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2-Methoxyphenylisocyanate: A chemoselective multitasking reagent for amine protection/deprotection sequence
Anand Babu Velappan,a Kogatam Subhashini,a Dhrubajyoti Datta,b Rakshantha Srithar,a Nanjappan Gunasekarana and Joy Debnatha*
aDepartment of Chemistry, SCBT, SASTRA Deemed University, Tamilnadu 613401, India. bDepartment of Chemistry, Indian Institute of Science Education and Research , Pune, Maharashtra,
411008, India.
Supporting Information II
1. 1H-NMR for 2a 4 2. 13C-NMR for 2a 4 3. 1H-NMR for 3a 5 4. 13C-NMR for 3a 5 5. 1H-NMR for 2b 6 6. 13C-NMR for 2b 6 7. 1H-NMR for 3b 7 8. 13C-NMR for 3b 7 9. 1H-NMR for 2c 8 10. 13C-NMR for 2c 8 11. 1H-NMR for 3c 9 12. 13C-NMR for 3c 9 13. 1H-NMR for 2d 10 14. 13C-NMR for 2d 10 15. 1H-NMR for 3d 11 16. 13C-NMR for 3d 11 17. 1H-NMR for 2e 12 18. 13C-NMR for 2e 12 19. 1H-NMR for 3e 13 20. 13C-NMR for 3e 13 21. 1H-NMR for 2f 14 22. 13C-NMR for 2f 14 23. 1H-NMR for 3f 15 24. 13C-NMR for 3f 15 25. 1H-NMR for 2g 16 26. 13C-NMR for 2g 16 27. 1H-NMR for 3g 17 28. 13C-NMR for 3g 17 29. 1H-NMR for 2h 18 30. 13C-NMR for 2h 18 31. 1H-NMR for 3h 19 32. 13C-NMR for 3h 19 33. 1H-NMR for 2i 20 34. 13C-NMR for 2i 20 35. 1H-NMR for 3i 21 36. 13C-NMR for 3i 21 37. 1H-NMR for 2j 22 38. 13C-NMR for 2j 22 39. 1H-NMR for 3j 23 40. 13C-NMR for 3j 23
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.This journal is © the Partner Organisations 2019
2
41. 1H-NMR for 2k 24 42. 13C-NMR for 2k 24 43. 1H-NMR for 3k 25 44. 13C-NMR for 3k 25 45. 1H-NMR for 2l 26 46. 13C-NMR for 2l 26 47. 1H-NMR for 3l 27 48. 1H-NMR for 2m 28 49. 13C-NMR for 2m 28 50. 1H-NMR for 3m 29 51. 13C-NMR for 3m 29 52. 1H-NMR for 2n 30 53. 13C-NMR for 2n 30 54. 1H-NMR for 2o 31 55. 13C-NMR for 2o 31 56. 1H-NMR for 3o 32 57. 13C-NMR for 3o 32 58. 1H-NMR for 2p 33 59. 13C-NMR for 2p 33 60. 1H-NMR for 2q 34 61. 13C-NMR for 2q 34 62. 1H-NMR for 2r 35 63. 13C-NMR for 2r 35 64. 1H-NMR for 3r 36 65. 13C-NMR for 3r 36 66. 1H-NMR for 2s 37 67. 13C-NMR for 2s 37 68. 1H-NMR for 3s 38 69. 13C-NMR for 3s 38 70. 1H-NMR for 2t 39 71. 13C-NMR for 2t 39 72. 1H-NMR for 3t 40 73. 13C-NMR for 3t 40 74. 1H-NMR for 2u 41 75. 13C-NMR for 2u 41 76. 1H-NMR for 3u 42 77. 13C-NMR for 3u 42 78. 1H-NMR for 1-(3-Methoxy-phenyl)-3-o-tolyl-urea (5) 43 79. 13C-NMR for 1-(3-Methoxy-phenyl)-3-o-tolyl-urea (5) 43 80. 1H-NMR for 1-(3-Hydroxy-phenyl)-3-o-tolyl-urea (6) 44 81. 13C-NMR for 1-(3-Hydroxy-phenyl)-3-o-tolyl-urea (6) 44 82. 1H-NMR for 1-(4-Methoxy-phenyl)-3-o-tolyl-urea (7) 45 83. 13C-NMR for 1-(4-Methoxy-phenyl)-3-o-tolyl-urea (7) 45 84. 1H-NMR for 1-(4-Hydroxy-phenyl)-3-o-tolyl-urea (8) 46 85. 13C-NMR for 1-(4-Hydroxy-phenyl)-3-o-tolyl-urea (8) 46 86. 1H-NMR for 3H-Benzooxazol-2-one (4) 47 87. 13C-NMR for 3H-Benzooxazol-2-one (4) 47 88. HRMS for 3H-Benzooxazol-2-one (4) 48 89. 1H-NMR for 9 49 90. 1H-NMR for 10 49 91. 1H-NMR for 11 50 92. 1H-NMR for 12 50 93. 1H-NMR for 13 51 94. 1H-NMR for 1-(4-Amino-phenyl)-3-(2-methoxy-phenyl)-urea 51 95. 1H-NMR for 15 52
3
96. 1H-NMR for 16 52 97. 1H-NMR for 17 53 98. 1H-NMR for 18 53 99. 1H-NMR for 1-(4-Amino-phenyl)-3-(2-hydroxy-phenyl)-urea 54 100. p-phenylenediamine 54 101. 1H-NMR for Boc-aniline 55 102. 1H-NMR for Troc-aniline 55 103. 1H-NMR for Fmoc-aniline 56 104. 1H-NMR for Ac-aniline 56 105. 1H-NMR for Benzyl-aniline 57 106. 1H-NMR for Allyl-aniline 57 107. 1H-NMR for Boc-phenol 58 108. 1H-NMR for Troc- phenol 58 109. 1H-NMR for Ac- phenol 59 110. 1H-NMR for TBS- phenol 59 111. 1H-NMR for Benzyl- phenol 60 112. 1H-NMR for allyl- phenol 60 113. 1H-NMR for 20 61 114. 13C-NMR for 20 61 115. 1H-NMR for 22 62 116. 13C-NMR for 22 62 117. 1H-NMR for 24 63 118. 13C-NMR for 24 63 119. 1H-NMR for 26 64 120. 13C-NMR for 26 64
4
1H-NMR for 2a:
13C-NMR for 2a:
5
1H-NMR for 3a:
13C-NMR for 3a:
6
1H-NMR for 2b:
13C-NMR for 2b:
7
1H-NMR for 3b:
13C-NMR for 3b:
8
1H-NMR for 2c:
13C-NMR for 2c:
9
1H-NMR for 3c:
13C-NMR for 3c:
10
1H-NMR for 2d:
13C-NMR for 2d:
11
1H-NMR for 3d:
13C-NMR for 3d:
12
1H-NMR for 2e:
13C-NMR for 2e:
13
1H-NMR for 3e:
13C-NMR for 3e:
14
1H-NMR for 2f:
13C-NMR for 2f:
15
1H-NMR for 3f:
13C-NMR for 3f:
16
1H-NMR for 2g:
13C-NMR for 2g:
17
1H-NMR for 3g:
13C-NMR for 3g:
18
1H-NMR for 2h:
13C-NMR for 2h:
19
1H-NMR for 3h:
13C-NMR for 3h:
20
1H-NMR for 2i:
13C-NMR for 2i:
21
1H-NMR for 3i:
13C-NMR for 3i:
22
1H-NMR for 2j:
13C-NMR for 2j:
23
1H-NMR for 3j:
13C-NMR for 3j:
24
1H-NMR for 2k:
13C-NMR for 2k:
25
1H-NMR for 3k:
13C-NMR for 3k:
26
1H-NMR for 2l:
13C-NMR for 2l:
27
1H-NMR for 3l:
28
1H-NMR for 2m:
13C-NMR for 2m:
29
1H-NMR for 3m:
13C-NMR for 3m:
30
1H-NMR for 2n:
13C-NMR for 2n:
31
1H-NMR for 2o:
13C-NMR for 2o:
32
1H-NMR for 3o:
13C-NMR for 3o:
33
1H-NMR for 2p:
13C-NMR for 2p:
34
1H-NMR for 2q:
13C-NMR for 2q:
35
1H-NMR for 2r:
13C-NMR for 2r:
36
1H-NMR for 3r:
13C-NMR for 3r:
37
1H-NMR for 2s:
13C-NMR for 2s:
38
1H-NMR for 3s:
13C-NMR for 3s:
39
1H-NMR for 2t:
13C-NMR for 2t:
40
1H-NMR for 3t:
13C-NMR for 3t:
41
1H-NMR for 2u:
13C-NMR for 2u:
42
1H-NMR for 3u:
13C-NMR for 3u:
43
1H-NMR for 1-(3-Methoxy-phenyl)-3-o-tolyl-urea (5):
13C-NMR for 1-(3-Methoxy-phenyl)-3-o-tolyl-urea (5):
44
1H-NMR for 1-(3-Hydroxy-phenyl)-3-o-tolyl-urea (6):
13C-NMR for 1-(3-Hydroxy-phenyl)-3-o-tolyl-urea (6):
45
1H-NMR for 1-(4-Methoxy-phenyl)-3-o-tolyl-urea (7):
13C-NMR for 1-(4-Methoxy-phenyl)-3-o-tolyl-urea (7):
46
1H-NMR for 1-(4-Hydroxy-phenyl)-3-o-tolyl-urea (8):
13C-NMR for 1-(4-Hydroxy-phenyl)-3-o-tolyl-urea (8):
47
1H-NMR for 4:
13C-NMR for 4:
48
HRMS for 4:
49
1H-NMR for 9:
1H-NMR for 10:
50
1H-NMR for 11:
1H-NMR for 12:
51
1H-NMR for 13: 1H-NMR for 1-(4-Amino-phenyl)-3-(2-methoxy-phenyl)-urea:
52
1H-NMR for 15:
1H-NMR for 16:
53
1H-NMR for 17: 1H-NMR for 18:
54
1H-NMR for 1-(4-Amino-phenyl)-3-(2-hydroxy-phenyl)-urea:
p-phenylenediamine:
55
1H-NMR for Boc-aniline:
1H-NMR for Troc-aniline:
56
1H-NMR for Fmoc-aniline:
1H-NMR for Ac-aniline:
57
1H-NMR for Bn-aniline:
1H-NMR for Allyl-aniline:
58
1H-NMR for Boc-phenol:
1H-NMR for Troc-phenol:
59
1H-NMR for Ac-phenol:
1H-NMR for TBS-phenol:
60
1H-NMR for Benzyl-phenol:
1H-NMR for Allyl-phenol:
61
1H-NMR of 20:
13C-NMR of 20:
62
1H-NMR of 22:
13C-NMR of 22:
63
1H-NMR of 24:
13C-NMR of 24:
64
1H-NMR of 26:
13C-NMR of 26:
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