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RSC Advances
(cm21) 3060, 2922, 2198, 1663, 1598, 1484, 1295, 1274, 1119,
1038, 950, 785, 760, 714, 617, 603; HRMS (ES) Calcd for
C21H16ONa 307.1099 [M + Na]+, found 307.1105.
9.96 (s, 1H), 7.98 (d, J = 8.1 Hz, 1H), 7.90–7.83 (m, 2H), 7.76 (d,
J = 8.2 Hz, 2H), 7.57–7.47 (m, 4H), 7.36 (d, J = 8.1 Hz, 2H), 4.37
(s, 2H); 13C NMR (CDCl3, 100 MHz) d 191.2, 185.0, 137.0, 133.9,
133.4, 132.4, 129.5, 129.4, 128.93, 128.91, 128.7, 126.7, 126.1,
125.7, 125.5, 123.9, 90.8, 89.7, 49.9; IR (neat) n (cm21) 3060,
2924, 2840, 2735, 2205, 1702, 1668, 1602, 1564, 1511, 1389,
1327, 1303, 1280, 1204, 1167, 1102, 1083, 953, 911, 830, 792,
780, 699; HRMS (EI) Calcd for C21H14O2 298.0994 [M]+, found
298.1003.
1-(Naphthalen-1-yl)-4-(m-tolyl)but-3-yn-2-one (4c). Yellow oil
(119.4 mg, 84% yield). 1H NMR (CDCl3, 400 MHz) d 7.98 (d, J =
8.3 Hz, 1H), 7.85 (d, J = 4.0 Hz, 1H), 7.81 (dd, J = 8.5, 3.9 Hz,
1H), 7.55–7.41 (m, 4H), 7.17–6.97 (m, 4H), 4.32 (s, 2H), 2.22 (s,
3H); 13C NMR (CDCl3, 100 MHz) d 185.4, 138.4, 134.0, 133.7,
132.5, 131.8, 130.3, 130.1, 128.9, 128.5, 126.6, 126.0, 125.6,
124.1, 119.5, 93.7, 87.6, 49.9, 21.1; IR (neat) n (cm21) 3047,
2921, 2188, 1718, 1664, 1597, 1511, 1483, 1456, 1398, 1297,
1208, 1098, 1017, 884, 786, 775, 732, 688; HRMS (ES) Calcd for
C21H16ONa 307.1099 [M + Na]+, found 307.1095.
1-(Naphthalen-1-yl)-4-(p-tolyl)but-3-yn-2-one (4d). Yellow oil
(123.6 mg, 87% yield). 1H NMR (CDCl3, 400 MHz) d 7.97 (d, J =
8.2 Hz, 1H), 7.87–7.71 (m, 2H), 7.53–7.37 (m, 4H), 7.12 (d, J =
8.0 Hz, 2H), 7.00 (d, J = 8.0 Hz, 2H), 4.29 (s, 2H), 2.24 (s, 3H);
13C NMR (CDCl3, 100 MHz) d 185.4, 141.7, 134.0, 133.2, 132.5,
130.2, 129.4, 128.9, 128.5, 126.6, 126.0, 125.7, 124.1, 116.7,
94.0, 88.1, 50.0, 21.8; IR (neat) n (cm21) 3046, 2920, 2198, 2147,
1759, 1662, 1605, 1509, 1445, 1398, 1289, 1217, 1083, 951, 875,
817, 784, 732, 707; HRMS (ES) Calcd for C21H16ONa 307.1099
[M + Na]+, found 307.1490.
4-(4-Methoxyphenyl)-1-(naphthalen-1-yl)but-3-yn-2-one (4e).
Yellow solid (139.6 mg, 93% yield), mp: 84–86 uC. 1H NMR
(CDCl3, 400 MHz) 8.08 (d, J = 8.1 Hz, 1H), 7.96–7.85 (m, 2H),
7.61–7.50 (m, 4H), 7.25 (d, J = 8.5 Hz, 2H), 6.81 (d, J = 8.5 Hz,
2H), 4.39 (s, 2H), 3.76 (s, 3H); 13C NMR (CDCl3, 100 MHz) d
185.4, 161.8, 135.2, 134.0, 132.5, 130.3, 128.8, 128.4, 126.6,
126.0, 125.6, 124.2, 114.3, 111.4, 94.6, 87.9, 55.4, 49.8; IR (KBr)
n (cm21) 3312, 3043, 2900, 2553, 2184, 1665, 1601, 1509, 1326,
1296, 1253, 1184, 1109, 1066, 1027, 916, 835, 808, 784, 775,
731; HRMS (ES) Calcd for C21H16O2Na 323.1048 [M + Na]+,
found 323.1054.
1-(Naphthalen-1-yl)-4-(4-nitrophenyl)but-3-yn-2-one (4i).
1
Yellow solid (104.6 mg, 82% yield), mp: 149–151 uC. H NMR
(CDCl3, 400 MHz) d 8.12 (ddd, J = 8.0, 4.0, 4.0 Hz, 2H), 7.97 (d, J
= 8.2 Hz, 1H), 7.92–7.83 (m, 2H), 7.58–7.46 (m, 4H), 7.34 (ddd, J
= 8.0, 4.0, 4.0 Hz, 2H), 4.37 (s, 2H); 13C NMR (CDCl3, 100 MHz)
d 184.7, 148.4, 134.0, 133.6, 132.4, 129.4, 128.9, 128.7, 126.7,
126.3, 126.1, 125.6, 123.84, 123.76, 123.6, 90.4, 89.2, 49.8; IR
(KBr) n (cm21) 3104, 3062, 2949, 2914, 2210, 1668, 1596, 1521,
1345, 1287, 1187, 1107, 1013, 916, 859, 839, 781, 749, 712, 686;
HRMS (ES) Calcd for C20H13NO3Na 338.0793 [M + Na]+, found
338.0786.
1,4-Diphenylbut-3-yn-2-one (6a)7b. Yellow solid (93.6 mg,
1
85% yield), H NMR (CDCl3, 400 MHz) d 7.47–7.20 (m, 10H),
3.93 (s, 2H); 13C NMR (CDCl3, 400 MHz) d 185.2, 133.3, 133.1,
130.8, 129.9, 128.7, 128.6, 127.4, 119.9, 92.9, 87.7, 52.2.
4-Phenyl-1-(p-tolyl)but-3-yn-2-one (6b)7b. Yellow oil (96.1 mg,
82% yield), 1H NMR (CDCl3, 400 MHz) d 7.47–7.37 (m, 3H),
7.35–7.28 (m, 2H), 7.21–7.13 (m, 4H), 3.87 (s, 2H), 2.33 (s, 3H);
13C NMR (CDCl3, 100 MHz) d 185.4, 137.1, 133.1, 130.8, 130.2,
129.8, 129.5, 128.7, 119.9, 92.7, 87.9, 51.9, 21.2.
1-(4-Methoxyphenyl)-4-phenylbut-3-yn-2-one (6c)14
. Brown
oil (95.1 mg, 76% yield). 1H NMR (CDCl3, 400 MHz) d 7.47–
7.31 (m, 5H), 7.22 (d, J = 8.5 Hz, 2H), 6.89 (d, J = 8.5 Hz, 2H),
3.85 (s, 2H), 3.78 (s, 3H); 13C NMR (CDCl3, 100 MHz) d 185.6,
159.0, 133.1, 130.9, 130.8, 128.6, 125.2, 119.9, 114.2, 92.7, 87.8,
55.3, 51.3.
4-(4-Fluorophenyl)-1-(naphthalen-1-yl)but-3-yn-2-one (4f).
Yellow solid (132.6 mg, 92% yield), mp: 91–93 uC. 1H NMR
(CDCl3, 400 MHz) d 7.96 (d, J = 8.3 Hz, 1H), 7.85–7.75 (m, 2H),
1-(4-Fluorophenyl)-4-phenylbut-3-yn-2-one (6d)7b
.
Yellow
solid (103.6 mg, 87% yield), 1H NMR (CDCl3, 400 MHz) d
7.47–7.40 (m, 3H), 7.36–7.24 (m, 4H), 7.05 (dd, J = 8.8, 8.8 Hz,
2H), 3.89 (s, 2H); 13C NMR (CDCl3, 100 MHz) d 184.9, 162.3 (d,
1JC–F = 244.4 Hz), 133.1, 131.5, 131.4, 131.0, 128.7, 119.7, 115.6
7.51–7.35 (m, 4H), 7.17–7.11 (m, 2H), 6.93–6.80 (m, 2H), 4.28
1
(s, 2H); 13C NMR (CDCl3, 100 MHz) d 185.3, 164.0 (d, JC–F
=
252.4 Hz), 135.5, 135.4, 134.0, 132.5, 130.0, 128.9, 128.6, 126.7,
2
3
2
126.0, 125.7, 124.1, 116.1 (d, JC–F = 22.2 Hz), 115.8 (d, JC–F
=
(d, JC–F = 21.3 Hz), 93.1, 87.6, 76.8, 51.2.
3.5 Hz), 92.2, 87.7, 49.9; IR (KBr) n (cm21) 3064, 2204, 1760,
1666, 1598, 1505, 1398, 1352, 1328, 1291, 1233, 1186, 1098,
1039, 1015, 951, 910, 838, 792, 778, 732, 711, 690; HRMS (EI)
Calcd for C20H13FO 288.0950 [M]+, found 288.0958.
1-(2-Methoxyphenyl)-4-phenylbut-3-yn-2-one (6e). Yellow oil
1
(75.1 mg, 60% yield). H NMR (CDCl3, 400 MHz) d 7.49–7.40
(m, 3H), 7.37–7.25 (m, 3H), 6.91 (d, J = 7.7 Hz, 1H), 6.87–6.83
(m, 2H), 3.90 (s, 2H), 3.80 (s, 3H); 13C NMR (CDCl3, 100 MHz) d
185.0, 159.9, 134.6, 133.1, 130.8, 129.7, 128.6, 122.3, 119.9,
115.5, 113.0, 92.9, 87.7, 55.2, 52.2; IR (neat) n (cm21) 3356,
2934, 2837, 2203, 1666, 1598, 1585, 1489, 1454, 1256, 1107,
1047, 930, 759, 689, 616; HRMS (EI) Calcd for C17H14O2
250.0994 [M]+, found 250.0991.
1-(2-Bromophenyl)-4-phenylbut-3-yn-2-one (6f). Yellow solid
(97.2 mg, 65% yield), mp: 48–50 uC. 1H NMR (CDCl3, 400 MHz)
d 7.62 (d, J = 7.9 Hz, 1H), 7.45–7.41 (m, 3H), 7.38–7.30 (m, 4H),
7.22–7.15 (m, 1H), 4.10 (s, 2H); 13C NMR (CDCl3, 100 MHz) d
184.0, 133.9, 133.4, 133.1, 132.2, 131.0, 129.4, 128.7, 127.8,
125.6, 119.9, 93.0, 87.8, 52.2; IR (KBr) n (cm21) 3059, 2203,
1668, 1595, 1570, 1489, 1442, 1279, 1129, 1077, 1026, 999, 757,
4-(4-Bromophenyl)-1-(naphthalen-1-yl)but-3-yn-2-one (4g).
1
Yellow solid (153.5 mg, 88% yield), mp: 148–150 uC. H NMR
(CDCl3, 400 MHz) d 7.96 (d, J = 8.5 Hz, 1H), 7.88–7.79 (m, 2H),
7.54–7.44 (m, 4H), 7.36 (d, J = 8.4 Hz, 2H), 7.03 (d, J = 8.4 Hz,
2H), 4.32 (s, 2H); 13C NMR (CDCl3, 100 MHz) d 185.2, 134.4,
133.9, 132.4, 131.9, 129.8, 128.9, 128.6, 126.6, 126.0, 125.7,
125.6, 124.0, 118.6, 91.8, 88.5, 49.8; IR (KBr) n (cm21) 3315,
3061, 2904, 2204, 1762, 1665, 1597, 1584, 1485, 1395, 1279,
1236, 1217, 1186, 1110, 1085, 1011, 951, 825, 781, 650, 608,
557, 530, 510; HRMS (ES) Calcd for C20H13BrONa 371.0047 and
373.0027 [M + Na]+, found 371.0038 and 373.0017.
4-(4-(Naphthalen-1-yl)-3-oxobut-1-yn-1-yl)benzaldehyde (4h).
1
Yellow oil (92.4 mg, 62% yield). H NMR (CDCl3, 400 MHz) d
18990 | RSC Adv., 2013, 3, 18985–18991
This journal is ß The Royal Society of Chemistry 2013