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1
9 8 7 6 5 4 3 2 1 ppm
7.177
7.196
7.215
7.224
7.233
7.243
7.262
7.318
7.337
7.355
7.372
7.495
7.515
7.591
7.610
7.779
7.798
7.867
2.10
3.06
1.06
1.03
2.01
1.00
Signature SIF VIT VELLORENS-A-1
6.87.07.27.47.67.8 ppm
7.177
7.196
7.215
7.224
7.233
7.243
7.262
7.318
7.337
7.355
7.372
7.495
7.515
7.591
7.610
7.779
7.798
7.867
2.10
3.06
1.06
1.03
2.01
1.00
On Water Catalyst-Free Synthesis of Benzo[d]Imidazo[2,1-b] Thiazoles and Novel N-Alkylated 2-
Aminobenzo[d]oxazoles Under Microwave Irradiation
Narasimharao Mukku, and Barnali Maiti*
† Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology,
Vellore-632014, India.
Email: [email protected]
Table of contents Page No
1. Characterization data of compound 3a-5f……………………………………………2-37 2. Supporting data for microwave reaction………………………………………………38
Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2019
2
200 180 160 140 120 100 80 60 40 20 ppm
22.6
7
30.9
431
.60
76.7
477
.06
77.3
8
106.
88
112.
6512
4.40
124.
8912
5.22
126.
2012
7.55
128.
7513
0.32
132.
1613
3.80
147.
6614
8.13
Current Data ParametersNAME NSA1EXPNO 14PROCNO 1
F2 - Acquisition ParametersDate_ 20180209Time 2.00 hINSTRUM spectPROBHD Z108618_0505 (PULPROG zgpg30TD 65536SOLVENT CDCl3NS 512DS 4SWH 24038.461 HzFIDRES 0.733596 HzAQ 1.3631488 secRG 156.91DW 20.800 usecDE 6.50 usecTE 300.0 KD1 2.00000000 secD11 0.03000000 secTD0 1SFO1 100.6550186 MHzNUC1 13CP1 9.80 usecPLW1 58.00000000 WSFO2 400.2596010 MHzNUC2 1HCPDPRG[2 waltz16PCPD2 90.00 usecPLW2 14.00000000 WPLW12 0.35097000 WPLW13 0.17654000 W
F2 - Processing parametersSI 32768SF 100.6449542 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
Signature SIF VIT VELLORENS-A-1
1H and 13C NMR spectrum of compound 3a in CDCl3
S
NN
3a
3
9 8 7 6 5 4 3 2 1 ppm
7.152
7.172
7.242
7.245
7.262
7.280
7.283
7.356
7.359
7.377
7.395
7.397
7.517
7.537
7.616
7.636
7.687
7.707
7.861
3.14
2.06
1.02
1.03
1.01
0.99
1.99
1.01
Signature SIF VIT VELLORENS-A-2
7.37.47.57.67.77.87.9 ppm
7.262
7.280
7.283
7.356
7.359
7.377
7.395
7.397
7.517
7.537
7.616
7.636
7.687
7.707
7.861
2.06
1.02
1.03
1.01
0.99
1.99
1.01
GC MS and IR spectra of compound 3a
S
NN
3a
S
NN
Exact Mass: 250.06
5007501000125015001750200025003000350040001/cm
-0
20
40
60
80
100
%T
3134.33
3047.53
1598.99
1579.70
1490.971438.90
1406.11
1317.38 1292.31
1255.66
1207.44 1145.72
1062.78 1020.34 916.19 85
0.61
775.38
744.52
717.52
648.08
582.50
534.28
501.49
455.20
408.91
NSA-1
S
NN
3a
4
200 180 160 140 120 100 80 60 40 20 ppm
21.2
8
30.9
4
76.7
277
.03
77.3
5
106.
42
112.
6012
4.40
124.
7812
5.12
126.
1712
9.44
130.
3113
1.05
132.
2513
7.33
147.
8414
7.98
Signature SIF VIT VELLORENS-A-2
1H and 13C NMR spectrum of compound 3b in CDCl3
S
NN
3b
5
5007501000125015001750200025003000350040001/cm
-0
20
40
60
80
100
%T
3138.18
1595.13
1550.77
1485.19
1460.11 1400.32
1313.52
1253.73
1201.65
1143.79
1016.49
933.55
821.68
746.45
725.23
694.37
644.22
576.72
503.42
455.20
428.20
NSA-2
9 8 7 6 5 4 3 2 1 ppm
3.852
6.953
6.974
7.311
7.331
7.350
7.428
7.447
7.466
7.583
7.603
7.687
7.707
7.794
7.815
7.878
3.19
1.98
1.00
1.03
0.99
0.98
2.00
1.00
Signature SIF VIT VELLORENSB-13
7.07.27.47.67.8 ppm
6.953
6.974
7.311
7.331
7.350
7.428
7.447
7.466
7.583
7.603
7.687
7.707
7.794
7.815
7.878
1.98
1.00
1.03
0.99
0.98
2.00
1.00
IR spectra of compound 3b
S
NN
3b
6
200 180 160 140 120 100 80 60 40 20 ppm
55.3
5
76.7
277
.04
77.2
477
.35
105.
86
112.
5711
4.16
124.
4012
4.72
126.
1812
6.48
126.
7013
0.25
132.
27
147.
6314
7.94
159.
23
Signature SIF VIT VELLORENSB-13
1H and 13C NMR spectrum of compound 3c in CDCl3
S
NN
OMe
3c
7
5007501000125015001750200025003000350040001/cm
-0
20
40
60
80
100
%T
3126.61
2993.52
2835.36
1608.63
1544.98
1485.19
1398.39
1311.59
1238.30 1105.21
1072.42
1026.13
935.48
831.32
794.67
696.30
642.30
574.79
524.64 426.27
NSB-13
GC MS and IR spectra of compound 3c
S
NN
OMe
3c
8
9 8 7 6 5 4 3 2 1 ppm
1.298
1.316
1.333
4.273
4.290
4.308
4.326
7.461
7.480
7.499
7.551
7.571
7.590
8.035
8.055
8.157
8.177
9.035
3.00
2.05
1.02
1.02
1.02
0.99
1.00
Signature SIF VIT VELLORENSB-5
7.47.67.88.08.28.48.68.89.0 ppm
7.461
7.480
7.499
7.551
7.571
7.590
8.035
8.055
8.157
8.177
9.035
1.02
1.02
1.02
0.99
1.00
200 180 160 140 120 100 80 60 40 20 ppm
14.7
5
39.2
239
.43
39.6
439
.84
40.0
540
.26
40.4
7
60.6
6
114.
8411
9.59
125.
5212
6.67
127.
2813
0.27
131.
7713
7.79
148.
02
162.
31
Signature SIF VIT VELLORENSB-5
1H and 13C NMR spectrum of compound 3d in CDCl3
S
NN
3d
O
O
9
9 8 7 6 5 4 3 2 1 ppm
7.423
7.443
7.463
7.556
7.575
7.595
7.854
7.874
7.960
7.980
8.007
8.027
8.040
8.968
1.04
1.06
2.07
1.05
3.03
1.00
Signature SIF VIT VELLORENSB-15
7.88.08.28.48.68.89.0 ppm
7.463
7.556
7.575
7.595
7.854
7.874
7.960
7.980
8.007
8.027
8.040
8.968
1.04
1.06
2.07
1.05
3.03
1.00
GC MS and IR spectra of compound 3d
S
NN
3d
O
O
10
200 180 160 140 120 100 80 60 40 20 ppm39
.38
39.5
939
.80
40.0
140
.22
40.4
340
.64
109.
6611
1.84
113.
9811
5.29
119.
4912
3.21
125.
5612
6.02
127.
2512
7.67
129.
8113
2.01
133.
2513
8.75
144.
8414
8.18
169.
17
Signature SIF VIT VELLORENSB-15
1H and 13C NMR spectrum of compound 3e in CDCl3
S
NN
CN
3e
S
NN
CN
3e
11
5007501000125015001750200025003000350040001/cm
-0
20
40
60
80
100
%T
3053.32
2220.07
1649.14
1604.77
1544.98
1492.90
1408.04 1317.38
1259.52 1209.37
1149.57
1060.85
1018.41
937.40
867.97
837.11
783.10
744.52
686.66
642.30
547.78
482.20
NSB-15
9 8 7 6 5 4 3 2 1 ppm
7.332
7.350
7.419
7.438
7.466
7.570
7.589
7.691
7.715
7.736
7.920
7.939
8.300
1.09
1.10
2.01
2.02
2.02
1.00
Signature SIF VIT VELLORENSB-7
7.47.67.88.08.28.48.68.8 ppm
7.332
7.350
7.419
7.438
7.466
7.570
7.589
7.691
7.715
7.736
7.920
7.939
8.300
1.09
1.10
2.01
2.02
2.02
1.00
GC MS and IR spectra of compound 3e
12
200 180 160 140 120 100 80 60 40 20 ppm
39.4
739
.69
39.8
940
.10
40.3
140
.52
40.7
4
77.3
677
.69
78.0
1
109.
1111
3.35
124.
5212
5.28
125.
6312
6.67
129.
2012
9.96
131.
8013
6.66
144.
8314
8.16
Signature SIF VIT VELLORENSB-7
1H and 13C NMR spectrum of compound 3f in CDCl3
S
NN
CF3
3f
S
NN
CF3
3f
13
5007501000125015001750200025003000350040001/cm
-0
20
40
60
80
100
%T
2926.01
2497.82
1697.36
1616.35
1496.76
1411.89
1321.24
1259.52
1166.93
1101.35 1068.56
1012.63
933.55
840.96
746.45
713.66 673.16
592.15
501.49
472.56
NSB-7
9 8 7 6 5 4 3 2 1 ppm
7.423
7.426
7.444
7.462
7.550
7.570
7.588
7.986
7.991
8.007
8.011
8.098
8.120
8.244
8.276
1.03
1.03
2.03
2.07
2.04
1.00
Signature SIF VIT VELLORENSB-11
7.47.67.88.08.28.48.68.89.0 ppm
7.423
7.426
7.444
7.462
7.550
7.570
7.588
7.986
7.991
8.007
8.011
8.098
8.120
8.244
8.276
8.298
9.028
1.03
1.03
2.03
2.07
2.04
1.00
GC MS and IR spectra of compound 3f
S
NN
NO2
3g
14
200 180 160 140 120 100 80 60 40 20 ppm39
.43
39.6
439
.85
40.0
640
.27
40.4
840
.69
79.0
179
.34
79.6
7
112.
3511
4.03
124.
6212
5.40
125.
6612
5.99
127.
1412
9.90
140.
8714
4.58
146.
46
Signature SIF VIT VELLORENSB-11
1H and 13C NMR spectrum of compound 3g in CDCl3
15
9 8 7 6 5 4 3 2 1 ppm
1.362
1.380
1.397
2.305
3.944
3.962
3.978
3.995
4.012
4.030
6.904
6.910
6.926
6.932
7.117
7.123
7.141
7.161
7.376
7.396
7.407
7.418
7.664
7.684
7.785
3.00
3.07
2.00
1.00
1.00
1.88
1.03
1.92
1.01
Signature SIF VIT VELLORENSC-2
6.87.07.27.47.67.8 ppm
6.904
6.910
6.926
6.932
7.117
7.123
7.141
7.161
7.376
7.396
7.407
7.418
7.664
7.684
7.785
1.00
1.00
1.88
1.03
1.92
1.01
5007501000125015001750200025003000350040001/cm
-0
20
40
60
80
100
%T3147.83
1689.64
1595.13
1492.90
1456.26
1408.04
1323.17
1259.52
1209.37
1149.57
1103.28
1060.85
937.40
852.54
732.95
680.87
592.15
528.50
474.49
424.34
NSB-11
IR spectra of compound 3g
S
NN
NO2
3g
16
200 180 160 140 120 100 80 60 40 20 ppm
14.8
0
21.2
8
64.3
5
76.7
277
.03
77.3
5
106.
4010
9.41
113.
0711
3.95
125.
0112
6.37
129.
4213
1.09
131.
4413
7.18
147.
2614
7.33
156.
55
Signature SIF VIT VELLORENSC-2
1H and 13C NMR spectrum of compound 3h in CDCl3
S
NN
EtO3h
17
5007501000125015001750200025003000350040001/cm
-0
20
40
60
80
100
%T
2974.23
1600.92
1548.84
1498.691475.54
1394.53
1305.81
1259.52
1244.09
1199.72
1145.72
1111.00
1056.99
1037.70
937.40
825.53
808.17
731.02
700.16
650.01
584.43
503.42
430.13
NSC-2
9 8 7 6 5 4 3 2 1 ppm
1.370
1.388
1.405
3.986
4.003
4.020
4.038
6.863
6.869
6.885
6.891
6.927
6.933
6.949
6.955
7.128
7.134
7.435
7.457
7.567
7.588
7.867
7.887
7.908
7.944
3.04
2.09
1.08
1.00
1.00
2.06
2.07
1.00
Signature SIF VIT VELLORENSC-3
7.27.47.67.88.0 ppm
6.933
6.949
6.955
7.128
7.134
7.435
7.457
7.567
7.588
7.867
7.887
7.908
7.944
1.08
1.00
1.00
2.06
2.07
1.00
HR MS and IR spectra of compound 3h
S
NNO
Exact Mass: 308.09833i
S
NN
EtO3h
18
200 180 160 140 120 100 80 60 40 20 ppm
14.7
7
64.3
8
76.7
177
.03
77.2
377
.35
107.
9310
9.41
113.
3111
4.17
125.
1012
5.70
125.
7412
6.01
128.
9513
1.52
137.
16
145.
4814
7.97
156.
91Signature SIF VIT VELLORENSC-3
1H and 13C NMR spectrum of compound 3i in CDCl3
S
NN
EtO
CF3
3i
19
5007501000125015001750200025003000350040001/cm
-0
20
40
60
80
100
%T
2983.88
1614.42 1579.70
1500.62 1475.541392.61
1317.38
1273.02
1195.87
1161.15
1105.21 1060.85 10
41.56
1012.63
941.26
856.39
833.25
794.67
750.31
713.66 661.58
584.43 505.35
NSC-3
9 8 7 6 5 4 3 2 1 ppm
1.420
1.438
1.455
4.025
4.042
4.060
4.077
6.846
6.852
6.868
6.875
6.881
6.897
6.903
6.932
6.937
6.952
6.958
6.974
6.980
7.157
7.163
7.463
7.485
7.965
7.974
8.137
8.154
8.159
8.176
8.181
3.18
2.13
1.05
2.03
0.98
1.00
1.00
1.04
Current Data ParametersNAME NSC-9EXPNO 67PROCNO 1
F2 - Acquisition ParametersDate_ 20180427Time 23.13 hINSTRUM spectPROBHD Z108618_0505 (PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8012.820 HzFIDRES 0.244532 HzAQ 4.0894465 secRG 127.79DW 62.400 usecDE 6.50 usecTE 301.1 KD1 1.00000000 secTD0 1SFO1 400.2604716 MHzNUC1 1HP1 14.27 usecPLW1 15.00000000 W
F2 - Processing parametersSI 65536SF 400.2580105 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
Signature SIF VIT VELLORENSC-9
HR MS and IR spectra of compound 3i
S
NN
EtO
CF3
3i
20
190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm
14.77
64.33
103.71
103.97
104.23
109.37
110.34
110.49
111.52
111.55
111.73
111.76
113.22
113.95
118.12
118.15
118.24
118.28
126.19
128.72
128.78
128.82
128.87
131.43
139.68
147.11
156.71
158.13
158.25
160.47
160.59
160.62
160.74
162.95
163.07
Current Data ParametersNAME NSC-9EXPNO 68PROCNO 1
F2 - Acquisition ParametersDate_ 20180427Time 23.43 hINSTRUM spectPROBHD Z108618_0505 (PULPROG zgpg30TD 65536SOLVENT CDCl3NS 512DS 4SWH 24038.461 HzFIDRES 0.733596 HzAQ 1.3631488 secRG 199.6DW 20.800 usecDE 6.50 usecTE 301.6 KD1 2.00000000 secD11 0.03000000 secTD0 1SFO1 100.6550186 MHzNUC1 13CP1 9.80 usecPLW1 58.00000000 WSFO2 400.2596010 MHzNUC2 1HCPDPRG[2 waltz16PCPD2 90.00 usecPLW2 15.00000000 WPLW12 0.37709999 WPLW13 0.18968000 W
F2 - Processing parametersSI 32768SF 100.6449542 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
Signature SIF VIT VELLORENSC-9
1H and 13C NMR spectrum of compound 3j in CDCl3
S
NN
EtO
F F
3j
21
5007501000125015001750200025003000350040001/cm
-0
20
40
60
80
100
%T
3057.17
2985.81
2881.65
1618.28
1577.77
1543.05
1496.76
1481.33
1417.68
1392.61
1303.88
1259.521219.01
1184.29 11
14.86
1060.85
1041.56962.48 941.26
844.82 785.03731.02
694.37
603.72
555.50 518.85
466.77
424.34
NSC-9
HR MS and IR spectra of compound 3j
S
NN
EtO
F F
3j
22
9 8 7 6 5 4 3 2 1 ppm
7.308
7.326
7.345
7.441
7.460
7.478
7.871
7.890
8.169
8.191
8.453
8.458
8.475
8.480
8.906
9.118
1.05
2.04
2.03
1.05
1.07
1.00
1.00
Signature SIF VIT VELLORENSB-3
7.47.67.88.08.28.48.68.89.09.2 ppm
7.308
7.326
7.345
7.441
7.460
7.478
7.871
7.890
8.169
8.191
8.453
8.458
8.475
8.480
8.906
9.118
9.123
1.05
2.04
2.03
1.05
1.07
1.00
1.00
200 180 160 140 120 100 80 60 40 20 ppm
39.3
539
.56
39.7
739
.98
40.1
940
.39
40.6
0
110.
1211
4.02
122.
1012
3.16
125.
3212
8.16
129.
3113
1.13
133.
7913
6.43
144.
5714
7.76
149.
34
Signature SIF VIT VELLORENSB-3
1H and 13C NMR spectrum of compound 3k in CDCl3
S
NN
O2N
3k
23
5007501000125015001750200025003000350040001/cm
-0
20
40
60
80
100
%T
3068.75
1685.79
1604.77
1579.70
1519.91
1500.62
1442.751406.11
1332.811309.67
1251.80
1203.58
1143.79
1111.00
1066.64
1026.13
900.76
875.68
813.96
744.52
709.80
686.66
638.44
594.08
551.64 495.71
NSA-3
IR spectra of compound 3k
S
NN
O2N
3k
24
9 8 7 6 5 4 3 2 1 ppm
7.191
7.620
7.640
7.703
7.723
7.915
7.935
7.959
7.979
8.057
8.339
8.344
8.361
8.366
8.620
8.625
2.05
1.00
0.95
0.89
0.95
0.98
0.90
Signature SIF VIT VELLORENSB-8
7.88.08.28.48.68.8 ppm
7.620
7.640
7.703
7.723
7.915
7.935
7.959
7.979
8.057
8.339
8.344
8.361
8.366
8.620
8.625
2.05
1.00
0.95
0.89
0.95
0.98
0.90
200 180 160 140 120 100 80 60 40 20 ppm
65.8
0
76.7
077
.01
77.3
3
108.
2711
2.60
120.
7612
2.51
125.
5812
5.87
125.
9012
6.08
126.
1112
8.10
135.
73
197.
67
Current Data ParametersNAME NSB-8EXPNO 54PROCNO 1
F2 - Acquisition ParametersDate_ 20180324Time 16.38 hINSTRUM spectPROBHD Z108618_0505 (PULPROG zgpg30TD 65536SOLVENT CDCl3NS 512DS 4SWH 24038.461 HzFIDRES 0.733596 HzAQ 1.3631488 secRG 199.6DW 20.800 usecDE 6.50 usecTE 302.8 KD1 2.00000000 secD11 0.03000000 secTD0 1SFO1 100.6550186 MHzNUC1 13CP1 9.80 usecPLW1 58.00000000 WSFO2 400.2596010 MHzNUC2 1HCPDPRG[2 waltz16PCPD2 90.00 usecPLW2 15.00000000 WPLW12 0.37709999 WPLW13 0.18968000 W
F2 - Processing parametersSI 32768SF 100.6449542 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
Signature SIF VIT VELLORENSB-8
1H and 13C NMR spectrum of compound 3l in CDCl3
S
NN
O2N
CF3
3l
25
5007501000125015001750200025003000350040001/cm
-0
20
40
60
80
100
%T
3421.72
3377.36
1681.93 1581.63
1500.62
1415.75
1321.24
1232.51
1166.93
1128.36
1107.14
1064.71
979.84
837.11
763.81
597.93 499.56
428.20
NSB-8
HR MS and IR spectra of compound 3l
S
NN
O2N
CF3
3l
26
9 8 7 6 5 4 3 2 1 ppm
5.602
7.138
7.143
7.163
7.182
7.184
7.204
7.223
7.265
7.287
7.306
7.402
7.420
7.608
7.627
7.646
7.739
7.758
7.776
8.101
8.121
2.00
2.12
1.05
1.04
2.07
1.01
2.03
Current Data ParametersNAME NSREXPNO 45PROCNO 1
F2 - Acquisition ParametersDate_ 20191126Time 23.47 hINSTRUM spectPROBHD Z108618_0505 (PULPROG zg30TD 65536SOLVENT DMSONS 16DS 2SWH 8012.820 HzFIDRES 0.244532 HzAQ 4.0894465 secRG 127.79DW 62.400 usecDE 6.50 usecTE 297.8 KD1 1.00000000 secTD0 1SFO1 400.2604716 MHzNUC1 1HP1 14.00 usecPLW1 16.00000000 W
F2 - Processing parametersSI 65536SF 400.2580000 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
Signature SIF VIT VELLOREMNA-1
7.37.47.57.67.77.8 ppm
7.182
7.184
7.204
7.223
7.265
7.287
7.306
7.402
7.420
7.608
7.627
7.646
7.739
7.758
7.776
180 160 140 120 100 80 60 40 20 ppm
48.83
110.07
110.22
122.90
124.45
128.77
129.44
131.96
134.55
134.78
142.54
154.61
192.73
Current Data ParametersNAME NSREXPNO 46PROCNO 1
F2 - Acquisition ParametersDate_ 20191127Time 0.17 hINSTRUM spectPROBHD Z108618_0505 (PULPROG zgpg30TD 65536SOLVENT DMSONS 512DS 4SWH 24038.461 HzFIDRES 0.733596 HzAQ 1.3631488 secRG 199.6DW 20.800 usecDE 6.50 usecTE 298.3 KD1 2.00000000 secD11 0.03000000 secTD0 1SFO1 100.6550186 MHzNUC1 13CP1 9.80 usecPLW1 58.00000000 WSFO2 400.2596010 MHzNUC2 1HCPDPRG[2 waltz16PCPD2 90.00 usecPLW2 16.00000000 WPLW12 0.38716000 WPLW13 0.19474000 W
F2 - Processing parametersSI 32768SF 100.6449542 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
Signature SIF VIT VELLOREMNA-1
O
N+
5a
NH2
OBr-
1H and 13C NMR spectrum of compound 5a in CDCl3
27
5007501000125015001750200025003000350040001/cm
-0
20
40
60
80
100
%T
2924.09
1766.80
1689.64
1593.20
1487.12 1446.61
1398.39
1355.96
1224.80
1147.65
1089.78
1016.49937.40
906.54869.90
810.10
750.31
684.73663.51626.87
565.14499.56
MNA-1
O
N+
5a
NH2
OBr-
GC MS and IR spectra of compound 5a
28
9 8 7 6 5 4 3 2 1 ppm
3.902
5.190
6.832
6.840
6.848
6.854
6.987
7.009
7.101
7.121
7.130
7.139
7.159
7.228
7.234
7.242
7.250
7.999
8.021
3.01
2.02
1.01
2.01
2.01
0.90
2.00
Signature SIF VIT VELLOREMNA-4
5.56.06.57.07.58.0 ppm
5.190
6.832
6.840
6.848
6.854
6.987
7.009
7.101
7.121
7.130
7.139
7.159
7.228
7.234
7.242
7.250
7.999
2.02
1.01
2.01
2.01
0.90
2.00
200 180 160 140 120 100 80 60 40 20 ppm
47.7
5
55.6
4
108.
7711
0.19
114.
29
122.
7312
3.96
127.
1713
0.58
131.
23
142.
76
154.
77
164.
49
189.
20
Current Data ParametersNAME MNA-4EXPNO 14PROCNO 1
F2 - Acquisition ParametersDate_ 20180522Time 19.46 hINSTRUM spectPROBHD Z108618_0505 (PULPROG zgpg30TD 65536SOLVENT CDCl3NS 512DS 4SWH 24038.461 HzFIDRES 0.733596 HzAQ 1.3631488 secRG 156.91DW 20.800 usecDE 6.50 usecTE 299.1 KD1 2.00000000 secD11 0.03000000 secTD0 1SFO1 100.6550186 MHzNUC1 13CP1 9.80 usecPLW1 58.00000000 WSFO2 400.2596010 MHzNUC2 1HCPDPRG[2 waltz16PCPD2 90.00 usecPLW2 15.00000000 WPLW12 0.37709999 WPLW13 0.18968000 W
F2 - Processing parametersSI 32768SF 100.6449542 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
Signature SIF VIT VELLOREMNA-4
O
N+
5b
NH2
O
OMe
Br-
1H and 13C NMR spectrum of compound 5b in CDCl3
29
5007501000125015001750200025003000350040001/cm
-0
20
40
60
80
100
%T
2972.31
1764.87 1670.35
1600.92
1571.99
1485.19
1425.40
1342.46
1240.23 1174.65
1103.28
1016.49
979.84 910.40
829.39
750.31
736.81684.73628.79
574.79
559.36
499.56
428.20
403.12
MNA-4
O
N+
5b
NH2
O
OMe
Br-
GC MS and IR spectra of compound 5b
30
9 8 7 6 5 4 3 2 1 ppm
5.133
6.748
6.760
6.768
7.064
7.074
7.083
7.170
7.179
7.191
7.436
7.457
7.893
7.913
2.000.992.011.052.012.05
Signature SIF VIT VELLOREMNA-7
5.56.06.57.07.58.0 ppm
5.133
6.748
6.760
6.768
7.064
7.074
7.083
7.170
7.179
7.191
7.436
7.457
7.893
7.913
2.000.992.011.052.012.05
200 180 160 140 120 100 80 60 40 20 ppm
47.9
9
76.7
277
.04
77.3
6
108.
6011
0.33
122.
9412
4.04
129.
5112
9.60
130.
9713
2.41
141.
1014
2.77
154.
66
189.
81
Current Data ParametersNAME MNA-7EXPNO 10PROCNO 1
F2 - Acquisition ParametersDate_ 20180522Time 18.38 hINSTRUM spectPROBHD Z108618_0505 (PULPROG zgpg30TD 65536SOLVENT CDCl3NS 512DS 4SWH 24038.461 HzFIDRES 0.733596 HzAQ 1.3631488 secRG 156.91DW 20.800 usecDE 6.50 usecTE 298.9 KD1 2.00000000 secD11 0.03000000 secTD0 1SFO1 100.6550186 MHzNUC1 13CP1 9.80 usecPLW1 58.00000000 WSFO2 400.2596010 MHzNUC2 1HCPDPRG[2 waltz16PCPD2 90.00 usecPLW2 15.00000000 WPLW12 0.37709999 WPLW13 0.18968000 W
F2 - Processing parametersSI 32768SF 100.6449542 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
Signature SIF VIT VELLOREMNA-7
1H and 13C NMR spectrum of compound 5c in CDCl3
O
N+
5c
O
NH2
Cl
Br-
31
5007501000125015001750200025003000350040001/cm
-0
20
40
60
80
100
%T
2966.52
1759.08 1689.64
1587.42
1485.19
1400.32
1371.39
1242.16
1224.80
1153.43
1087.851020.34
989.48 916.19
871.82
821.68
750.31
680.87
596.00
559.36
524.64
462.92
MNA-7
GC MS and IR spectra of compound 5c
O
NNH
O
Cl
5c286.71
O
N+
5c
O
NH2
Cl
Br-
32
9 8 7 6 5 4 3 2 1 ppm
6.012
7.417
7.434
7.436
7.456
7.475
7.494
7.729
7.747
7.805
7.824
8.054
8.075
8.293
8.313
2.00
2.14
1.01
1.04
2.00
2.05
Signature SIF VIT VELLOREMNA-5
6.57.07.58.0 ppm
6.012
7.417
7.434
7.436
7.456
7.475
7.494
7.729
7.747
7.805
7.824
8.054
2.00
2.14
1.01
1.04
2.00
2.05
180 160 140 120 100 80 60 40 20 ppm
39.22
39.43
39.64
39.85
40.06
40.27
40.48
50.96
111.72
112.07
125.53
126.40
126.64
129.86
130.93
137.43
144.23
159.45
190.42 Current Data Parameters
NAME NEWEXPNO 98PROCNO 1
F2 - Acquisition ParametersDate_ 20181031Time 23.18 hINSTRUM spectPROBHD Z108618_0505 (PULPROG zgpg30TD 65536SOLVENT DMSONS 512DS 4SWH 24038.461 HzFIDRES 0.733596 HzAQ 1.3631488 secRG 199.6DW 20.800 usecDE 6.50 usecTE 298.1 KD1 2.00000000 secD11 0.03000000 secTD0 1SFO1 100.6550186 MHzNUC1 13CP1 9.80 usecPLW1 58.00000000 WSFO2 400.2596010 MHzNUC2 1HCPDPRG[2 waltz16PCPD2 90.00 usecPLW2 16.00000000 WPLW12 0.38716000 WPLW13 0.19474000 W
F2 - Processing parametersSI 32768SF 100.6449542 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
Signature SIF VIT VELLOREMNA-5
O
N+
5d
O
NH2
CF3
Br-
1H and 13C NMR spectrum of compound 5d in CDCl3
33
5007501000125015001750200025003000350040001/cm
-0
20
40
60
80
100
%T
3049.46
2906.73
2652.12
1689.64
1631.78 1591.27
1494.831462.04
1408.041371.39
1311.59 12
26.73
1178.51
1132.211111.00
1062.78 98
9.48
920.05 866.04
837.11
746.45
692.44
659.66 60
3.72
543.93
495.71
MNA-5
O
N+
5d
O
NH2
CF3
Br-
GC MS and IR spectra of compound 5d
34
9 8 7 6 5 4 3 2 1 ppm
5.145
5.154
6.799
6.811
6.821
6.966
6.972
6.993
6.999
7.015
7.021
7.029
7.034
7.051
7.070
7.075
7.121
7.139
7.149
7.158
7.175
7.251
7.263
7.273
8.029
8.050
2.01
1.00
2.08
2.06
1.18
0.99
Current Data ParametersNAME MNA-6EXPNO 11PROCNO 1
F2 - Acquisition ParametersDate_ 20180522Time 18.42 hINSTRUM spectPROBHD Z108618_0505 (PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8012.820 HzFIDRES 0.244532 HzAQ 4.0894465 secRG 175.97DW 62.400 usecDE 6.50 usecTE 298.4 KD1 1.00000000 secTD0 1SFO1 400.2604716 MHzNUC1 1HP1 14.27 usecPLW1 15.00000000 W
F2 - Processing parametersSI 65536SF 400.2580085 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
Signature SIF VIT VELLOREMNA-6
180 160 140 120 100 80 60 40 20 ppm
51.39
51.52
104.75
105.02
105.28
108.37
110.33
113.02
113.05
113.24
113.27
119.07
119.18
122.84
123.95
131.14
133.13
133.18
133.24
133.28
142.80
154.74
162.08
162.20
164.63
164.76
165.49
165.62
168.20
187.52
Current Data ParametersNAME MNA-6EXPNO 12PROCNO 1
F2 - Acquisition ParametersDate_ 20180522Time 19.12 hINSTRUM spectPROBHD Z108618_0505 (PULPROG zgpg30TD 65536SOLVENT CDCl3NS 512DS 4SWH 24038.461 HzFIDRES 0.733596 HzAQ 1.3631488 secRG 156.91DW 20.800 usecDE 6.50 usecTE 299.1 KD1 2.00000000 secD11 0.03000000 secTD0 1SFO1 100.6550186 MHzNUC1 13CP1 9.80 usecPLW1 58.00000000 WSFO2 400.2596010 MHzNUC2 1HCPDPRG[2 waltz16PCPD2 90.00 usecPLW2 15.00000000 WPLW12 0.37709999 WPLW13 0.18968000 W
F2 - Processing parametersSI 32768SF 100.6449542 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
Signature SIF VIT VELLOREMNA-6
O
N+
5e
NH2
O
F
F
Br-
355007501000125015001750200025003000350040001/cm
-0
20
40
60
80
100
%T
3051.39
2935.66
1749.44
1697.36 1612.49 1583.56
1485.19 1411.89
1352.10 1273.02
1238.30
1201.65
1109.07
1022.27
966.34916.19
864.11
817.82
746.45
684.73
596.00
534.28
497.63
430.13
MNA-6
O
N+
5e
NH2
O
F
F
Br-
1H and 13C NMR spectrum of compound 5e in CDCl3
O
N+
5e
NH2
O
F
F
Br-
36
9 8 7 6 5 4 3 2 1 ppm
3.911
5.172
6.839
6.999
7.021
7.089
7.110
7.153
7.174
7.260
7.991
8.012
3.15
2.00
0.90
1.94
1.98
1.92
Current Data ParametersNAME NSREXPNO 47PROCNO 1
F2 - Acquisition ParametersDate_ 20191127Time 0.22 hINSTRUM spectPROBHD Z108618_0505 (PULPROG zg30TD 65536SOLVENT DMSONS 16DS 2SWH 8012.820 HzFIDRES 0.244532 HzAQ 4.0894465 secRG 199.6DW 62.400 usecDE 6.50 usecTE 297.7 KD1 1.00000000 secTD0 1SFO1 400.2604716 MHzNUC1 1HP1 14.00 usecPLW1 16.00000000 W
F2 - Processing parametersSI 65536SF 400.2561087 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
Signature SIF VIT VELLOREMNA-10
7.07.27.47.67.88.0 ppm
6.839
6.999
7.021
7.089
7.110
7.153
7.174
7.260
7.991
8.012
180 160 140 120 100 80 60 40 20 ppm
43.05
50.91
104.64
106.26
109.61
117.93
122.22
124.80
125.85
127.49
136.48
159.88
183.92
Current Data ParametersNAME NSREXPNO 48PROCNO 1
F2 - Acquisition ParametersDate_ 20191127Time 0.52 hINSTRUM spectPROBHD Z108618_0505 (PULPROG zgpg30TD 65536SOLVENT DMSONS 512DS 4SWH 24038.461 HzFIDRES 0.733596 HzAQ 1.3631488 secRG 199.6DW 20.800 usecDE 6.50 usecTE 298.3 KD1 2.00000000 secD11 0.03000000 secTD0 1SFO1 100.6550186 MHzNUC1 13CP1 9.80 usecPLW1 58.00000000 WSFO2 400.2596010 MHzNUC2 1HCPDPRG[2 waltz16PCPD2 90.00 usecPLW2 16.00000000 WPLW12 0.38716000 WPLW13 0.19474000 W
F2 - Processing parametersSI 32768SF 100.6449542 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
Signature SIF VIT VELLOREMNA-10
O
N+
5f
NH2
OBr-
Cl
OMe
GC MS and IR spectra of compound 5e
37
5007501000125015001750200025003000350040001/cm
-0
25
50
75
100
%T
3070.68
2933.73
2843.07
1766.80 1674.21 1598.99 1485.19 14
54.33
1384.89 1344.38
1273.02
1240.231166.931114.86
1064.71
1012.63 989.48 920.05
856.39
831.32
798.53
744.52
680.87
630.72
586.36
561.29
495.71
428.20
MNA-10
1H and 13C NMR spectrum of compound 5f in CDCl3
IR spectra of compound 5f
O
N+
5f
NH2
OBr-
Cl
OMe
38
39
Microwave reactions were carried in Biotage instrument, 2011 model, SW version: 4.1.3. Build 11768
