1
1
+
55.7, 148.8, 145.4, 135.8, 134.0, 129.9, 129.8, 128.7, 128.4,
1-(4-Dim eth ylam in oph en yl)-3-(2-h ydr oxyph en yl)pr opan -
1-on e (6m ): 1H NMR δ 8.90 (bs, 1H), 7.89 (d, 2H, J ) 9.1 Hz),
7.10 (m, 2H), 6.88 (m, 2H), 6.62 (d, 2H, J ) 9.1 Hz), 3.37 (t, 2H,
28.36, 114.2, 103.0, 102.5, 38.5, 21.7, 16.7; MS m/e 413 (5) [M
+
+
H] 430(100) [M + NH
4
] ; HRMS calcd for C22
20 6
H O S 412.0981
1
3
,
found 412.0980.
J ) 5.7 Hz), 3.06 (s, 6H), 3.02 (t, 2H, J ) 5.7 Hz); C NMR δ
199.7, 154.9, 153.8, 130.7, 130.5, 128.4, 127.8, 123.8, 120.3, 117.7,
110.5, 39.9, 39.6, 23.5; IR (CsI) 3198, 2902, 1595, 1545, 1487,
3
-(2-Hyd r oxyp h en yl)-1-(3,4-d im eth oxyp h en yl)p r op a n -1-
1
on e (6h ): H NMR δ 8.20 (bs, 1H), 7.61 (dd, 1H, J ) 8.6, 2.2
+
Hz), 7.54 (d, 1H, J ) 2.2 Hz), 7.13 (d, 1H, J ) 7.2 Hz), 7.11 (t,
1378, 1254, 1183; MS m/e 252 (20), 270 (100) [M + H] ; HRMS
1
H, J ) 7.2 Hz), 6.90 (d, 1H, J ) 7.2 Hz), 6.87 (d, 1H, J ) 8.6
2
calcd for C17H19NO 269.1416, found 269.1413.
Hz), 6.85 (t, 1H, J ) 7.2 Hz), 3.94 (s, 3H), 3.92 (s, 3H), 3.42 (t,
1-(5-Ch lor oth iop h en -2-yl)-3-(2-h yd r oxyp h en yl)p r op a n -
1-on e (6n ): 1H NMR δ 7.53 (d, 1H, J ) 4.0 Hz), 7.12 (t, 1H, J
) 7.2 Hz), 7.11 (d, 1H, J ) 7.2 Hz), 6.95 (d, 1H, J ) 4.0 Hz),
6.87 (m, 2H), 3.30 (t, 2H, J ) 6.2 Hz), 3.01 (t, 2H, J ) 6.2 Hz);
1
3
2
1
1
1
H, J ) 6.1 Hz), 3.03 (t, 2H, J ) 6.1 Hz); C NMR δ 200.4,
54.5, 153.7, 148.9, 130.5, 129.2, 127.9, 123.2, 120.5, 117.3, 110.2,
09.9, 56.0, 55.9, 39.8, 23.6; IR (CsI) 3320, 2936, 1656, 1594,
-1
13
586, 1516, 1456, 1419, 1270, 1153, 1022 cm ; MS m/e 287 (100)
C NMR δ 193.5, 154.3, 141.6, 140.5, 132.3 (CH), 130.5 (CH),
+
]+; HRMS calcd for C17
[
2
M + H] , 304 (3) [M + NH
4
H
18
O
4
128.1 (CH), 127.7 (CH), 127.3, 120.8 (CH), 117.3 (CH), 39.9
(CH ), 23.6 (CH ); IR (CsI) 3376, 3098, 2932, 1646, 1456, 1418,
86.1205, found 286.1190
-(2-Hyd r oxyp h en yl)-1-(3,4-m eth ylen ed ioxyp h en yl)p r o-
2
2
-
1
+
3
1325, 1238, 1214, 1011 cm ; MS m/e 267 (100) [M + H] , 269
(35); HRMS calcd for C13H11ClO S 266.0168, found 266.0167.
1
p a n -1-on e (6i): H NMR δ 8.10 (bs, 1H), 7.61 (dd, 1H, J ) 8.2,
2
1
6
3
1
.9 Hz), 7.44 (d, 1H, J ) 1.9 Hz), 7.10 (m, 2H), 6.92 (m, 2H),
.87 (d, 1H, J ) 8.2 Hz), 6.03 (s, 2H), 3.36 (t, 2H, J ) 6.0 Hz),
.01 (t, 2H, J ) 6.0 Hz); 13C NMR δ 199.9, 154.4, 152.2, 148.1,
30.5, 127.8, 124.8, 120.5, 117.2, 107.9, 107.8, 101.9, 40.0, 23.6;
1
-(4-Cya n op h en yl)-3-(2-h yd r oxyp h en yl)p r op a n -1-on e
1
(
6o): H NMR δ 8.04 (d, 2H, J ) 8.8 Hz), 7.74 (d, 2H, J ) 8.8
Hz), 7,13 (m, 2H), 6.88 (m, 2H), 3.41 (t, 2H, J ) 6.6 Hz), 3.05 (t,
H, J ) 6.6 Hz); C NMR δ 200.1, 154.0, 139.1, 132.4, 130.5,
28.5, 127.9, 127.0, 121.8, 120.7, 117.7, 116.5, 40.0, 23.9; IR (CsI)
421, 3067, 2933, 2232, 1686, 1608, 1594, 1504, 1490, 1456,
405, 1364, 1294, 1233, 1205, 1099, 982, 843, 758 cm ; MS m/e
52 (21) [M + H] , 274 (100); HRMS calcd for C16
51.0946, found 251.0944.
13
2
1
3
1
2
2
IR (CsI) 3332, 3077, 2903, 1662, 1603, 1489, 1444, 1358, 1295,
1
HRMS calcd for C16
254, 1112, 1039 cm-1; MS m/e 271 (12) [M + H] , 293 (100)
270.0892, found 270.0881.
-(3,4-Bis-ben zyloxyph en yl)-3-(2-h ydr oxyph en yl)pr opan -
+
;
H
14
O
4
-1
1
+
H
13NO
2
1
1
-on e (6j): H NMR δ 8.14 (bs, 1H), 7.62 (s,1H), 7.57 (dd, 1H, J
)
1
2
8.4, 1.9 Hz), 7.39 (m, 11H), 7.10 (d, 1H, J ) 7.5 Hz), 6.92 (d,
3
-(2,4-Dih yd r oxyp h en yl)-1-(3,4,5-tr im eth oxyp h en yl)p r o-
H, J ) 8.4 Hz), 6.85 (t, 1H, J ) 7.5 Hz), 5.23 (s, 2H), 5.18 (s,
1
p a n -1-on e (6p ): H NMR δ 7.22 (s, 2H), 6.92 (d, 1H, J ) 8.1
H), 3.35 (t, 2H, J ) 5.8 Hz), 3.00 (t, 2H, J ) 5.8 Hz); 13C NMR
Hz), 6.43 (d, 1H, J ) 3.7 Hz), 6.35 (dd, 1H, J ) 8.1 Hz, J ) 3.7
δ 200.4, 154.6, 153.7, 148.6, 136.6, 136.3, 130.5, 129.5, 128.6,
Hz), 3.90 (s, 3H), 3.87 (s, 6H), 3.33 (t, 2H, J ) 6.2 Hz), 2.93 (t,
1
1
1
4
28.55, 128.1, 128.0, 127.4, 127.0, 123.5, 120.6, 117.6, 113.8,
12.8, 71.1, 70.8, 40.0, 23.4; IR (CsI) 3320, 3064, 3035, 2935,
13
2
1
2
H, J ) 6.2 Hz); C NMR δ 201.2, 155.7, 155.2, 152.9, 131.3,
19.7, 107.9, 105.9, 104.2, 60.9, 56.2, 40.2, 23.4; IR (CsI) 3411,
-
1
658, 1591, 1512, 1456, 1428, 1269, 1147, 1020 cm ; MS m/e
-1
920, 1660, 1619, 1588, 1507, 1459, 1416, 1331, 1155, 1127 cm
;
+
]+; HRMS calcd for
39 (11) [M + H] , 456 (100) [M + NH
4
+
(M•+)
MS m/e 333 (100) [M + H] ; HRMS calcd for C18
32.1260, found 332.1260.
-(2,4-Dih yd r oxy-6-tosyloxyp h en yl)-1-(3,4,5-tr im eth oxy-
H
20
O
6
C
29
H
26
O
4
438.1831, found 438.1828.
3
3
-(2-Hydr oxyph en yl)-1-n aph th alen -2-ylpr opan -1-on e (6k):
3
1
H NMR δ 8.52 (s, 1H), 7.86 (m, 5H), 7.56 (m, 2H), 7.16 (d, 1H,
1
p h en yl)p r op a n -1-on e (6q): H NMR δ 8.80 (bs, 1H), 7.80 (d,
J ) 7.6 Hz), 7.13 (t, 1H, J ) 7.6 Hz), 6.94 (d, 1H, J ) 7.6 Hz),
6
2
1
2
1
1
H, J ) 7.9 Hz), 7.34 (d, 2H, J ) 7.9 Hz), 7.24 (s, 2H), 6.35 (s,
H), 6.09 (s, 1H), 3.90 (s, 9H), 3.40 (t, 2H, J ) 5.5 Hz), 2.84 (t,
.89 (t, 1H, J ) 7.6 Hz), 3.61 (t, 2H, J ) 5.9 Hz), 3.11 (t, 2H, J
1
3
)
5.9 Hz); C NMR δ 201.9, 154.5, 135.8, 133.4, 132.3, 130.6,
13
H, J ) 5.5 Hz), 2.43 (s, 3H); C NMR δ 202.1, 156.7, 155.5,
1
4
1
30.3, 129.6, 128.8, 128.5, 128.0, 127.8, 126.9, 123.7, 120.7, 117.4,
0.4, 23.6; IR(CsI) 3331, 3058, 2930, 1665, 1626, 1594, 1456,
53.0, 149.6, 145.7, 143.3, 133.1, 131.0, 130.0, 128.2, 113.7, 106.0,
03.6, 101.6, 60.9, 56.3, 38.6, 21.6, 17.1; MS m/e 503 (100) [M +
-
1
+
372, 1276, 1239, 1184 cm ; MS m/e 277 (31) [M + H] , 299
276.1150, found 276.1145.
-(2-Hyd r oxyp h en yl)-1-(3,4,5-tr im eth oxyp h en yl)p r op a n -
+
•+
H] ; HRMS calcd for C25
26 9
H O S (M ) 502.1298, found 502.1297.
16 2
(100); HRMS calcd for C19H O
3
1
Ack n ow led gm en t. The mass spectra data were
recorded by A.Valleix (CEA Saclay). The project was
supported by a grant from the MENRT (A.B.).
1
6
3
2
1
-on e (6l): H NMR δ 7.88 (bs, 1H), 7.25 (s, 2H), 7.11 (m, 2H),
.91 (d, 1H, J ) 7.3 Hz), 6.86 (t, 1H, J ) 7.3 Hz), 3.90 (bs, 9H),
.41 (t, 2H, J ) 5.5 Hz), 3.04 (t, 2H, J ) 5.5 Hz); 13C NMR δ
00.6, 154.4, 153.0, 143.2, 131.3, 130.6 (CH), 128.0 (CH), 127.7,
20.7 (CH), 117.3 (CH), 105.9 (CH), 61.0 (CH
3 3
), 56.3 (CH ), 40.2
Su p p or tin g In for m a tion Ava ila ble: General experimen-
tal methods and H/ C NMR spectra. This material is avail-
able free of charge via the Internet at http://pubs.acs.org.
(CH
2
), 23.7 (CH ); IR(CsI) 3421, 2940, 2838, 1663, 1586, 1506,
2
1
13
-
1
+
1
3
3
457, 1414, 1330, 1235, 1127 cm ; MS m/e 317 (63) [M + H] ,
+
4 20 5 ,
34 (100) [M + NH ] ; HRMS calcd for C18H O 316.1311 found
16.1307.
J O034936C
J . Org. Chem, Vol. 69, No. 4, 2004 1377