1750
S.-C. Yang, C.-W. Hung
PAPER
Table 4 (continued)
Prod- IR (CHCl3) 1H NMR (CDCl3/TMS)
13C NMR (CDCl3/TMS) MS
m/z
HRMS
m/z
ucta n (cm–1)
d, J (Hz)
d
3j
3440, 1600, (200 MHz): 3.87 (dt, J = 1.3, 5.1, 2 H, CH2), 5.04
990, 920 (br s, 1 H, NH), 5.20 (dq, J = 1.3, 10.2, 1 H,
(50.3 MHz): 45.70 (CH2), 178 (M+), 161, Calcd for C9H10N2O2
111.30 (CH), 117.12 151, 130, 117, 178.0742. Found
105, 91, 77 187.0743.
vinyl H), 5.28 (dq, J = 1.3, 17.2, 1 H, vinyl H), 5.90 (CH2), 126.36 (CH),
(ddt, J = 5.1, 10.2, 17.2, 1H, vinyl H), 6.55 (d, J = 133.41 (CH), 137.78 (C),
9.2, 2 H, ArH), 8.06 (d, J = 9.2, 2 H, ArH)
153.51 (C)
3k
3426, 1606, (200 MHz): 3.89 (dt, J = 1.6, 5.6, 2 H, CH2), 3.92
(50.3 MHz): 45.37 (CH2), 208 (M+), 193, Calcd for C10H12N2O3
1003, 928 (s, 3 H, CH3), 5.22 (dq, J = 1.6, 10.2, 1 H, vinyl H), 55.90 (CH3), 104.68 (CH), 181, 179, 165, 208.0848. Found
5.27 (br s, 1 H, NH), 5.28 (dq, J = 1.6, 17.2, 1 H,
106.97 (CH), 117.07
146, 118, 91
208.0846.
vinyl H), 5.92 (ddt, J = 5.2, 10.2, 17.2, 1 H, vinyl H), (CH2), 119.77 (CH),
6.48 (d, J = 8.9, 1 H, ArH), 7.61 (d, J = 2.4, 1 H,
ArH), 7.87 (dd, J = 2.4, 8.9, 1 H, ArH)
133.50 (CH), 137.18 (C),
144.04 (C), 145.20 (C)
3l
3410, 1620, (400 MHz): 3.72 (m, 2 H, CH2), 4.42 (br s, 1 H, NH), (100.6 MHz): 45.86
990, 910
249 (M++4),
Calcd for C9H9BrClN
244.9607. Found
5.15 (dq, J = 1.6, 10.4, 1 H, vinyl H), 5.22 (dq, J = (CH2), 107.58 (C), 112.42 247 (M++2),
1.6, 17.2, 1 H, vinyl H), 5.86 (ddt, J = 5.2, 10.4, 17.2, (CH), 116.52 (CH2),
245 (M+), 220, 244.9608.
1 H, vinyl H), 6.42 (d, J = 8.4, 1 H, ArH), 7.15 (dd, 119.54 (C), 130.43 (CH), 218, 212, 210,
J = 2.0, 8.8, 1 H, ArH), 7.32 (d, J = 2.0, 1 H, ArH) 131.14 (CH), 134.11
208, 206, 166,
164, 131
(CH), 142.81 (C)
3m18 1616, 1003, (200 MHz): 2.90 (s, 3 H, CH3), 3.88 (dt, J = 1.7, 5.1, (50.3 MHz): 37.93 (CH3), 147 (M+), 132, Calcd for C10H13N
933 2 H, CH2), 5.12 (dq, J = 1.7, 10.4, 1 H, vinyl H), 5.15 55.23 (CH2), 112.45 (CH), 120, 104, 91, 147.1048. Found
(dq, J = 1.7, 17.0, 1 H, vinyl H), 5.82 (ddt, J = 5.1, 116.08 (CH2), 116.41
10.4, 17.0, 1 H, vinyl H), 6.64–6.72 (m, 3 H, ArH), (CH), 129.08 (CH),
77
147.1048.
7.16–7.24 (m, 2 H, ArH)
133.82 (CH), 149.48 (C)
3n19 1606, 1003, (400 MHz): 1.14 (t, J = 7.2, 3 H, CH3), 3.35 (q, J = (100.6 MHz): 12.21
161 (M+), 146, Calcd for C11H15N
933 7.2, 2 H, CH2CH3), 3.86 (dt, J = 1.6, 4.8, 2 H, CH2), (CH3), 44.61 (CH2), 52.55 134, 118, 104, 161.1204. Found
5.11 (dq, J = 1.6, 10.0, 1 H, vinyl H), 5.15 (dq, J = (CH2), 112.04 (CH),
1.6, 17.2, 1 H, vinyl H), 5.84 (ddt, J = 4.8, 10.0, 17.2, 115.64 (CH2), 115.79
1 H, vinyl H), 6.62–6.69 (m, 3 H, ArH), 7.15–7.20 (CH), 129.06 (CH),
91, 77
161.1203.
(m, 2 H, ArH)
134.42 (CH), 148.11 (C)
4a20 1600, 980, (400 MHz): 3.91 (dt, J = 1.6, 4.8, 4 H, 2 × CH2), 5.14 (100.6 MHz): 52.71
173 (M+), 158, Calcd for C12H15N
146, 130, 118, 173.1204. Found
910 (dq, J = 1.6, 10.4, 2 H, vinyl H), 5.17 (dq, J = 1.6, (CH2), 112.33 (CH),
17.2, 2H, vinyl H), 5.85 (ddt, J = 5.2, 10.4, 17.2, 2 H, 115.94 (CH2), 116.28
vinyl H), 6.65–6.71 (m, 3 H, ArH), 7.17–7.21 (m, 2 (CH), 129.02 (CH),
104, 91, 77
173.1205.
H, ArH)
134.03 (CH), 148.68 (C)
4b
1610, 990, (400 MHz): 2.22 (s, 3 H, CH3), 3.86 (dt, J = 1.6, 4.8, (100.6 MHz): 20.15
187 (M+), 172, Calcd for C13H17N
160, 144, 130, 187.1359. Found
920
4 H, 2 × CH2), 5.12 (dq, J = 1.6, 10.0, 2 H, vinyl H), (CH3), 52.90 (CH2),
5.15 (dq, J = 1.6, 16.8, 2 H, vinyl H), 5.83 (ddt, J = 112.66 (CH), 115.84
4.8, 10.0, 16.8, 2 H, vinyl H), 6.46 (d, J = 8.8, 2 H, (CH2), 125.42 (C), 129.52
118, 91, 77
187.1360.
ArH), 6.99 (d, J = 8.8, 2H, ArH)
(CH), 134.27 (CH),
146.58 (C)
4c
1595, 990, (200 MHz): 3.89 (dt, J = 1.6, 4.8, 4 H, 2 × CH2), 5.14 (50.3 MHz): 52.94 (CH2), 209 (M++2),
920 (dq, J = 1.7, 9.7, 2 H, vinyl H), 5.15 (dq, J = 1.7, 17.6, 113.45 (CH), 116.16
2H, vinyl H), 5.83 (ddt, J = 4.8, 9.6, 17.6, 2 H, (CH2), 121.01 (C), 128.79 138, 130, 111, 207.0815.
vinyl H), 6.59 (d, J = 9.2, 2 H, ArH), 7.12 (d, J = 9.2, (CH), 133.51 (CH),
2 H, ArH) 147.37 (C)
Calcd for C12H14ClN
207 (M+), 180, 207.0817. Found
75
4d
1635, 995, (400 MHz): 3.74 (s, 3 H, OCH3), 3.85 (dt, J = 1.6, (100.6 MHz): 53.59
910 5.2, 4 H, 2 × CH2), 5.14 (dq, J = 1.6, 10.4, 2 H, (CH2), 55.75 (CH3),
vinyl H), 5.17 (dq, J = 1.6, 17.2, 2 H, vinyl H), 5.84 114.52 (CH), 114.63
203 (M+), 188, Calcd for C13H17NO
176, 162, 135, 203.1310. Found
120, 92, 77
203.1311.
(ddt, J = 5.2, 10.4, 17.2, 2 H, vinyl H), 6.68 (d,
J = 9.2, 2 H, ArH), 6.80 (d, J = 8.8, 2 H, ArH)
(CH), 116.08 (CH2),
134.55 (CH), 143.50 (C),
151.54 (C)
4e
1711, 1611, (200 MHz): 1.35 (t, J = 7.1, 3 H, CH3), 3.97 (dt, J = (50.3 MHz): 14.50 (CH3), 233 (M+), 218, Calcd for C15H19NO2
1038, 928 1.7, 4.6, 4 H, 2 × CH2), 4.31 (q, J = 7.1, 2 H, 52.65 (CH2), 60.09 (CH2), 204, 192, 190, 245.1416. Found
CH2CH3), 5.15 (dq, J = 1.7, 16.8, 2 H, vinyl H), 5.17 110.98 (CH), 116.42 177, 165, 137, 245.1414.
(dq, J = 1.6, 10.7, 2 H, vinyl H), 5.84 (ddt, J = 4.7, (CH2), 117.72 (C), 131.26 122, 107, 77
10.7, 16.8, 2 H, vinyl H), 6.64 (d, J = 9.2, 2 H, ArH), (CH), 132.81 (CH),
7.88 (d, J = 9.2, 2 H, ArH)
151.92 (C), 166.89 (C)
Synthesis 1999, No. 10, 1747–1752 ISSN 0039-7881 © Thieme Stuttgart · New York