new journal of chemistry · 2013. 11. 29. · new journal of chemistry page 1 of 63 new journal of...

New Journal of Chemistry

Page 1 of 63


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

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


Page 2 of 63

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



Page 3 of 63

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



Page 4 of 63

59. LCMS Spectra of 1-(5-(4-chlorophenyl)-3-oxocyclohex-1-enyl)pyridin-2(1H)-one, 5v .............................................................. 63



Page 5 of 63

1. 1H NMR spectra of 3-oxocyclopent-1-enyl trifluoromethanesulfonate



Page 6 of 63

2. 13 C NMR Spectra of 3-oxocyclopent-1-enyl trifluoromethanesulfonate



Page 7 of 63

3. 19 F NMR Spectra of 3-oxocyclopent-1-enyl trifluoromethanesulfonate



Page 8 of 63

4. 1H NMR Spectra of 3-oxocyclopent-1-enyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate



Page 9 of 63

5. 13 C NMR Spectra of 3-oxocyclopent-1-enyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate



Page 10 of 63

6. 19 F NMR Spectra of 3-oxocyclopent-1-enyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate



Page 11 of 63

7. 1 H NMR Spectra of 3-oxocyclohex-1-enyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate



Page 12 of 63

8. 13 C NMR Spectra of 3-oxocyclohex-1-enyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate



Page 13 of 63

9. 1 H NMR spectra of 5-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5a



Page 14 of 63

10. 13 C NMR spectra of 5-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5a



Page 15 of 63

11. IR spectra of 5-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5a

Fri Jan 04 15:08:02 2013 (GMT+05:30)

%T

ran

smitt

an

ce

3354.4

3133.7

3096.9

2922954.31

.7

2855.8

2361

2332.8

.4

1707.9

1670.8

1619.8

1574.4

1523.7

1407.6

1371.2

1306.4

1462.0

1437.4

1341.1

1242.7

1184.2

1139.8

1040.2

963.7

870.6

988.9

847.1

819.4

765.2

628.4

4

97.8

562.4

525.0

467.0

403.0

IR Report

100

95

90

85

80

75

70

65

4000 3500 3000 2500 2000 1500 1000 500

Wavenumbers (cm-1)



Page 16 of 63

12. LCMS spectra of 5-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5a



Page 17 of 63

13. 1 H NMR spectra of 4-methyl-3-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5b



Page 18 of 63

14. 13 C NMR spectra of 4-methyl-3-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5b



Page 19 of 63

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



Page 22 of 63

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



Page 24 of 63

20. LCMS Spectra of 1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5c



Page 25 of 63

21. 1 H NMR Spectra of 3-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5d



Page 26 of 63

22. 13 C NMR Spectra of 3-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5d



Page 27 of 63

23. LCMS Spectra of 3-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5d



Page 28 of 63

24. 1 H NMR Spectra of 4-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5e



Page 29 of 63

25. 13 C NMR Spectra of 4-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5e



Page 30 of 63

26. IR Spectra of 4-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5e



Page 31 of 63

27. LCMS Spectra of 4-methyl-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5e



Page 32 of 63

28. 1 H NMR Spectra of 5-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5f



Page 33 of 63

29. 13 CNMR Spectra of 5-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5f



Page 34 of 63

30. IR Spectra of 5-nitro-1-(3-oxocyclopent-1-enyl) pyridin-2 (1 H)-one, 5f



Page 35 of 63

31. 1 H NMR Spectra of 1, 3-bis (3-oxocyclopent-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5i



Page 36 of 63

32. 13 C NMR Spectra of 1, 3-bis (3-oxocyclopent-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5i



Page 37 of 63

33. IR Spectra of 1, 3-bis (3-oxocyclopent-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5i



Page 38 of 63

34. LCMS Spectra of 1, 3-bis (3-oxocyclopent-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5i



Page 39 of 63

35. 1 H NMR Spectra of 3-chloro-7-(3-oxocyclopent-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5k



Page 40 of 63

36. 13 C NMR Spectra of 3-chloro-7-(3-oxocyclopent-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5k



Page 41 of 63

37. IR Spectra of 3-chloro-7-(3-oxocyclopent-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5k



Page 42 of 63

38. LCMS Spectra of 3-chloro-7-(3-oxocyclopent-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5k



Page 43 of 63

39. 1 H NMR Spectra of 1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5m



Page 44 of 63

40. 13 C NMR Spectra of 1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5m



Page 45 of 63

41. IR Spectra of 1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5m



Page 46 of 63

42. LCMS Spectra of 1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5m



Page 47 of 63

43. 1 H NMR Spectra of 5-methyl-1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5o



Page 48 of 63

44. 13 C NMR Spectra of 5-methyl-1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5o



Page 49 of 63

45. LCMS Spectra of 5-methyl-1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5o



Page 50 of 63

46. 1 H NMR Spectra of 4-(trifluoromethyl)-1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5p



Page 51 of 63

47. LCMS Spectra of 4-(trifluoromethyl)-1-(3-oxocyclohex-1-enyl) pyridin-2 (1 H)-one, 5p



Page 52 of 63

48. 1 H NMR Spectra of 1-(3-oxocyclohex-1-enyl)-1 H-benzo[d]imidazol-2 (3 H)-one, 5q



Page 53 of 63

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

Thu Mar 07 15:50:39 2013 (GMT+05:30)

%T

ran

smitt

ance

3051.4

2944.7

2896.0

1704.1

1659.5

1619.3

1595.8

1477.1

1417.9

1345.0

1381.2

1307.7

1286.8

1248.3

1221.5

1157.2

1101.2

1032.7

966.9

931.8

898.8

847.3

808.2

775.6

746.1

727.0

690.5

654.3

604.8

539.6

IR Report

100

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90

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75

70

65

60

55

50

45

40

4000

3500

3000

2500

2000

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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



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



Page 57 of 63

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)



Page 58 of 63

54. LCMS Spectra of 3-methoxy-7- (3-oxocyclohex-1-enyl)-1, 7-naphthyridin-8 (7 H)-one, 5s



Page 59 of 63

55. 1 H NMR Spectra of 1-(5,5-dimethyl-3-oxocyclohex-1-enyl)pyridin-2(1H)-one, 5t



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56. 13 C NMR Spectra of 1-(5,5-dimethyl-3-oxocyclohex-1-enyl)pyridin-2(1H)-one, 5t



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57. LCMS Spectra of 1-(5,5-dimethyl-3-oxocyclohex-1-enyl)pyridin-2(1H)-one, 5t



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58. LCMS Spectra of 1-(3-oxo-5-phenylcyclohex-1-enyl)pyridin-2(1H)-one, 5u



Page 63 of 63

59. LCMS Spectra of 1-(5-(4-chlorophenyl)-3-oxocyclohex-1-enyl)pyridin-2(1H)-one, 5v


new journal of chemistry · 2013. 11. 29. · new journal of chemistry page 1 of 63 new journal of...

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