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–1
δ = 167.0, 162.4, 138.6, 128.9, 128.9, 128.0, 127.7, 126.8, 113.9, 55.5, ν˜ = 2971, 2928, 1723, 1632, 1605, 1503, 1252, 1027, 767 cm . LRMS
+
4
4.2 ppm. The analytical data are in agreement with previously re- (ESI): m/z 282 [M + H ]. HRMS (ESI-TOF): m/z calcd. for
[
28]
1
+
ported ones.
3-Chlorobenzonitrile (8e): H NMR (400 MHz,
C H NNaO : 304.1519, found 304.1522.
15 23 4
CDCl ): δ = 7.64 (t, J = 1.6 Hz, 1H), 7.61–7.57 (m, 1H), 7.56 (td, J =
3
4
-Methoxy-N-octylbenzamide (7h). According to the general pro-
cedure E using 2,2-diazido-1-(4-methoxyphenyl)-2-phenylethanone
6f, 60 mg, 0.19 mmol, 1.0 eq.) and octylamine (32 mg, 0.24 mmol,
.25 eq.), 4-methoxy-N-octylbenzamide (7h, 46 mg, 0.17 mmol,
1
3
7
.8, 1.3 Hz, 1H), 7.43 (t, J = 7.9 Hz, 1H) ppm. C NMR (101 MHz,
CDCl ): δ = 135.4, 133.4, 132.1, 130.6, 130.4, 117.6, 114.2 ppm. The
3
(
1
[
32]
analytical data are in agreement with previously reported ones.
N-Benzyl-4-methoxybenzamide (7e) and Benzonitrile (8a). Ac-
cording to the general procedure D using 2,2-diazido-1-(4-methoxy-
phenyl)-2- phenylethanone (6f, 120 mg, 0.39 mmol, 1.0 eq.), N-
benzyl-4-methoxybenzamide (7e, 85 mg, 0.35 mmol, 91 %) and (s, 3H), 3.44–3.38 (m, 2H), 1.62–1.56 (m, 2H), 1.37–1.24 (m, 10H), 0.87
benzonitrile (8a, 26 mg, 0.25 mmol, 65 %) were obtained after chro-
90 %) was obtained after chromatography (PE/EtOAc, 9:1 → 6:4) as
1
a white solid. R (PE/EtOAc, 1:1) = 0.31 [UV]. H NMR (600 MHz,
f
CDCl ): δ = 7.76–7.69 (m, 2H), 6.94–6.87 (m, 2H), 6.14 (s, 1H), 3.83
3
(t, J = 7.1 Hz, 3H) ppm. 13C NMR (151 MHz, CDCl ): δ = 167.2,
3
matography (PE → PE/EtOAc, 6:4). N-Benzyl-4-methoxybenzamide
162.2, 128.7, 127.3, 113.8, 55.5, 40.2, 31.9, 29.9, 29.4, 29.3, 27.2, 22.8,
14.2 ppm. The analytical data are in agreement with previously re-
1
(
7e): H NMR (400 MHz, CDCl ): δ = 7.81–7.73 (m, 2H), 7.40–7.27 (m,
3
[
35]
5
3
1
H), 6.98–6.86 (m, 2H), 6.39 (s, 1H), 4.63 (d, J = 5.7 Hz, 2H), 3.84 (s,
ported ones.
H) ppm. 13C NMR (101 MHz, CDCl ): δ = 167.0, 162.4, 138.6, 128.9,
3
N-Cyclohexyl-4-methoxybenzamide (7i). According to the general
procedure E using 2,2-diazido-1-(4-methoxyphenyl)-2-phenyl-
ethanone (6f, 60 mg, 0.19 mmol, 1.0 eq.) and cyclohexylamine
(32 mg, 0.24 mmol, 1.25 eq.), N-cyclohexyl-4-methoxybenzamide
28.9, 128.0, 127.7, 126.8, 113.9, 55.5, 44.2 ppm. The analytical data
[
28]
are in agreement with previously reported ones.
Benzonitrile
1
(8a): H NMR (600 MHz, CDCl ): δ = 7.68–7.63 (m, 2H), 7.63–7.58 (m,
3
1
3
1
H), 7.50–7.45 (m, 2H) ppm. C NMR (151 MHz, CDCl ): δ = 132.7,
3
(
7i, 39 mg, 0.17 mmol, 86 %) was obtained after chromatography
(PE/EtOAc, 9:1 → 6:4) as a white solid. R (PE/EtOAc, 1:1) = 0.28 [UV].
H NMR (600 MHz, CDCl ): δ = 7.75–7.69 (m, 2H), 6.94–6.89 (m, 2H),
1
32.1, 129.1, 118.8, 112.5 ppm. The analytical data are in agreement
[27]
f
with previously reported ones.
1
3
N-Benzyl-4-methoxybenzamide (7e) and 4-Pentylbenzonitrile
8f). According to the general procedure D using 2,2-diazido-1-(4-
methoxyphenyl)-2-(4-pentylphenyl)ethanone (6g, 40 mg,
5.87 (d, J = 6.3 Hz, 1H), 4.01–3.92 (m, 1H), 3.84 (s, 3H), 2.07–1.99 (m,
(
2
1
1
H), 1.80–1.72 (m, 2H), 1.69–1.64 (m, 1H), 1.50–1.39 (m, 2H), 1.26–
13
.20 (m, 3H) ppm. C NMR (151 MHz, CDCl ): δ = 166.3, 162.2,
3
0
0
7
.11 mmol, 1.0 eq.), N-benzyl-4-methoxybenzamide (7e, 18 mg,
.07 mmol, 71 %) and 4-pentylbenzonitrile (8f, 14 mg, 0.08 mmol,
28.7, 127.6, 113.8, 55.5, 48.7, 33.5, 25.8, 25.1 ppm. The analytical
[36]
data are in agreement with previously reported ones.
6 %) were obtained after chromatography (PE → PE/EtOAc, 6:4).
1
N-((1R,2S)-2-Hydroxy-2,3-dihydro-1H-inden-1-yl)-4-methoxy-
benzamide (7j). According to the general procedure E using 2,2-
diazido-1-(4-methoxyphenyl)-2-phenylethanone (6f, 60 mg,
N-Benzyl-4-methoxybenzamide (7e): H NMR (400 MHz, CDCl ): δ =
3
7
4
.81–7.73 (m, 2H), 7.40–7.27 (m, 5H), 6.98–6.86 (m, 2H), 6.39 (s, 1H),
.63 (d, J = 5.7 Hz, 2H), 3.84 (s, 3H) ppm. C NMR (101 MHz, CDCl3):
1
3
0.19 mmol, 1.0 eq.) and (1R,2S)-(+)-cis-1-amino-2-indanol (37 mg,
δ = 167.0, 162.4, 138.6, 128.9, 128.9, 128.0, 127.7, 126.8, 113.9, 55.5,
4.2 ppm. The analytical data are in agreement with previously re-
0.24 mmol, 1.25 eq.), N-((1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-
4
[28]
1
yl)-4-methoxybenzamide (7j, 32 mg, 0.11 mmol, 58 %) was obtained
ported ones. 4-Pentylbenzonitrile (8f): H NMR (600 MHz, CDCl ):
3
after chromatography (PE/EtOAc, 8:2 → 6:4) as a white solid. R (PE/
δ = 7.59 (d, J = 8.3 Hz, 2H), 7.32–7.28 (m, 2H), 2.69 (t, J = 7.6 Hz,
f
1
EtOAc, 1:1) = 0.24 [UV]. H NMR (600 MHz, CDCl ): δ = 7.83–7.79
2
H), 1.69–1.62 (m, 2H), 1.40–1.31 (m, 4H), 0.92 (t, J = 7.1 Hz, 3H)
3
13
(m, 2H), 7.37–7.33 (m, 1H), 7.31–7.28 (m, 2H), 7.27–7.22 (m, 1H),
ppm. C NMR (151 MHz, CDCl ): δ = 148.7, 132.2, 129.3, 119.3,
3
6.94–6.90 (m, 2H), 6.86 (d, J = 8.1 Hz, 1H), 5.57 (dd, J = 8.2, 5.2 Hz,
1
09.7, 36.2, 31.5, 30.8, 22.6, 14.1 ppm. The analytical data are in
[33]
1H), 4.72 (td, J = 5.2, 2.1 Hz, 1H), 3.87 (s, 3H), 3.23 (dd, J = 16.5,
agreement with previously reported ones.
1
3
5
.2 Hz, 1H), 3.01 (dd, J = 16.5, 1.9 Hz, 1H), 2.74 (s, 1H) ppm. C NMR
N-(Benzo[d][1,3]dioxol-5-ylmethyl)-4-methoxybenzamide (7f).
According to the general procedure E using 2,2-diazido-1-(4-meth-
oxyphenyl)-2-phenylethanone (6f, 60 mg, 0.19 mmol, 1.0 eq.) and
piperonylamine (38 mg, 0.24 mmol, 1.25 eq.), N-(benzo[d][1,3]di-
oxol-5-ylmethyl)-4-methoxybenzamide (7f, 46 mg, 0.16 mmol, 83 %)
was obtained after chromatography (PE/EtOAc, 9:1 → 1:1) as a
(
151 MHz, CDCl ): δ = 167.5, 162.4, 140.9, 140.0, 129.0, 128.2, 127.2,
3
1
3
26.3, 125.3, 124.7, 113.8, 73.7, 57.9, 55.4, 39.9 ppm. IR (ATR): ν˜ =
–1
417, 3256, 2920, 1610, 1537, 1461, 1252, 1023 cm . LRMS (ESI):
+
+
m/z 284 [M + H ]. HRMS (ESI-TOF): m/z calcd. for C H NNaO :
17
17
3
306.1101, found 306.1110.
1
white solid. R (PE/EtOAc, 6:4) = 0.23 [UV]. H NMR (600 MHz, CDCl ):
4-Methoxy-N-(phenylbutyl)benzamide (7k). According to the
general procedure E using 2,2-diazido-1-(4-methoxyphenyl)-2-
phenylethanone (6f, 70 mg, 0.20 mmol, 1.0 eq.) and 4-phenylbutyl-
amine (38 mg, 0.26 mmol, 1.25 eq.), 4-methoxy-N-(4-phenyl-
butyl)benzamide (7k, 45 mg, 0.16 mmol, 78 %) was obtained after
f
3
δ = 7.78–7.72 (m, 2H), 6.93–6.86 (m, 2H), 6.83–6.73 (m, 3H), 6.48 (s,
H), 5.92 (s, 2H), 4.50 (d, J = 5.7 Hz, 2H), 3.82 (s, 3H) ppm. 13C NMR
151 MHz, CDCl ): δ = 167.0, 162.3, 148.1, 147.1, 132.5, 128.9, 126.8,
1
(
3
1
21.3, 113.9, 108.6, 108.4, 101.2, 55.5, 44.0 ppm. The analytical data
[34]
are in agreement with previously reported ones.
chromatography (CH:EtOAc 9:1 → 4:6) as a white solid. R (PE/EtOAc,
f
1
1
7
3
4
1
:1) = 0.26 [UV]. H NMR (400 MHz, CDCl ): δ = 7.73–7.58 (m, 2H),
3
N-(3,3-Diethoxypropyl)-4-methoxybenzamide (7g). According to
the general procedure E using 2,2-diazido-1-(4-methoxyphenyl)-2-
phenylethanone (6f, 60 mg, 0.19 mmol, 1.0 eq.) and 3,3-diethoxy-
propan-1-amine (36 mg, 0.24 mmol, 1.25 eq.), N-(3,3-diethoxy-
propyl)-4-methoxybenzamide (7g, 46 mg, 0.16 mmol, 84 %) was ob-
tained after chromatography (PE/EtOAc, 8:2 → 6:4) as a white solid.
.29–7.24 (m, 2H), 7.20–7.14 (m, 3H), 6.95–6.83 (m, 2H), 6.19 (s, 1H),
.82 (s, 3H), 3.47–3.39 (m, 2H), 2.64 (t, J = 7.3 Hz, 2H), 1.76–1.56 (m,
H) ppm. 13C NMR (101 MHz, DMSO): δ = 167.2, 162.2, 142.2, 128.8,
28.5, 128.5, 127.1, 125.9, 113.8, 55.5, 40.0, 35.6, 29.4, 28.8 ppm. IR
(
6
ATR): ν = 2938, 2857, 1631, 1605, 1532, 1245, 1178, 1025, 845, 767,
˜
–
1
+
07 cm . LRMS (ESI): m/z 284 [M + H ]. HRMS (ESI-TOF): m/z calcd.
1
R (PE/EtOAc, 6:4) = 0.14 [UV]. H NMR (600 MHz, CDCl ): δ = 7.75–
f
3
+
for C H NNaO : 306.1464, found 306.1466.
18
21
2
7
3
7
1
.70 (m, 2H), 6.95–6.88 (m, 3H), 4.63 (t, J = 5.0 Hz, 1H), 3.83 (s, 3H),
.76–3.67 (m, 2H), 3.59–3.49 (m, 4H), 1.96–1.91 (m, 2H), 1.23 (t, J = N-(4-(((8R,9S,13S,14S,17S)-3,17-Dihydroxy-13-methyl-
.1 Hz, 6H) ppm. 13C NMR (151 MHz, CDCl ): δ = 166.8, 162.2, 128.7,
7,8,9,11,12,13,14,15,16,17-decahydro –6H-cyclopenta[a]phen-
anthren-17-yl)ethynyl)benzyl)-4-methoxybenzamide (7l). Ac-
3
27.3, 113.8, 103.2, 62.3, 55.5, 36.1, 33.0, 15.5 ppm. IR (ATR):
Eur. J. Org. Chem. 0000, 0–0
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