 305 (95, [MþꢀOH]). Anal. Calcd for C21H22O3: C,
78.23; H, 6.88. Found: C, 78.34; H, 6.81.
NMR (50 MHz, CDCl3): d 160.8, 154.9, 149.1, 139.4, 133.5, 127.4, 127.1,
125.3, 113.9, 106.8, 102.6, 73.1, 55.5, 34.2, 28.3, 24.3. MS (FAB): m/z
(%): 338 (20, [Mþ]), 323 (100, [MþꢀCH3]), 321 (30, [MþꢀOH]). Anal.
Calcd for C22H26O3: C, 78.07; H, 7.74. Found: C, 78.12; H, 7.71.
3.2.12. (4-Dimethylamino-phenyl)-(7-methoxy-2,2-dimethyl-
2H-chromen-4-yl)-methanol 1l
Yield¼59% as yellow solid; mp 90 ꢁC (dichloromethane); Rf¼0.4
3.2.17. (7-Methoxy-2,2-dimethyl-2H-chromen-4-yl)-naphthalen-
1-yl-methanol 1q
(15% ethyl acetate in hexane). IR (KBr): 2429, 2972, 1613, 1521, 1146,
757 cmꢀ1. 1H NMR (200 MHz, CDCl3):
d
7.20 (d, 2H, J¼8.8 Hz, ArH),
Yield¼54% as a yellow oil; Rf¼0.6 (15% ethyl acetate in hexane).
6.80 (d, 1H, J¼8.5 Hz, ArH), 6.61 (d, 2H, J¼8.8 Hz, ArH), 6.30 (d, 1H,
J¼2.5 Hz, ArH), 6.20 (dd, 1H, J1¼8.5 Hz, J2¼2.5 Hz, ArH), 5.69 (s, 1H,
3-H), 5.47 (s, 1H, CHOH), 3.63 (s, 3H, OCH3), 2.86 {s, 6H, N(CH3)2},
1.38 (s, 3H, 2-CH3), 1.18 (s, 3H, 2-CH3). 13C NMR (50 MHz, CDCl3):
IR (Neat): 3434, 2958, 1614, 1277, 1210, 1145, 1068, 759 cmꢀ1 1H
.
NMR (200 MHz, CDCl3):
d 8.45–8.36 (m, 1H, ArH), 8.04 (d, 1H,
J¼8.2 Hz, ArH), 7.91–7.81 (m, 2H, ArH), 7.58–7.45 (m, 3H, ArH), 6.96
(d, 1H, J¼8.2 Hz, ArH), 6.45–6.40 (m, 2H, ArH), 5.64 (s, 1H, 3-H), 5.59
(s, 1H, CHOH), 3.76 (s, 3H, OCH3), 2.15 (br s, 1H, CHOH), 1.35 (s, 6H,
2-CH3). MS (FAB): m/z (%): 346 (30, [Mþ]), 331 (100, [MþꢀCH3]),
329 (40, [MþꢀOH]). Anal. Calcd for C23H22O3: C, 79.74; H, 6.40.
Found: C, 79.65; H, 6.43.
d
160.8, 154.9, 144.6, 134.7, 129.9, 128.6, 125.2, 124.6, 113.0, 106.8,
102.5, 72.8, 55.5, 40.9, 30.1, 28.3. MS (FAB): m/z (%): 339 (40, [Mþ]),
322 (100, [MþꢀOH]). Anal. Calcd for C21H25NO3: C, 74.31; H, 7.42; N,
4.13. Found: C, 74.20; H, 7.45; N, 4.19.
3.2.13. (2-Chloro-phenyl)-(7-methoxy-2,2-dimethyl-2H-chromen-
4-yl)-methanol 1m
3.2.18. 1-(7-Methoxy-2,2-dimethyl-2H-chromen-4-yl)-
propan-1-ol 1r
Yield¼60% as a yellow oil; Rf¼0.4 (15% ethyl acetate in hexane).
Yield¼66% as a yellow oil; Rf¼0.5 (10% ethyl acetate in hexane).
IR (Neat): 3434, 2969, 1614, 1503, 1276, 1199, 1146, 759 cmꢀ1
.
1H
IR (Neat): 3467, 2968, 1613, 1503, 1276, 1146, 758 cmꢀ1 1H NMR
.
NMR (200 MHz, CDCl3):
d
7.39–7.29 (m, 2H, ArH), 7.17–7.12 (m, 2H,
(200 MHz, CDCl3):
d
7.05 (d, 1H, J¼8.7 Hz, ArH), 6.34–6.26 (m, 2H,
ArH), 6.83 (d, 1H, J¼8.5 Hz, ArH), 6.33–6.23 (m, 2H, ArH), 5.99 (s, 1H,
ArH), 5.61 (s, 1H, 3-H), 4.86 (s, 1H, CHOH), 3.67 (s, 3H, OCH3), 2.02–
1.95 (m, 2H, CH2CH3), 1.69 (br s, 1H, CHOH), 1.36 (s, 6H, 2-CH3), 0.89
3-H), 5.46 (s, 1H, CHOH), 3.64 (s, 3H, OCH3), 2.36 (br s, 1H, CHOH),
1.34 (s, 6H, 2-CH3). 13C NMR (50 MHz, CDCl3):
d
160.9, 154.9, 139.3,
(t, 3H, J¼7.5 Hz, CH2CH3). 13C NMR (50 MHz, CDCl3):
d 160.7, 154.8,
133.9, 132.5, 130.0, 129.7, 128.8, 127.6, 125.8, 124.6, 113.9, 107.0,
102.8, 76.9, 68.9, 55.6, 28.1. MS (FAB): m/z (%): 330 (20, [Mþ]), 315
(100, [MþꢀCH3]), 313 (15, [MþꢀOH]). Anal. Calcd for C19H19ClO3: C,
68.98; H, 5.79. Found: C, 69.11; H, 5.76.
135.0, 132.1, 131.3, 124.9, 114.2, 106.7, 102.5, 76.0, 55.6, 28.2, 21.5,
12.4. MS (FAB): m/z (%): 248 (50, [Mþ]), 233 (100, [MþꢀCH3]), 231
(25, [MþꢀOH]). Anal. Calcd for C15H20O3: C, 72.55; H, 8.12. Found: C,
72.62; H, 8.19.
3.2.14. (7-Methoxy-2,2-dimethyl-2H-chromen-4-yl)-
(3-nitro-phenyl)-methanol 1n
3.2.19. 1-(7-Methoxy-2,2-dimethyl-2H-chromen-4-yl)-
butan-1-ol 1s
Yield¼53% as a dark yellow oil; Rf¼0.5 (25% ethyl acetate in
Yield¼64% as a yellow oil; Rf¼0.5 (10% ethyl acetate in hexane).
hexane). IR (Neat): 3453, 1613, 1530, 1351, 1146, 759 cmꢀ1. 1H NMR
IR (Neat): 3487, 2965, 1613, 1503, 1272, 1199, 1159, 1127, 758 cmꢀ1
.