Month 2015
Green, Solvent-Free, Microwave-Assisted, High Yielding YbCl3 Catalyzed
Deprotection of THP/MOM/Ac/Ts Ethers of Chalcone Epoxide and 2′-Aminochalcone
2H), 7.01 (d, J=9Hz, 2H), 4.66 (t, J=3Hz, 2H), 4.14 (tt,
J=11, 3Hz, 1H), 2.22–2.85 (m, 2H), 2.04 (s, br, D2O
exchangeable, 1H), 1.73–1.84 (m, 2H). 13C-NMR
(125MHz, CDCl3, ppm): δ 188.8, 166.7, 164.6, 144.6,
143.7, 140.8, 134.5, 134.3, 131.2, 130.0, 128.7, 127.7,
126.5, 125.9, 121.6, 115.9, 78.0, 77.7, 69.4, 40.0. IR
(KBr, cmÀ1): 3434, 3010, 2922, 2843, 1734, 1626, 1456,
1256, 1069, 808.8. HRMS (ESIMS): for C26H22ClFNaO3
763. GC–MS (m/z): 257 [M+, C15H12ClNO], 259 [M+ 2]+
(Supporting Information).
Acknowledgments. Financial support from DST and BRNS and
award of JRF to S.K. and N.K. by the CSIR and I.P. by the UGC,
New Delhi, India, are gratefully acknowledged.
(M+Na)+ Anal. Calcd 459.1139; found 459.1150.
(E)-1-(4-Bromophenyl)-3-(4-(6-(4-bromophenyl)-4-
hydroxytetrahydro-2H-pyran-2-yl)phenyl)prop-2-en-1-one (25a).
REFERENCES AND NOTES
[1] Hajipour, A. R.; Kargosha, M.; Ruoho, A. E. Synth Comm
2009, 39, 1084.
1H-NMR (500MHz, CDCl3, ppm): δ 7.88 (d, J=8Hz,
2H), 7.82 (d, J= 8.5Hz, 2H), 7.78 (s, 1H), 7.61–7.66 (m,
4H), 7.47 (s, 1H), 7.35 (d, J=8Hz, 2H), 7.31–7.32 (m,
2H), 4.45 (d, J=32, 11.5Hz, 2H), 4.07 (tt, J= 10.5, 3Hz,
1H), 2.30–2.35 (m, 2H), 2.20 (s, br, D2O exchangeable,
1H), 1.77–1.86 (m, 2H). 13C-NMR (125 MHz, CDCl3,
ppm): δ 189.8, 143.7, 140.7, 135.4, 134.4, 134.1, 129.8,
129.2, 128.5, 128.4, 127.8, 127.5, 126.2, 125.7, 122.0, 77.8,
77.4, 67.2, 39.8. IR (KBr, cmÀ1): 3454, 2961, 2878, 1651,
1541, 1091, 801. HRMS (ESIMS): for C26H22Br2NaO3 (M
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+Na)+ Anal. Calcd 562.9833; found 562.9853.
2-(4-(4-Hydroxy-6-phenyltetrahydro-2H-pyran-2-yl)phenyl)-
4H-chromen-4-one (26a). 1H-NMR (500 MHz, CDCl3, ppm):
δ 7.74 (d, J= 8 Hz, 2H), 7.37 (dd, J=6, 3Hz, 2H), 7.27 (d,
J= 8.5 Hz, 2H), 7.17–7.21 (m, 3H), 7.15 (d, J=8.5 Hz, 2H),
6.92 (s, 1H), 6.79 (dd, J=6.5, 3Hz, 2H), 4.40 (t, J=11.5Hz,
2H), 3.90 (tt, J = 11, 3 Hz, 1H), 2.15–2.22 (m, 2H),
1.68–1.77 (m, 2H). 13C-NMR (125 MHz, CDCl3, ppm):
δ 190.0, 163.0, 156.0, 139.8, 135.5, 134.1, 131.6, 129.9,
129.3, 128.6, 128.6, 127.6, 127.5, 126.3, 122.2, 121.8,
77.1, 76.9, 65.0, 39.8, 39.7. IR (KBr, cmÀ1): 3446,
2971, 2880, 1652, 1513, 1208, 799. HRMS (ESIMS):
for C26H21NaO4 (M + Na)+ Anal. Calcd 421.1416; found
421.1441.
2-(3,4-Dimethoxyphenyl)-2,3-dihydroquinolin-4(1H)-one(1g).
1H-NMR (500MHz, CDCl3, ppm) δ 12.17 (s, 1H, D2O
exchangeable), 7.93 (d, J=10Hz, 1H), 7.51 (t,
J=10.5Hz, 1H), 7.01–7.08 (m, 4H), 6.91 (d, J=10Hz,
1H), 5.43 (dd, J=16.5, 2.5Hz, 1H), 3.93 (s, 3H), 3.91 (s,
3H), 3.13 (dd, J=21, 17Hz, 1H), 2.88 (dd, J=21, 2.5Hz,
1H). 13C-NMR (125MHz, CDCl3, ppm) δ 192.2, 161.6,
149.4, 149.3, 136.2, 131.2, 127.1, 120.9, 121.6, 118.8,
118.2, 111.1, 109.4, 79.6, 56.0, 55.9, 44.6. IR (KBr,
cmÀ1): 3110, 2837, 1687, 1598, 1026. GC–MS (m/z): 283
[M+, C17H17NO3].
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Das Gupta, A.; Mallik, A. K. Tetrahedron Lett 2011, 52, 5020; (e)
2-(2-Chlorophenyl)-2,3-dihydroquinolin-4(1H)-one (1c). 1H-
NMR (500MHz, CDCl3, ppm) δ 11.34 (s, 1H, D2O
exchangeable), 8.58 (d, J=6Hz, 1H), 7.87 (dd, J=10,
2.5Hz, 1H), 7.75–7.79 (m, 1H), 7.59 (d, J=10Hz, 1H),
7.44–7.48 (m, 1H), 7.26–7.29 (m, 1H), 6.98–7.03 (m, 2H),
5.60 (dd, J= 13.5, 6.5Hz, 1H), 3.06–3.16 (m, 2H). 13C-
NMR (125 MHz, CDCl3, ppm) δ 191.2, 160.8, 157.1, 148.4,
138.3, 136.2, 127.1, 123.8, 121.9, 121.4, 121.2, 118.1, 79.1,
42.8. IR (KBr, cmÀ1): 3164, 2926, 1693, 1606, 1462, 1305,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet