2016
N. K. KONDURU AND N. AHMED
7.86 (d, 2H, J ¼ 8.5 Hz), 8.16 (br, 1H, D2O-exchangeable, NH). 13C NMR (CDCl3,
125 MHz): d (ppm): 47.20, 76.17, 111.17, 116.56, 118.93, 119.54, 122.22, 123.10,
126.89, 127.20, 128.02, 129.23, 129.45, 130.05, 132.62, 136.05, 137.65, 140.53,
=
199.36. IR (KBr) v: 3420 (NH), 3376 (OH), 3058, 2923, 1679 (C O), 1589, 1400,
1262, 1093, 742, 704 cmꢂ1. HR-MS (m=z) for C23H18ClNNaO2 (M þ Naþ). Anal.
calcd. 398.1026; found 398.1000.
3-(4-Chlorophenyl)-2-hydroxy-3-(2-methyl-1H-indol-3-yl)-1-
(naphthalen-2-yl)propan-1-one (2r)
1
Yield: 74%; yellow semisolid; H NMR (CDCl3, 500 MHz): d (ppm): 2.17 (s,
3H), 3.72 (br, 1H, D2O-exchangeable, OH), 4.60 (d, 1H, J ¼ 7 Hz), 6.02 (d, 1H,
J ¼ 7 Hz), 6.89–6.95 (m, 3H), 7.12–7.19 (m, 3H), 7.33 (d, 1H, J ¼ 9.5 Hz), 7.51 (t,
1H, J ¼ 7 Hz), 7.67 (t, 1H, J ¼ 7.5 Hz), 7.79 (s, 1H), 7.96–8.03 (m, 5H), 8.21 (br,
1H, D2O-exchangeable, NH). 13C NMR (CDCl3, 125 MHz): d (ppm): 11.94,
47.18, 73.59, 99.95, 110.24, 111.23, 119.16, 119.55, 119.85, 120.72, 121.38, 123.23,
126.66, 127.51, 128.14, 128.79, 129.64, 130.44, 131.10, 131.89, 131.91, 132.13,
135.29, 135.53, 138.69, 202.17. IR (KBr) v: 3522 (OH), 3421 (NH), 3075, 2931,
1686 (C O), 1492, 1434, 1299, 1093, 1017 cmꢂ1. HR-MS (m=z) for C28H22ClNNaO2
=
(M þ Naþ). Anal. calcd. 462.1399; found. 462.1376.
3-(4-Chlorophenyl)-2-hydroxy-1-(naphthalen-2-yl)-3-(1H-pyrrol-
2-yl)propan-1-one (2t)
Yield: 70%; light yellow semisolid; 1H NMR (CDCl3, 500 MHz): d (ppm): 3.79
(br, 1H, D2O-exchangeable, OH), 4.79 (d, 1H, J ¼ 7.5 Hz), 5.87 (dd, 1H, J ¼ 7.5,
1.5 Hz), 6.02 (dd, 1H, J ¼ 5.5, 3.5 Hz), 6.13 (dd, 1H, J ¼ 5.5, 2.5 Hz), 6.4–6.54 (m,
1H), 6.71 (dd, 1H, J ¼ 3.5, 2.5 Hz), 6.77 (dd, 2H, J ¼ 6.5, 2 Hz), 6.95 (t, 1H, J ¼ 8 Hz),
7.01–7.04 (m, 2H), 7.05–7.11 (m, 1H), 7.16–7.18 (m, 1H), 7.30–7.38 (m, 2H), 7.51 (t,
1H, J ¼ 8 Hz), 8.19 (br, 1H, D2O-exchangeable, NH). 13C NMR (CDCl3, 125 MHz):
d (ppm): 47.12, 76.15, 100.89, 106.0, 108.4, 116.82, 118.0, 122.12, 123.12, 126.97,
127.90, 128.70, 129.31, 131.91, 132.1, 134.01, 136.08, 137.74, 165.31, 200.44. IR
=
(KBr) v: 3422 (NH), 3365 (OH) 3124, 2923, 1680 (C O), 1626, 1452, 1258, 1106,
744, 697 cmꢂ1. HR-MS (m=z) for C23H18ClNO2 calcd. 375.1026; found 375.1053.
Complete experimental details are available in the Supporting Information,
available online.
CONCLUSION
In conclusion, we have developed a mild and efficient procedure for regioselec-
tive ring opening of chalcone epoxide with nitrogen heterocycles using indium(III)
chloride as a catalyst to afford 1,3-diaryl-2-hydroxy-3-(1H-3-indolyl=2-pyrrolyl)
propan-1-ones.
ACKNOWLEDGMENT
N. K. K. thanks the Council of Scientific and Industrial Research, New Delhi,
for the award of a junior reaserch fellowship (NET).