Supporting Information Component Reaction C3 ...€¦ · s3 170 160 150 140 130 120 110 100 90 80...
Transcript of Supporting Information Component Reaction C3 ...€¦ · s3 170 160 150 140 130 120 110 100 90 80...
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S1
Supporting Information
C3 Functionalization of Indolizines via In(III)-Catalyzed Three-
Component Reaction
Youngeun Jung and Ikyon Kim*
College of Pharmacy and Yonsei Institute of Pharmaceutical Sciences, Yonsei University
85 Songdogwahak-ro, Yeonsu-gu, Incheon 406-840, Republic of Korea
* Corresponding author. Tel.: +82 32 749 4515; fax: +82 32 749 4105; e-mail:
Table of Contents
Copies of 1H and 13C NMR spectra of 2 S2~S30
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2015
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S2
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.02.
16
2.16
3.01
4.19
1.03
1.11
1.16
1.13
2.09
2.71
2.04
1.13
2.01
1.00
1.06
2.20
62.
225
2.24
32.
619
2.63
42.
657
3.64
83.
701
3.71
03.
723
3.73
03.
738
3.74
63.
753
3.76
13.
769
3.77
63.
798
4.70
8
6.73
56.
752
6.76
97.
047
7.06
67.
069
7.08
67.
111
7.12
97.
147
7.18
27.
201
7.22
07.
280
7.35
07.
368
7.40
77.
425
7.44
37.
469
7.48
87.
505
8.20
08.
222
9.02
09.
038
N
CO2Me
N
O
2a
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S3
0102030405060708090100110120130140150160170
50.6
752
.65
66.6
467
.40
102.
64
112.
5212
0.03
122.
4512
2.67
125.
7712
7.32
127.
6112
7.92
128.
4913
2.26
135.
5613
6.26
138.
60
165.
30
N
CO2Me
N
O
2a
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S4
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.02.
15
2.10
3.02
4.27
1.10
1.09
1.22
2.09
4.00
1.21
2.01
1.04
1.06
2.23
02.
246
2.59
82.
613
2.63
3
3.65
03.
700
3.72
23.
729
3.73
83.
747
3.75
63.
765
3.77
23.
793
4.67
0
6.74
66.
763
6.78
07.
062
7.08
17.
084
7.10
17.
129
7.15
07.
315
7.33
67.
348
7.41
17.
429
7.44
77.
470
7.48
87.
506
8.21
38.
235
8.91
78.
935
N
CO2Me
N
O
Br
2b
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S5
0102030405060708090100110120130140150160170
50.7
152
.59
66.1
267
.31
102.
77
112.
7512
0.19
121.
1012
1.73
122.
7912
5.42
127.
4412
8.01
129.
1713
1.63
132.
4013
5.36
136.
3213
7.65
165.
19
N
CO2Me
N
O
Br
2b
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S6
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.02.
16
2.14
3.00
4.51
1.06
1.13
2.25
1.15
1.26
2.08
1.19
1.07
2.15
1.08
1.13
2.23
3
2.62
22.
640
3.65
03.
711
3.74
83.
757
3.77
63.
804
4.68
0
6.76
96.
785
6.80
27.
041
7.06
17.
081
7.10
67.
174
7.19
37.
246
7.26
37.
344
7.36
27.
410
7.43
67.
453
7.48
37.
501
7.51
98.
222
8.24
4
8.90
98.
926
N
CO2Me
N
O Br
2c
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S7
0102030405060708090100110120130140150160170
50.6
852
.57
66.1
767
.27
102.
78
112.
8112
0.14
121.
6012
2.62
122.
8312
5.33
126.
0212
7.45
128.
0113
0.04
130.
4213
0.47
132.
4713
5.30
136.
3114
0.96
165.
15
N
CO2Me
N
O Br
2c
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S8
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.02.
07
2.10
3.00
4.28
1.06
1.08
4.14
1.05
2.04
1.11
2.05
1.03
1.04
2.23
4
2.62
7
3.65
13.
711
3.73
93.
748
3.76
13.
768
3.77
73.
783
3.80
6
4.69
0
6.76
66.
782
6.79
97.
066
7.08
77.
118
7.27
27.
347
7.36
57.
435
7.45
37.
481
7.50
07.
518
8.22
18.
244
8.90
88.
926
N
CO2Me
N
O Cl
2d
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S9
0102030405060708090100110120130140150160170
50.6
952
.58
66.1
767
.28
102.
78
112.
8112
0.14
121.
6312
2.83
125.
3612
5.67
127.
4512
7.51
128.
0112
9.75
132.
4813
4.37
135.
3113
6.31
140.
71
165.
16
N
CO2Me
N
O Cl
2d
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S10
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.02.
09
2.09
3.04
4.21
1.03
1.14
1.14
2.02
2.16
0.93
2.02
2.00
1.11
1.05
2.28
92.
307
2.62
22.
631
2.63
82.
660
3.65
83.
736
3.75
83.
765
3.77
33.
781
3.78
93.
796
3.80
53.
812
3.83
4
4.84
6
6.77
56.
792
6.80
97.
083
7.10
17.
105
7.12
27.
360
7.37
87.
429
7.45
17.
460
7.47
87.
504
7.52
37.
540
8.06
08.
082
8.22
68.
249
8.83
98.
857
N
CO2Me
N
O
NO2
2e
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S11
0102030405060708090100110120130140150160170
50.7
852
.58
66.1
367
.22
103.
08
113.
1412
0.38
120.
6112
3.07
123.
8012
4.93
127.
6712
8.16
132.
8513
5.07
136.
49
145.
9514
7.07
165.
04
N
CO2Me
N
O
NO2
2e
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S12
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.02.
16
2.21
3.20
7.74
1.09
2.13
1.00
1.17
2.16
2.19
1.23
2.12
1.16
1.17
2.21
1
2.61
0
3.64
53.
689
3.71
23.
726
3.73
53.
744
3.75
23.
760
3.77
23.
781
4.64
2
6.72
76.
749
7.16
47.
186
7.33
17.
348
7.41
57.
433
7.45
77.
476
8.20
28.
225
9.04
49.
061
N
CO2Me
N
O
OMe
2f
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S13
0102030405060708090100110120130140150160170
50.6
352
.63
55.3
0
66.1
767
.39
102.
54
112.
4511
3.85
120.
0312
2.56
122.
8012
5.80
127.
2512
7.87
128.
6213
0.73
132.
0213
5.60
136.
20
158.
71
165.
30
N
CO2Me
N
O
OMe
2f
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S14
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.02.
08
2.15
3.03
3.10
4.01
1.06
1.06
2.00
1.04
1.12
1.05
2.08
1.05
2.04
1.08
1.08
2.22
52.
243
2.65
12.
672
3.64
73.
687
3.72
13.
727
3.73
63.
743
3.75
13.
758
3.76
73.
774
3.79
5
4.68
26.
653
6.65
76.
673
6.67
86.
739
6.75
96.
769
6.88
66.
905
7.04
57.
066
7.08
47.
093
7.11
37.
133
7.36
17.
379
7.41
97.
437
7.46
47.
482
7.50
0
8.20
18.
224
9.02
29.
039
N
CO2Me
N
O OMe
2g
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S15
0102030405060708090100110120130140150160170
50.6
552
.64
55.2
1
66.6
167
.38
102.
61
112.
5311
2.62
113.
4511
9.72
120.
0212
2.30
122.
6812
5.82
127.
3312
7.90
129.
3913
2.22
135.
5913
6.27
140.
21
159.
63
165.
27
N
CO2Me
N
O OMe
2g
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S16
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.02.
19
2.13
3.00
10.1
5
1.06
1.10
1.11
1.14
1.17
1.18
5.49
1.14
1.14
2.24
2
2.65
3
3.65
13.
721
3.73
93.
753
3.76
83.
783
3.80
3
4.64
0
6.57
06.
704
6.72
56.
753
6.76
96.
786
6.95
26.
955
6.97
36.
976
7.05
37.
071
7.07
57.
092
7.37
57.
402
7.42
07.
438
7.47
78.
212
8.23
5
9.09
19.
108
N
CO2Me
N
O OMe
OMe
2h
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S17
0102030405060708090100110120130140150160170
50.6
252
.65
55.7
855
.89
66.5
667
.34
102.
52
110.
8411
1.23
112.
4211
8.81
120.
0612
2.56
122.
6512
5.78
127.
3013
1.14
131.
8813
5.67
136.
23
148.
0514
8.85
165.
23
N
CO2Me
N
O OMe
OMe
2h
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S18
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0
2.00
3.29
2.33
3.32
4.53
1.22
1.24
2.18
1.26
2.30
2.23
1.26
2.19
1.16
1.15
2.23
4
2.61
83.
643
3.68
93.
698
3.71
13.
718
3.72
63.
733
3.74
13.
748
3.75
73.
764
3.78
5
4.66
2
6.73
36.
736
6.75
26.
767
6.77
06.
997
7.01
77.
041
7.05
87.
061
7.08
07.
140
7.16
07.
337
7.35
47.
400
7.41
97.
437
7.46
17.
480
7.49
68.
194
8.21
6
9.05
19.
068
N
CO2Me
N
O
Me
2i
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S19
0102030405060708090100110120130140150160170
21.1
0
50.6
452
.64
66.5
067
.40
102.
58
112.
4312
0.02
122.
5912
2.65
125.
8812
7.26
127.
4912
7.87
129.
1713
2.12
135.
6113
6.23
136.
96
165.
31
N
CO2Me
N
O
Me
2i
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S20
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.02.
13
2.09
3.00
4.39
1.06
1.09
1.12
1.12
3.71
1.42
2.15
1.15
3.23
1.15
1.13
2.29
12.
308
2.70
42.
727
3.64
53.
757
3.76
33.
773
3.77
93.
798
3.80
53.
814
3.82
1
4.88
06.
750
7.04
37.
299
7.32
07.
383
7.40
27.
405
7.40
97.
414
7.42
47.
459
7.47
77.
505
7.52
37.
639
7.66
17.
698
7.72
17.
744
7.75
4
8.18
88.
211
9.10
79.
125
N
CO2Me
N
O
2j
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S21
0102030405060708090100110120130140150160170
50.6
552
.72
66.8
067
.39
102.
66
112.
5912
0.05
122.
1712
2.68
125.
6912
5.85
125.
9512
6.04
126.
2412
7.38
127.
6212
7.97
128.
2713
2.39
132.
6913
3.14
135.
5813
6.00
136.
30
165.
24
N
CO2Me
N
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S44
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0
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S45
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S50
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S56
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0
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