Takahiko Akiyama et al.
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2H, J 7.3, 7.3 Hz), 7.18 (dd, 2H, J 8.0, 7.3 Hz), 6.75 (dd, 1H,
J 7.3, 7.3 Hz), 6.69 (d, 2H, J 8.0 Hz), 4.64 4.60 (m, 1H),
4.60 4.48 (m, 1H), 4.19 (q, 2H, J 7.1 Hz), 3.58 (dd, 1H, J
17.2, 2.2 Hz), 3.54 (d, 1H, J 17.2, 2.2 Hz), 1.20 (t, 3H, J
7.1 Hz); 13C NMR (CDCl3) d 197.26, 172.81, 146.40, 136.42,
133.50, 129.33, 128.67, 128.11, 119.03, 118.52, 114.01, 113.68,
3-(2-Furyl)-1-phenyl-3-(N-phenylamino)-1-propanone
(7p)
Mp 98.0 99.0 8C (ether-hexane); IR (CHCl3): n 3420, 3030,
1
3013, 1686, 1603, 1504, 1362, 1283 cm ; 1H NMR (CDCl3): d
7.92 (dd, 2H, J 7.7, 1.7 Hz), 7.44 (dd, 1H, J 7.7, 7.7 Hz), 7.30
(dd, 2H, J 1.7, 0.7 Hz), 7.24 (s, 1H), 7.15 (dd, 2H, J 8.6,
7.5 Hz), 6.72 (ddd, 1H, J 7.5, 7.5, 1.0 Hz), 6.68 (dd, 2H,
J 8.6, 1.0 Hz), 6.23 (ddd, 2H, J 17.9, 2.4, 0.8 Hz), 5.22 (t, 1H,
J 6.2 Hz), 4.38 (s, 1H), 3.56 (d, 2H, J 6.2 Hz); 13C NMR
(CDCl3): d 197.85, 154.87, 146.57, 141.57, 136.80, 133.29,
129.22, 128.63, 128.02, 118.32, 113.95, 110.35, 106.41, 48.72,
61.52, 52.99, 40.84, 14.06; MS (EI): m/z 297 (M , 14), 224
(16), 105 (100), 77 (63); Anal. found: C 72.66, H 6.61, N 4.68%;
calcd. for C18H19NO3: C 72.71, H 6.44, N 4.71%.
42.34; MS (EI): m/z 291 (M , 13), 172 (68), 105 (100), 77 (78);
3-Cyclohexyl-1-phenyl-3-(N-phenylamino)-1-
propanone (7m)
Anal. found: C 78.19, H 5.68, N 4.98%; calcd. for C19H17NO2:
C 78.33, H 5.88, N, 4.81%.
IR (CHCl3): n 3429, 3034, 3011, 2856, 2934, 1697, 1601, 1506
1
cm ; 1H NMR (CDCl3): d 7.91 (d, 2H, J 7.3 Hz), 7.54 (dd,
1H, J 7.3, 7.3 Hz), 7.43 (dd, 2H, J 7.3, 7.3 Hz), 7.11 (dd, 2H,
J 8.4, 7.3 Hz), 6.63 (dd, 1H, J 7.3, 7.3 Hz), 6.59 (d, 2H, J
8.4 Hz), 3.91 (ddd, 1H, J 5.7, 5.7, 5.7 Hz), 3.83 (br s, 1H), 3.22
(dd, 1H, J 16.7, 5.7 Hz), 3.10 (dd, 1H, J 16.7, 5.7 Hz), 1.98
1.90 (m, 1H), 1.78 1.62 (m, 5H), 1.27 1.13 (m, 5H); 13C NMR
(CDCl3): d 199.43, 147.63, 137.11, 133.04, 129.26, 128.55,
128.00, 117.00, 113.13, 54.68, 41.99, 40.28, 29.81, 29.41, 26.81,
1-Phenyl-3-(N-phenylamino)-3-(2-thienyl)-1-
propanone (7q)
Mp 116.0 117.0 8C (ether-hexane); IR (CHCl3): n 3414,
1
1
3057, 3032, 3011, 1686, 1603, 1504, 1313, 1284 cm ; H NMR
(CDCl3): d 7.93 (d, 2H, J 7.8 Hz), 7.53 (dd, 1H, J 7.8,
7.8 Hz), 7.46 (dd, 2H, J 7.8, 7.8 Hz), 7.13 7.17 (m, 3H), 7.01
(d, 1H, J 3.7 Hz), 6.92 (dd, 1H, J 4.6, 3.7 Hz), 6.73 (dd, 1H,
J 7.7, 7.7 Hz), 6.68 (d, 2H, J 7.7 Hz), 5.38 (d, 1H, J
6.2 Hz), 4.50 (s, 1H), 3.59 (d, 2H, J 6.2 Hz); 13C NMR
(CDCl3): d 197.75, 147.63, 146.59, 136.73, 133.44, 129.20,
128.68, 128.12, 126.86, 124.13, 123.89, 118.38, 114.04, 50.71,
26.28, 26.26; MS (EI): m/z 307 (M , 6), 224 (21), 203 (35), 105
(100), 93 (36), 77 (71); Anal. found: C 82.36, H 8.45, N 4.67%;
calcd. for C21H25NO: C 82.04, H 8.20, N 4.56%.
45.93; MS (EI): m/z 307 (M , 11), 188 (43), 105 (100), 93 (22),
77 (85); Anal. found: C 74.06, H 5.48, N 4.71, S 10.26%; calcd.
for C19H17NOS: C 74.22, H 5.57, N 4.56, S 10.43%.
1,5-Diphenyl-3-(N-phenylamino)-1-pentanone (7n)
IR (CHCl3): n 3429, 3032, 3011, 2928, 2858, 1684, 1601, 1506
1
cm ; 1H NMR (CDCl3): d 7.88 (d, 2H, J 7.3 Hz), 7.55 (dd,
1H, J 7.3, 7.3 Hz), 7.43 (dd, 2H, J 7.3, 7.3 Hz), 7.25 (dd, 2H,
J 4.7, 4.7 Hz), 7.19 7.12 (m, 5H), 6.69 (dd, 1H, J 7.3, 1-Phenyl-3-(N-phenylamino)-1-propanone (7r)
7.3 Hz), 6.59 (d, 2H, J 8.6 Hz), 4.08 3.98 (m, 1H), 3.85 (br s,
Mp 111.0 112.0 8C (ether/hexane); IR (CHCl3): n 3414,
1H), 3.24 (dd, 1H, J 16.6, 4.4 Hz), 3.15 (dd, 1H, J 16.6,
1
3030, 1711, 1603, 1506, 1364, 1232 cm ; 1H NMR (CDCl3): d
6.6 Hz), 2.87 2.61 (m, 2H), 2.06 1.19 (m, 2H); 13C NMR
7.94 (d, 2H, J 7.3 Hz), 7.56 (dd, 1H, J 7.3, 7.3 Hz), 7.45 (dd,
(CDCl3): d 199.30, 147.09, 141.61, 140.19, 137.10, 133.18,
2H, J 7.3, 7.3 Hz), 7.17 (dd, 2H, J 7.5, 7.3 Hz), 6.70 (dd, 1H,
132.05, 129.55, 129.37, 129.10, 128.58, 128.40, 128.37, 128.28,
J 7.3, 7.3 Hz), 6.64 (d, 2H, J 7.5 Hz), 4.10 (br s, 1H), 3.61 (t,
127.99, 125.88, 117.49, 113.42, 49.63, 42.52, 40.69, 36.82, 32.69,
2H, J 6.1 Hz), 3.28 (t, 2H, J 6.1 Hz); 13C NMR(CDCl3): d
26.61; MS (EI): m/z 329 (M , 11), 224 (19), 210 (30), 105
199.24, 147.68, 136.71, 133.30, 129.30, 128.63, 128.00, 117.50,
(100), 91 (65), 77 (76); Anal. found: C 83.68, H 7.06, N 4.25%;
113.01, 38.68, 37.64; MS (EI): m/z 225 (M , 23), 106 (100),
calcd. for C23H23NO: C 83.86, H 7.04, N 4.25%.
105 (20), 93 (10), 77 (52); Anal. found: C 79.71, H 7.01, N 6.30%;
calcd. for C15H15NO: C 79.95, H 6.71, N 6.22%.
4-Benzyloxy-1-phenyl-3-(N-phenylamino)-1-butanone
(7o)
2-Methyl-1,3-diphenyl-3-(N-phenylamino)-1-
propanone (8a)[12]
IR (CHCl3): n 3420, 3032, 3011, 2866, 1668, 1601, 1502, 1364,
1
1258 cm ; 1H NMR (CDCl3): d 7.94 (d, 2H, J 7.7 Hz), 7.55
IR (CHCl3): n 3413, 3059, 3011, 2936, 1680, 1603, 1506, 1317,
1
(dd, 1H, J 7.5, 7.5 Hz), 7.44 (dd, 2H, J 7.7, 7.5 Hz), 7.29
7.24 (m, 5H), 7.16 (dd, 2H, J 8.6, 7.3 Hz), 6.70 (dd, 1H, J 7.3,
7.3 Hz), 6.64 (d, 2H, J 8.6 Hz), 4.50 (Abq, 1H, J 12.1 Hz),
4.48 (Abq, 1H, J 12.1 Hz), 4.30 4.20 (m, 2H), 3.69 3.65 (m,
2H), 3.40 (dd, 1H, J 16.9, 7.6 Hz), 3.23 (dd, 1H, J 16.9,
4.0 Hz); 13C NMR (CDCl3) d 199.38, 146.64, 137.95, 137.10,
133.18, 129.37, 128.56, 128.38, 128.10, 127.71, 127.68, 117.78,
1225 cm ; 1H NMR (CDCl3): d 7.94 7.00 (m, 12H), 6.62
6.44 (m, 3H), 5.07 (major, s, 1H), 4.74 (minor, d, 1H, J
4.9 Hz), 4.71 (major, d, 1H, J 5.9 Hz), 4.46 (minor, s, 1H),
3.97 (minor, dq, 1H, J 6.8, 3.4 Hz), 3.97 (dq, 1H, J 5.9,
3.2 Hz), 1.29 (major, d, 3H, J 7.1 Hz) , 1.22 (minor, d, 3H, J
7.0 Hz); 13C NMR (CDCl3): d 204.04, 202.57, 147.19, 147.13,
141.85, 141.50, 137.14, 136.18, 133.26, 133.10, 129.02, 128.91,
128.76, 128.61, 128.51, 128.25, 128.13, 127.21, 126.80, 126.72,
117.56, 117.18, 113.77, 113.37, 61.09, 59.16, 46.87, 46.44, 16.71,
11.43.
113.64, 73.33, 71.05, 49.63, 39.19; MS (EI): m/z 345 (M , 4),
224 (47), 105 (100), 91 (32), 77 (36); Anal. found: C 79.98, H
6.80, N 4.06%; calcd. for C23H23NO2: C 79.97, H 6.71, N 4.05%.
344
Adv. Synth. Catal. 2002, 344, 338 347