new journal of chemistry · 2013. 11. 29. · new journal of chemistry page 1 of 63 new journal of...
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New Journal of Chemistry
Page 1 of 63
New Journal of Chemistry
Cycloalkenyl nonaflates as electrophilic cross-coupling substrates for palladium catalyzed C-N
bond forming reactions with enolizable heterocycles under microwave enhanced conditions
K. K. Abdul Khadera, Ayyiliath. M. Sajith
b,c*, M. Syed Ali Padusha
a* H. P. Nagaswarupa
d, A. Muralidharan
b,c
Table of contents
1. 1H NMR spectra of 3-oxocyclopent-1-enyl trifluoromethanesulfonate .............................................................................................. 5
2. 13 C NMR Spectra of 3-oxocyclopent-1-enyl trifluoromethanesulfonate .......................................................................................... 6
3. 19 F NMR Spectra of 3-oxocyclopent-1-enyl trifluoromethanesulfonate ........................................................................................... 7
4. 1H NMR Spectra of 3-oxocyclopent-1-enyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate ............................................................ 8
5. 13 C NMR Spectra of 3-oxocyclopent-1-enyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate ......................................................... 9
6. 19 F NMR Spectra of 3-oxocyclopent-1-enyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate ....................................................... 10
7. 1 H NMR Spectra of 3-oxocyclohex-1-enyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate .......................................................... 11
8. 13 C NMR Spectra of 3-oxocyclohex-1-enyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate ........................................................ 12
9. 1 H NMR spectra of 5-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5a ......................................................................... 13
10. 13 C NMR spectra of 5-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5a .................................................................... 14
11. IR spectra of 5-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5a ................................................................................. 15
12. LCMS spectra of 5-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5a .......................................................................... 16
13. 1 H NMR spectra of 4-methyl-3-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5b ......................................................... 17
14. 13 C NMR spectra of 4-methyl-3-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5b ....................................................... 18
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New Journal of Chemistry
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15. IR spectra of 4-methyl-3-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5b ..................................................................... 19
16. LCMS spectra of 4-methyl-3-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5b .............................................................. 20
17. 1 H NMR Spectra of 1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5c .................................................................................... 21
18. 13 C NMR Spectra of 1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5c ................................................................................... 22
19. IR Spectra of 1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5c ................................................................................................ 23
20. LCMS Spectra of 1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5c .......................................................................................... 24
21. 1 H NMR Spectra of 3-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5d .................................................................... 25
22. 13 C NMR Spectra of 3-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5d ................................................................... 26
23. LCMS Spectra of 3-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5d .......................................................................... 27
24. 1 H NMR Spectra of 4-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5e ..................................................................... 28
25. 13 C NMR Spectra of 4-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5e ................................................................... 29
26. IR Spectra of 4-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5e ................................................................................. 30
27. LCMS Spectra of 4-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5e ......................................................................... 31
28. 1 H NMR Spectra of 5-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5f ......................................................................... 32
29. 13 CNMR Spectra of 5-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5f ........................................................................ 33
30. IR Spectra of 5-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5f ..................................................................................... 34
31. 1 H NMR Spectra of 1, 3-bis (3-oxocyclopent-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5i ................................................... 35
32. 13 C NMR Spectra of 1, 3-bis (3-oxocyclopent-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5i ................................................. 36
33. IR Spectra of 1, 3-bis (3-oxocyclopent-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5i ............................................................... 37
34. LCMS Spectra of 1, 3-bis (3-oxocyclopent-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5i ........................................................ 38
35. 1 H NMR Spectra of 3-chloro-7-(3-oxocyclopent-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5k ..................................................... 39
36. 13 C NMR Spectra of 3-chloro-7-(3-oxocyclopent-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5k ................................................... 40
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37. IR Spectra of 3-chloro-7-(3-oxocyclopent-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5k ................................................................. 41
38. LCMS Spectra of 3-chloro-7-(3-oxocyclopent-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5k ......................................................... 42
39. 1 H NMR Spectra of 1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5m .................................................................................... 43
40. 13 C NMR Spectra of 1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5m .................................................................................. 44
41. IR Spectra of 1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5m ................................................................................................ 45
42. LCMS Spectra of 1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5m ......................................................................................... 46
43. 1 H NMR Spectra of 5-methyl-1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5o ...................................................................... 47
44. 13 C NMR Spectra of 5-methyl-1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5o .................................................................... 48
45. LCMS Spectra of 5-methyl-1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5o ........................................................................... 49
46. 1 H NMR Spectra of 4-(trifluoromethyl)-1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5p ...................................................... 50
47. LCMS Spectra of 4-(trifluoromethyl)-1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5p .......................................................... 51
48. 1 H NMR Spectra of 1-(3-oxocyclohex-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5q ............................................................. 52
49. LCMS Spectra of 1-(3-oxocyclohex-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5q .................................................................. 53
50. IR Spectra of 1-(3-oxocyclohex-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5q ......................................................................... 54
51. 1 H NMR Spectra of 3-methoxy-7- (3-oxocyclohex-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5s .................................................. 55
52. 13 C NMR Spectra of 3-methoxy-7- (3-oxocyclohex-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5s ................................................ 56
53. IR Spectra of 3-methoxy-7- (3-oxocyclohex-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5s .............................................................. 57
54. LCMS Spectra of 3-methoxy-7- (3-oxocyclohex-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5s ....................................................... 58
55. 1 H NMR Spectra of 1-(5,5-dimethyl-3-oxocyclohex-1-enyl)pyridin-2(1H)-one, 5t ................................................................... 59
56. 13 C NMR Spectra of 1-(5,5-dimethyl-3-oxocyclohex-1-enyl)pyridin-2(1H)-one, 5t .................................................................. 60
57. LCMS Spectra of 1-(5,5-dimethyl-3-oxocyclohex-1-enyl)pyridin-2(1H)-one, 5t ........................................................................ 61
58. LCMS Spectra of 1-(3-oxo-5-phenylcyclohex-1-enyl)pyridin-2(1H)-one, 5u .............................................................................. 62
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59. LCMS Spectra of 1-(5-(4-chlorophenyl)-3-oxocyclohex-1-enyl)pyridin-2(1H)-one, 5v .............................................................. 63
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1. 1H NMR spectra of 3-oxocyclopent-1-enyl trifluoromethanesulfonate
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2. 13 C NMR Spectra of 3-oxocyclopent-1-enyl trifluoromethanesulfonate
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3. 19 F NMR Spectra of 3-oxocyclopent-1-enyl trifluoromethanesulfonate
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4. 1H NMR Spectra of 3-oxocyclopent-1-enyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate
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5. 13 C NMR Spectra of 3-oxocyclopent-1-enyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate
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6. 19 F NMR Spectra of 3-oxocyclopent-1-enyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate
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7. 1 H NMR Spectra of 3-oxocyclohex-1-enyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate
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8. 13 C NMR Spectra of 3-oxocyclohex-1-enyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate
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9. 1 H NMR spectra of 5-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5a
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10. 13 C NMR spectra of 5-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5a
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11. IR spectra of 5-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5a
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IR Report
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4000 3500 3000 2500 2000 1500 1000 500
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12. LCMS spectra of 5-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5a
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13. 1 H NMR spectra of 4-methyl-3-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5b
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14. 13 C NMR spectra of 4-methyl-3-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5b
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15. IR spectra of 4-methyl-3-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5b
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16. LCMS spectra of 4-methyl-3-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5b
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17. 1 H NMR Spectra of 1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5c
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18. 13 C NMR Spectra of 1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5c
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19. IR Spectra of 1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5c
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20. LCMS Spectra of 1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5c
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21. 1 H NMR Spectra of 3-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5d
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22. 13 C NMR Spectra of 3-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5d
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23. LCMS Spectra of 3-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5d
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24. 1 H NMR Spectra of 4-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5e
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25. 13 C NMR Spectra of 4-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5e
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26. IR Spectra of 4-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5e
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27. LCMS Spectra of 4-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5e
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28. 1 H NMR Spectra of 5-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5f
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29. 13 CNMR Spectra of 5-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5f
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30. IR Spectra of 5-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5f
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31. 1 H NMR Spectra of 1, 3-bis (3-oxocyclopent-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5i
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32. 13 C NMR Spectra of 1, 3-bis (3-oxocyclopent-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5i
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33. IR Spectra of 1, 3-bis (3-oxocyclopent-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5i
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34. LCMS Spectra of 1, 3-bis (3-oxocyclopent-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5i
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35. 1 H NMR Spectra of 3-chloro-7-(3-oxocyclopent-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5k
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36. 13 C NMR Spectra of 3-chloro-7-(3-oxocyclopent-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5k
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37. IR Spectra of 3-chloro-7-(3-oxocyclopent-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5k
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38. LCMS Spectra of 3-chloro-7-(3-oxocyclopent-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5k
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39. 1 H NMR Spectra of 1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5m
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40. 13 C NMR Spectra of 1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5m
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41. IR Spectra of 1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5m
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42. LCMS Spectra of 1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5m
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43. 1 H NMR Spectra of 5-methyl-1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5o
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44. 13 C NMR Spectra of 5-methyl-1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5o
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45. LCMS Spectra of 5-methyl-1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5o
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46. 1 H NMR Spectra of 4-(trifluoromethyl)-1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5p
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47. LCMS Spectra of 4-(trifluoromethyl)-1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5p
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48. 1 H NMR Spectra of 1-(3-oxocyclohex-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5q
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49. LCMS Spectra of 1-(3-oxocyclohex-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5q
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50. IR Spectra of 1-(3-oxocyclohex-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5q
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847.3
808.2
775.6
746.1
727.0
690.5
654.3
604.8
539.6
IR Report
100
95
90
85
80
75
70
65
60
55
50
45
40
4000
3500
3000
2500
2000
1500
1000
Wavenumbers (cm-1)
Electronic Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013
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New Journal of Chemistry
Page 55 of 63
51. 1 H NMR Spectra of 3-methoxy-7- (3-oxocyclohex-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5s
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New Journal of Chemistry
Page 56 of 63
52. 13 C NMR Spectra of 3-methoxy-7- (3-oxocyclohex-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5s
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New Journal of Chemistry
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53. IR Spectra of 3-methoxy-7- (3-oxocyclohex-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5s
Wed Feb 27 11:57:55 2013 (GMT+05:30
%T
ran
smitt
an
ce
3059.5
2937.2
1660.3
1617.2
1591.1
1479.0
1453.3
1417.6
1345.6
1309.3
1227.3
1171.2
1133.1
1109.7
1063.7
1038.9
1011.1
961.4
895.3
849.3
808.2
782.7
756.8
734.0
691.1
620.3
532.1
502.2
440.3
IR Report
100
90
80
70
60
50
40
30
20
10
0
4000 3500 3000 2500 2000 1500 1000 500
Wavenumbers (cm-1)
Electronic Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013
-
New Journal of Chemistry
Page 58 of 63
54. LCMS Spectra of 3-methoxy-7- (3-oxocyclohex-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5s
Electronic Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013
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New Journal of Chemistry
Page 59 of 63
55. 1 H NMR Spectra of 1-(5,5-dimethyl-3-oxocyclohex-1-enyl)pyridin-2(1H)-one, 5t
Electronic Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013
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New Journal of Chemistry
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56. 13 C NMR Spectra of 1-(5,5-dimethyl-3-oxocyclohex-1-enyl)pyridin-2(1H)-one, 5t
Electronic Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013
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New Journal of Chemistry
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57. LCMS Spectra of 1-(5,5-dimethyl-3-oxocyclohex-1-enyl)pyridin-2(1H)-one, 5t
Electronic Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013
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New Journal of Chemistry
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58. LCMS Spectra of 1-(3-oxo-5-phenylcyclohex-1-enyl)pyridin-2(1H)-one, 5u
Electronic Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013
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New Journal of Chemistry
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59. LCMS Spectra of 1-(5-(4-chlorophenyl)-3-oxocyclohex-1-enyl)pyridin-2(1H)-one, 5v
Electronic Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013