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(400 MHz, CDCl3): d=7.22–7.18 (m, 4H), 7.14 (d, J=
8.4 Hz, 1H), 7.01 (s, 1H), 6.87 (d, J=8.4 Hz, 1H), 6.74 (t,
J=8.0 Hz, 1H), 3.90–3.80 (m, 8H), 2.39 (s, 3H); 13C NMR
(100 MHz, CDCl3): d=149.9, 149.2, 142.1, 136.4, 135.9,
130.5, 129.1, 127.1, 126.4, 125.8, 118.7, 116.7, 115.9, 111.2,
108.4, 56.0, 55.9, 36.0, 19.5; IR (KBr): n=3009, 2931, 2843,
2220, 1596, 1516, 1457, 1263, 1150, 1027, 854, 756 cmÀ1; HR-
MS-ESI: m/z=316.1310, calcd. for C19H19NNaO2 [M+Na]+:
316.1308.
(E)-2-(Thiophen-2-yl)-4-(o-tolyl)but-2-enenitrile
(3dq):
Purple oil; yield: 47.3 mg (66%); 1H NMR (400 MHz,
CDCl3): d=7.25 (d, J=3.6 Hz, 1H), 7.22 (d, J=5.2 Hz, 1H),
7.18 (s, 4H), 7.01 (t, J=4.0 Hz, 1H), 6.67 (t, J=8.0 Hz, 1H),
3.84 (d, J=8.0 Hz, 2H), 2.36 (s, 3H); 13C NMR (100 MHz,
CDCl3): d=142.0, 137.3, 136.4, 135.5, 130.6, 129.1, 127.8,
127.2, 126.7, 126.5, 125.9, 115.5, 110.8, 35.8, 19.5; IR (KBr):
n=3070, 3022, 2925, 2224, 1606, 1490, 1435, 1240, 838, 750,
705 cmÀ1
;
HR-MS-ESI:
m/z=262.0662,
calcd.
for
(Z)-2-(3,5-Dimethoxyphenyl)-4-(o-tolyl)but-2-enenitrile
C15H13NNaS [M+Na]+: 262.0661.
1
(3dl): Yellow oil; yield: 64.2 mg (73%); H NMR (400 MHz,
(Z)-2-(Benzo[b]thiophen-3-yl)-4-(o-tolyl)but-2-enenitrile
1
CDCl3): d=7.24–7.18 (m, 4H), 6.86 (t, J=8.0 Hz, 1H), 6.69
(d, J=2.0 Hz, 2H), 6.46 (t, J=2.0 Hz, 1H), 3.90 (d, J=
8.0 Hz, 2H), 3.81 (s, 6H), 2.39 (s, 3H); 13C NMR (100 MHz,
CDCl3): d=161.2, 144.6, 136.4, 135.7, 134.9, 130.6, 129.2,
127.2, 126.5, 116.5, 116.3, 104.0, 101.1, 55.5, 36.1, 19.5; IR
(KBr): n=3009, 2945, 2842, 2221, 1598, 1461, 1343, 1202,
(3dr): Yellow oil; yield: 37.3 mg (43%); H NMR (400 MHz,
CDCl3): d=7.97 (d, J=8.0 Hz, 1H), 7.85 (d, J=7.6 Hz, 1H),
7.54 (s, 1H), 7.44–7.36 (m, 2H), 7.25–7.18 (m, 4H), 6.86 (t,
J=8.0 Hz, 1H), 3.95 (d, J=8.0 Hz, 2H), 2.41 (s, 3H);
13C NMR (100 MHz, CDCl3): d=147.1, 140.5, 136.3, 136.0,
135.6, 130.6, 129.6, 129.1, 127.3, 126.6, 126.3, 125.0, 124.9,
123.1, 122.2, 116.6, 110.6, 36.0, 19.6; IR (KBr): n=3067,
3023, 2925, 2219, 1600, 1495, 1429, 832, 747 cmÀ1; HR-MS-
ESI: m/z=312.0819, calcd. for C19H15NNaS [M+Na]+:
312.0817.
(Z)-4-(2-Fluorophenyl)-2-(naphthalen-2-yl)but-2-eneni-
trile (3ao): Colorless needles; yield: 77.5 mg (90%); mp
123–1258C; 1H NMR (400 MHz, CDCl3): d=8.01 (s, 1H),
7.83 (d, J=7.2 Hz, 1H), 7.79 (d, J=8.4 Hz, 2H), 7.57 (d, J=
8.4 Hz, 1H), 7.49–7.47 (m, 2H), 7.30 (t, J=8.0 Hz, 1H),
7.25–7.22 (m, 1H), 7.13–7.05 (m, 2H), 7.01 (t, J=8.0 Hz,
1H), 3.96 (d, J=8.0 Hz, 2H); 13C NMR (100 MHz, CDCl3):
d=160.9 (d, J=244.7 Hz), 142.7, 133.2 (d, J=20.5 Hz),
130.7 (d, J=4.2 Hz), 130.0, 128.9 (d, J=8.0 Hz), 128.7, 128.4,
127.6, 126.9, 126.8, 126.0, 124.5 (d, J=3.6 Hz), 124.4 (d, J=
15.6 Hz), 122.2, 116.9, 116.4, 115.7, 115.5, 31.9 (d, J=
2.8 Hz); IR (KBr): n=3054, 2923, 2854, 2223, 1584, 1489,
1369, 1230, 817, 755 cmÀ1; HR-MS-ESI: m/z=310.1005,
calcd. for C20H14FNNa [M+Na]+: 310.1002.
1159, 1066, 1010, 840, 750 cmÀ1
; HR-MS-ESI: m/z=
316.1309, calcd. for C19H19NNaO2 [M+Na]+: 316.1308.
(Z)-4-(o-Tolyl)-2-(3,4,5-trimethoxyphenyl)but-2-enenitrile
(3dm): Yellow oil; yield: 81.4 mg (84%); 1H NMR
(400 MHz, CDCl3): d=7.24–7.19 (m, 4H), 6.78 (t, J=
7.6 Hz, 1H), 6.76 (s, 2H), 3.91 (s, 1H), 3.89 (s, 7H), 3.86 (s,
3H), 2.39 (s, 3H); 13C NMR (100 MHz, CDCl3): d=153.5,
143.5, 139.0, 136.4, 135.7, 130.6, 129.2, 128.4, 127.2, 126.4,
116.5, 116.2, 103.1, 60.8, 56.2, 36.1, 19.5; IR (KBr): n=2940,
2837, 2221, 1585, 1506, 1458, 1418, 1339, 1247, 1126, 832,
745 cmÀ1
C20H21NNaO3 [M+Na]+: 346.1414.
(Z)-2-(Benzo[d][1,3]dioxol-5-yl)-4-(o-tolyl)but-2-eneni-
;
HR-MS-ESI:
m/z=346.1415,
calcd.
for
trile (3dn): Colorless needles; yield: 60.7 mg (73%); mp
110–1128C; 1H NMR (400 MHz, CDCl3): d=7.20 (s, 4H),
7.07 (d, J=8.0 Hz, 1H), 6.99 (s, 1H), 6.81 (d, J=8.0 Hz,
1H), 6.71 (t, J=7.6 Hz, 1H), 5.99 (s, 2H), 3.88 (d, J=
8.0 Hz, 2H), 2.38 (s, 3H); 13C NMR (100 MHz, CDCl3): d=
148.4, 148.4, 142.4, 136.3, 135.9, 130.6, 129.1, 127.2, 127.2,
126.4, 120.3, 116.6, 115.8, 108.5, 105.6, 101.5, 36.0, 19.5; IR
(KBr): n=3073, 2219, 1577, 1495, 1442, 1228, 1039, 860,
Methyl (Z)-4-[3-cyano-3-(3-methoxyphenyl)allyl]benzoate
1
(3rj): Brown oil; yield: 69.1 mg (75%); H NMR (400 MHz,
CDCl3): d=8.01 (d, J=7.6 Hz, 2H), 7.35–7.25 (m, 3H), 7.14
(d, J=7.6 Hz, 1H), 7.06 (s, 1H), 6.92–6.88 (m, 2H), 3.96 (d,
J=8.0 Hz, 2H), 3.91 (s, 3H), 3.82 (s, 3H); 13C NMR
(100 MHz, CDCl3): d=166.7, 160.0, 143.3, 142.5, 134.0,
130.2, 130.0, 129.0, 128.6, 118.2, 117.0, 116.4, 114.8, 111.4,
55.3, 52.1, 38.1; IR (KBr): n=2921, 2853, 2220, 1714, 1588,
1448, 1270, 1029, 776, 692 cmÀ1; HRMS-ESI: m/z=330.1098,
calcd. for C19H17NNaO3 [M+Na]+: 330.1101.
(Z)-4-(3-Methoxyphenyl)-2-(p-tolyl)but-2-enenitrile (3lf):
Yellow oil; yield: 50.5 mg (64%); 1H NMR (400 MHz,
CDCl3): d=7.43 (d, J=7.6 Hz, 2H), 7.25 (t, J=8.0 Hz, 1H),
7.18 (d, J=7.6 Hz, 2H), 6.88–6.84 (m, 2H), 6.80 (d, J=
2.4 Hz, 2H), 3.86 (d, J=8.0 Hz, 2H), 3.80 (s, 3H), 2.35 (s,
3H); 13C NMR (100 MHz, CDCl3): d=160.0, 143.2, 139.2,
139.1, 130.1, 129.9, 129.6, 125.6, 120.9, 116.7, 116.2, 114.3,
112.3, 55.2, 38.2, 21.1; IR (KBr): n=3030, 2921, 2853, 2218,
1591, 1457, 1258, 1039, 798, 692 cmÀ1; HR-MS-ESI: m/z=
286.1204, calcd. for C18H17NNaO [M+Na]+: 286.1202.
737 cmÀ1
;
HR-MS-ESI:
m/z=300.0991,
calcd.
for
C18H15NNaO2 [M+Na]+: 300.0995.
(Z)-2-(Naphthalen-2-yl)-4-(o-tolyl)but-2-enenitrile (3do):
Colorless needles; yield: 64.5 mg (76%); mp 117–1188C;
1H NMR (400 MHz, CDCl3): d=8.02 (s, 1H), 7.84–7.82 (m,
1H), 7.79 (d, J=8.4 Hz, 2H), 7.57 (d, J=8.8 Hz, 1H), 7.51–
7.46 (m, 2H), 7.24–7.17 (m, 4H), 6.96 (t, J=7.6 Hz, 1H),
3.93 (d, J=8.0 Hz, 2H), 2.39 (s, 3H); 13C NMR (100 MHz,
CDCl3): d=144.1, 136.4, 135.8, 133.3, 133.1, 130.6, 130.1,
129.2, 128.8, 128.3, 127.6, 127.2, 126.9, 126.9, 126.5, 125.9,
122.2, 116.6, 116.4, 36.2, 19.6; IR (KBr): n=3067, 2221,
1722, 1545, 1232, 949 cmÀ1; HR-MS-ESI: m/z=306.1251,
calcd. for C21H17NNa [M+Na]+: 306.1253.
(Z)-2-(Naphthalen-1-yl)-4-(o-tolyl)but-2-enenitrile (3dp):
Yellow oil; yield: 47.5 mg (56%); 1H NMR (400 MHz,
CDCl3): d=8.12 (d, J=8.0 Hz, 1H), 7.91–7.89 (m, 2H),
7.61–7.53 (m, 2H), 7.48–7.43 (m, 2H), 7.31–7.29 (m, 1H),
7.23–7.21 (m, 3H), 6.73 (t, J=7.6 Hz, 1H), 4.03 (d, J=
8.0 Hz, 2H), 2.46 (s, 3H); 13C NMR (100 MHz, CDCl3): d=
150.3, 136.3, 135.6, 133.6, 132.0, 130.6, 129.8, 129.1, 128.6,
127.2, 127.2, 127.0, 126.6, 126.4, 125.3, 124.3, 117.2, 114.8,
36.1, 19.6; IR (KBr): n=3056, 2926, 2216, 1598, 1497, 1451,
(Z)-2-(4-Chlorophenyl)-4-phenylbut-2-enenitrile
(3gc):
Yellow oil; yield: 43.3 mg (57%); 1H NMR (400 MHz,
CDCl3): d=7.51 (d, J=8.0 Hz, 2H), 7.40–7.36 (m, 4H),
7.32–7.29 (m, 3H), 6.94 (t, J=8.0 Hz, 1H), 3.94 (d, J=
8.0 Hz, 2H); 13C NMR (100 MHz, CDCl3): d=145.0, 137.1,
135.2, 131.4, 129.2, 129.0, 128.6, 127.1, 127.0, 116.2, 115.2,
38.3; IR (KBr): n=3038, 2922, 2956, 2219, 1589, 1482, 1087,
941, 780 cmÀ1
; HR-MS-ESI: m/z=306.1257, calcd. for
C21H17NNa [M+Na]+: 306.1253.
Adv. Synth. Catal. 0000, 000, 0 – 0
9
ꢁ 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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