122
A. Bourry, B. Rigo, G. Sanz and D. Couturier
Vol. 39
Table 1
Elemental Analysis of New Compounds (Calcd./Found)
Table 2
Yields and Physical Properties of New Compounds
-1
N°
19
20
21
22
23
24
25
26
27
28
29
30
Formula
C
H
N
O
N° Yield % MP °C (solvent)
IR (KBr, ν cm )
C
H
O
67.09
66.91
65.00
65.22
65.63
65.77
66.23
66.54
66.79
66.41
68.90
69.25
64.47
64.19
65.35
65.42
65.17
65.38
72.04
72.41
66.30
65.92
65.44
65.53
6.62
6.59
6.59
6.47
6.83
6.88
7.05
7.12
7.27
7.16
6.18
6.51
6.59
6.67
7.44
7.46
7.09
7.13
9.37
9.72
6.89
7.17
6.02
6.00
26.28
26.48
25.25
25.91
24.48
24.33
23.75
23.62
23.06
22.66
22.15
21.75
22.40
22.78
21.76
21.81
19.29
19.61
14.39
14.01
23.13
23.51
24.91
24.82
19
20
90
89
102-3 (AcOEt)
125-7 (AcOEt)
3490, 1590, 1510, 1435, 1130
1740, 1690, 1600, 1585, 1510,
1500, 1470, 1455, 1125
1730, 1690, 1595, 1510, 1465,
1450, 1130
17 20
5
C
C
C
C
C
H
NO
NO
NO
NO
NO
3.16
2.76
3.06
2.80
2.97
2.83
2.88
2.85
2.77
2.78
6.54
6.49
5.44
5.50
8.44
8.12
4.20
4.55
3.68
3.37
3.63
3.91
24 29
7
7
7
7
7
21
76
109 (AcOEt)
112 (AcOEt)
H
25 31
22
23
88
91
1750, 1690, 1595, 1510, 1470, 1130
H
147-8 (AcOEt/ether) 1730, 1680, 1590, 1580, 1500,
1450, 1120
26 33
H
24
25
26
20
95
92
70 (AcOEt)
1750, 1700, 1615, 1585, 1510, 1500,
1470, 1455, 1125
3640, 1670, 1655, 1625, 1590, 1505,
1465, 1455, 1120
3325, 1680, 1620, 1585, 1510, 1465,
1450, 1120
1670, 1615, 1585, 1515, 1470, 1125
3325, 1670, 1650, 1580, 1500,
1460, 1120
27 35
H
120 (AcOEt)
29 31
C
H N O
23 28 2 6
168-170 (AcOEt)
C
H N O •H O
27
28
95
33
164-166 (AcOEt)
90-92 (AcOEt)
28 36 2 6 2
C
C
H
N O
27 35
3
6
29
30
85
98
oil
1700, 1615, 1580, 1510, 1130
1775, 1705, 1610, 1595, 1515,
1470, 1140
H
N O
138-9 (AcOEt)
40 62
2
6
C
H NO •0.5H O
21 25 5 2
C
H NO
21 23 6
Table 3
NMR Spectra of New Compounds
N°
NMR (CDCl ) δ ppm
3
1
19
H: 2.89 (s, 1H), 3.73 (s, 3H), 3.76 (s, 6H), 3.77 (s, 3H), 5.62 (s, 1H), 6.54 (s, 2H), 6.82 (d, J = 8.7 Hz, 2H), 7.24 (d, J = 8.7 Hz, 2H).
C: 55.3, 56.1, 60.9, 75.9, 103.4, 114, 128, 136.1, 137.2, 139.9, 153.3, 159.2
13
1
20a
20b
H: 0.95 (t, J = 7 Hz, 3H), 1.80-2.16 (m, 1H), 2.20-2.54 (m, 2H), 2.54-2.82 (m, 1H), 3.52-3.70 (m, 2H), 3.78 (s, 6H), 3.75 (s, 3H), 3.76 (s, 3H),
4.12 (dd, J = 8.5, 1.1 Hz, 1H), 6.39 (s, 3H), 6.81 (d, J = 8.8 Hz, 2H), 6.98 (d, J = 8.8 Hz, 2H)
1
H: 1.04 (t, J = 7.2 Hz, 3H), 1.96-2.19 (m, 1H), 2.19-2.60 (m, 2H), 2.60-2.88 (m, 1H), 3.66-3.75 (m, 2H), 3.78 (s, 6H), 3.79 (s, 3H), 3.84 (s, 3H),
4.21 (d, J = 8.4 Hz, 1H), 6.35 (s, 2H), 6.43 (s, 1H), 6.82 (d, J = 8.8 Hz, 2H), 7.15 (d, J = 8.8 Hz, 2H)
13
C: 13.8, 24.8, 29.8, 55.3, 56.2, 58.7, 58.9, 60.9, 61.2, 104.6, 113.7, 129.9, 131.7, 135.1, 136.9, 153.5, 159.5, 172.2, 175.6
1
21a
21b
22a
22b
23a
23b
H: 0.97 (d, J = 5.6 Hz, 3H), 1.0 (d, J = 5.6 Hz, 3H), 1.95-2.10 (m, 1H), 2.30-2.60 (m, 2H), 2.60-2.80 (m, 1H), 3.78 (s, 9H), 3.82 (s, 3H), 4.16 (t,
J = 8.3 Hz, 1H), 4.59 (m, 1H), 6.47 (s, 3H), 6.87 (d, J = 8.9 Hz, 2H), 7.04 (d, J = 8.9 Hz, 2H)
H: 0.97 (d, J = 6.2 Hz, 3H), 1.04 (d, J = 6.2 Hz, 3H), 1.90-2.10 (m, 1H), 2.20-2.60 (m, 2H), 2.60-2.90 (m, 1H), 3.79 (s, 9H), 3.84 (s, 3H), 4.18
1
(t, J = 8.4 Hz, 1H), 4.57 (m, 1H), 6.34 (s, 2H), 6.42 (s, 1H), 6.81 (d, J = 8.8 Hz, 2H), 7.16 (d, J = 8.8 Hz, 2H)
1
H: 0.87 (t, J = 7.2 Hz, 3H), 1.1-1.5 (m, 4H), 1.9-2.1 (m, 1H), 2.2-2.6 (m, 2H), 2.6-2.8 (m, 1H), 3.5-3.7 (m, 2H), 3.78 (s, 6H), 3.82 (s, 3H), 3.83
(s, 3H), 4.22 (d, J = 8.4 Hz, 1H), 6.46 (s, 3H), 6.87 (d, J = 8.7 Hz, 2H), 7.05 (d, J = 8.7 Hz, 2H)
1
H: 0.88 (t, J = 7 Hz, 3H), 1.1-1.5 (m, 4H), 1.9-2.2 (m, 1H), 2.2-2.6 (m, 2H), 2.6-2.8 (m, 1H), 3.5-3.7 (m, 2H), 3.78 (s, 9H), 3.84 (s, 3H), 4.22 (d,
J = 8.4 Hz, 1H), 6.34 (s, 2H), 6.43 (s, 1H), 6.81 (d, J = 8.8 Hz, 2H), 7.15 (d, J = 8.8 Hz, 2H)
1
H: 0.86 (t, J = 6.7 Hz, 3H), 1.12-1.29 (m, 4H), 1.29-1.48 (m, 2H), 1.95-2.10 (m, 1H), 2.22-2.57 (m, 2H), 2.60-2.85 (m, 1H), 3.54-3.75 (m, 2H),
3.78 (s, 6H), 3.82 (s, 3H), 3.83 (s, 3H), 4.18 (dd, J = 8.1, 1.2 Hz, 1H), 6.46 (s, 3H), 6.87 (d, J = 8.8 Hz, 2H), 7.05 (d, J = 8.8 Hz, 2H)
1
H: 0.88 (t, J = 6.7 Hz, 3H), 1.12-1.29 (m, 4H), 1.29-1.47 (m, 2H), 1.99-2.11 (m, 1H), 2.24-2.54 (m, 2H), 2.63-2.83 (m, 1H), 3.52-3.73 (m, 2H),
3.78 (s, 6H), 3.79 (s, 3H), 3.84 (s, 3H), 4.22 (dd, J = 8.4, 1.0 Hz, 1H), 6.34 (s, 2H), 6.43 (s, 1H), 6.81 (d, J = 9.4 Hz, 2H), 7.15 (d, J = 9.4 Hz,
2H)
13
C: 13.9, 22.3, 24.9, 28.0, 29.7, 29.9, 55.3, 56.2, 58.7, 58.9, 60.9, 65.5, 104.6, 113.7, 129.9, 131.7, 135.1, 137.4, 153.5, 159.5, 172.3, 175.6
1
24a
24b
H: 1.95-2.22 (m, 1H), 2.22-2.57 (m, 2H), 2.6-2.85 (m, 1H), 3.73 (s, 6H), 3.83 (s, 6H), 4.27 (d, J = 8.5 Hz, 1H), 4.62 (d, J = 12.1 Hz, 1H), 4.72
(d, J = 12.1 Hz, 1H), 6.48 (s, 3H), 6.85 (d, J = 8.7 Hz, 2H), 7.04 (d, J = 8.7 Hz, 2H), 7.1-7.2 (m, 2H), 7.25-7.35 (m, 3H)
H: 1.95-2.22 (m, 1H), 2.22-2.57 (m, 2H), 2.6-2.85 (m, 1H), 3.74 (s, 6H), 3.75 (s, 3H), 3.78 (s, 3H), 4.23 (d, J = 8.4 Hz, 1H), 4.66 (s, 2H), 6.36
1
(s, 2H), 6.45 (s, 1H), 6.80 (d, J = 8.6 Hz, 2H), 7.15 (d, J = 8.6 Hz, 2H), 7.08-7.2 (m, 2H), 7.25-7.35 (m, 3H)
13
24a,b C: 24.58, 24.63, 29.76, 29.82, 55.27, 55.30, 56.06, 58.38, 58.51, 58.98, 59.04, 60.79, 60.86, 104.63, 107.15, 113.74, 114.05, 128.07, 128.27,
128.54, 128.62, 128.71, 128.74, 129.84, 130.35, 131.58, 133.88, 134.94, 137.34, 137.49, 153.14, 153.44, 159.09, 159.47, 172, 172.14, 175.60,
175.71
1
25a
25b
H: 2-2.26 (m, 1H), 2.26-2.58 (m, 2H), 2.40 (d, J = 4.9 Hz, 3H), 2.58-2.83 (m, 1H), 3.81 (s, 6H), 3.82 (s, 3H), 3.84 (s, 3H), 4.03 (dd, J = 8.4, 1.4
Hz, 1H), 4.96 (bq, J = 4.9 Hz, 1H), 6.47 (s, 1H), 6.51 (s, 2H), 6.88 (dt, J = 8.7, 2.4 Hz, 2H), 7.01 (dt, J = 8.7, 2.4 Hz, 2H)
H: 2.07-2.25 (m, 1H), 2.27-2.58 (m, 2H), 2.34 (d, J = 4.9 Hz, 3H), 2.58-2.82 (m, 1H), 3.77 (s, 6H), 3.81 (s, 3H), 3.84 (s, 3H), 4.10 (dd, J = 8.5,
1
1.5 Hz, 1H), 4.90 (bq, J = 4.9 Hz, 1H), 6.29 (s, 2H), 6.46 (s, 1H), 6.87 (dt, J = 8.8, 2.6 Hz, 2H), 7.21 (dt, J = 8.8, 2.6 Hz, 2H)