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1 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Supporting Information Regioselective 6-endo-dig Iodocyclization: An accessible approach for Iodo-benzo[a]phenazines Sonu Kumar, a Mohammad Mujahid b and Akhilesh K. Verma a * a Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, University of Delhi, Delhi, , India b Wolfson college, University of Oxford, U.K. S.No Contents Page No. 1 X-ray crystallographic studies S2-S3 2 References S4-S4 9 Copies of 1 H and 13 C NMRs S6-S147 S1
2 X-ray crystallographic studies Figure S1. ORTEP drawing of compound 5e drawn at 50% probability level The structure of 5e was solved by the direct methods using SIR-92 and refined by full-matrix least-squares refinement techniques on F 2 using SHELXL97. 2 The hydrogen atoms were placed into the calculated positions and included in the last cycles of the refinement. All calculations were done using Wingx software package. 3 CCDC numbers of 5e is S2
3 Table 1. Crystal data and structure refinement for 5e Empirical formula C 28 H 25 I N 2 Formula weight Temperature 293(2) K Wavelength Å Crystal system Triclinic Space group P -1 Unit cell dimensions a = (3) Å α = (4) b = (4) Å β = (3) c = (6) Å γ = (3) Volume (9) Å 3 Z 2 Density (calculated) Mg/m 3 Absorption coefficient mm -1 F(000) 520 Crystal size x x mm 3 Theta range for data collection to Index ranges -11 h 11, -14 k 14, -14 l 14 Reflections collected Independent reflections 4098 [R(int) = ] Completeness to theta = % Absorption correction Semi-empirical from equivalents Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 4098 / 0 / 284 Goodness-of-fit on F Final R indices [I>2σ (I)] a,b R 1 = , wr 2 = R indices (all data) R 1 = , wr 2 = Largest diff. peak and hole and e.å -3 a R = ( Fo Fc )/ Fo ; b wr = { [w(f o 2 F c 2 ) 2 ]/ [w(f o 2 ) 2 ]} 1/2 S3
4 References 1. a) SMART: Bruker Molecular Analysis Research Tool, version Bruker Analytical X-ray System, b) SAINT-NT, version 6.45, Bruker Analytical X-Ray System, c) SHELXTL-NT, version 6.10, Bruker Analytical X-ray System, G. M. Sheldrick, Acta Cryst., 2008, A64, L. J. Farrugia, WinGX Version , An integrated system of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-Ray Diffraction Data; Department of Chemistry, University of Glasgow ( ). S4
5 Copies of 1 H and 13 C NMR S5
6 1 H NMR 2-Chloro-3-(phenylethynyl)quinoxaline (1aa) S6
7 13 C{ 1 H} NMR 2-Chloro-3-(phenylethynyl)quinoxaline (1aa) S7
8 1 H NMR 2,3-bis(Phenylethynyl)quinoxaline (1ab) S8
9 13 C{ 1 H} NMR 2,3-bis(Phenylethynyl)quinoxaline (1ab) S9
10 HRMS 2,3-bis(Phenylethynyl)quinoxaline (1ab) S10
11 1 H NMR 2-(p-Tolyl)-3-(m-tolylethynyl)quinoxaline (4b) S11
12 13 C{ 1 H} NMR 2-(p-Tolyl)-3-(m-tolylethynyl)quinoxaline (4b) S12
13 HRMS 2-(p-Tolyl)-3-(m-tolylethynyl)quinoxaline (4b) S13
14 1 H NMR Me N N Me 2-(p-Tolyl)-3-(o-tolylethynyl)quinoxaline (4c) S14
15 13 C{ 1 H} NMR 2-(p-Tolyl)-3-(o-tolylethynyl)quinoxaline (4c) S15
16 HRMS 2-(p-Tolyl)-3-(o-tolylethynyl)quinoxaline (4c) S16
17 1 H NMR 2-((4-Ethylphenyl)ethynyl)-3-(3,4,5-trimethoxyphenyl)quinoxaline (4k) S17
18 13 C{ 1 H} NMR 2-((4-Ethylphenyl)ethynyl)-3-(3,4,5-trimethoxyphenyl)quinoxaline (4k) S18
19 HRMS 2-((4-Ethylphenyl)ethynyl)-3-(3,4,5-trimethoxyphenyl)quinoxaline (4k) S19
20 1 H NMR N C 4 H 9 N 2-(Hex-1-yn-1-yl)-3-phenylquinoxaline (4s) S20
21 13 C{ 1 H} NMR 2-(Hex-1-yn-1-yl)-3-phenylquinoxaline (4s) S21
22 1 H NMR 6-methyl-2-phenyl-3-(thiophen-3-ylethynyl)quinoxaline (6a) S22
23 13 C{ 1 H} NMR 6-methyl-2-phenyl-3-(thiophen-3-ylethynyl)quinoxaline (6a) S23
24 HRMS 6-methyl-2-phenyl-3-(thiophen-3-ylethynyl)quinoxaline (6a) S24
25 1 H NMR 2-(2,5-Dimethoxyphenyl)-3-((4-methoxyphenyl)ethynyl)-6-methylquinoxaline (6c) S25
26 13 C{ 1 H} NMR 2-(2,5-Dimethoxyphenyl)-3-((4-methoxyphenyl)ethynyl)-6-methylquinoxaline (6c) S26
27 HRMS 2-(2,5-Dimethoxyphenyl)-3-((4-methoxyphenyl)ethynyl)-6-methylquinoxaline (6c) S27
28 1 H NMR 3-((4-(tert-Butyl)phenyl)ethynyl)-2-(2,5-dimethoxyphenyl)-6-methylquinoxaline (6d) S28
29 13 C{ 1 H} NMR 3-((4-(tert-Butyl)phenyl)ethynyl)-2-(2,5-dimethoxyphenyl)-6-methylquinoxaline (6d) S29
30 HRMS 3-((4-(tert-Butyl)phenyl)ethynyl)-2-(2,5-dimethoxyphenyl)-6-methylquinoxaline (6d) S30
31 1 H NMR 3-((4-(tert-Butyl)phenyl)ethynyl)-6-methyl-2-(3,4,5-trimethoxyphenyl)quinoxalin e (6e) S31
32 13 C{ 1 H} NMR t Bu Me N N OMe OMe OMe 3-((4-(tert-Butyl)phenyl)ethynyl)-6-methyl-2-(3,4,5-trimethoxyphenyl)quinoxalin e (6e) S32
33 HRMS t Bu Me N N OMe OMe OMe 3-((4-(tert-Butyl)phenyl)ethynyl)-6-methyl-2-(3,4,5-trimethoxyphenyl)quinoxalin e (6e) S33
34 1 H NMR 6-Methyl-3-(thiophen-3-ylethynyl)-2-(3,4,5-trimethoxyphenyl)quinoxaline (6f) S34
35 13 C{ 1 H} NMR 6-Methyl-3-(thiophen-3-ylethynyl)-2-(3,4,5-trimethoxyphenyl)quinoxaline (6f) S35
36 HRMS 6-Methyl-3-(thiophen-3-ylethynyl)-2-(3,4,5-trimethoxyphenyl)quinoxaline (6f) S36
37 1 H NMR Me N N 6-Methyl-3-(phenylethynyl)-2-(thiophen-3-yl)quinoxaline (6g) S S37
38 13 C{ 1 H} NMR Me N N 6-Methyl-3-(phenylethynyl)-2-(thiophen-3-yl)quinoxaline (6g) S S38
39 HRMS 6-Methyl-3-(phenylethynyl)-2-(thiophen-3-yl)quinoxaline (6g) S39
40 1 H NMR 6-Methyl-2-(thiophen-3-yl)-3-(thiophen-3-ylethynyl)quinoxaline (6i) S40
41 13 C{ 1 H} NMR 6-Methyl-2-(thiophen-3-yl)-3-(thiophen-3-ylethynyl)quinoxaline (6i) S41
42 HRMS 6-Methyl-2-(thiophen-3-yl)-3-(thiophen-3-ylethynyl)quinoxaline (6i) S42
43 1 H NMR 6-Iodo-3-methyl-5-(p-tolyl)benzo[a]phenazine (5a) S43
44 13 C{ 1 H} NMR 6-Iodo-3-methyl-5-(p-tolyl)benzo[a]phenazine (5a) S44
45 HRMS 6-Iodo-3-methyl-5-(p-tolyl)benzo[a]phenazine (5a) S45
46 1 H NMR 6-Iodo-3-methyl-5-(m-tolyl)benzo[a]phenazine (5b) S46
47 13 C{ 1 H} NMR 6-Iodo-3-methyl-5-(m-tolyl)benzo[a]phenazine (5b) S47
48 HRMS 6-Iodo-3-methyl-5-(m-tolyl)benzo[a]phenazine (5b) S48
49 1 H NMR 6-Iodo-3-methyl-5-(o-tolyl)benzo[a]phenazine (5c) S49
50 13 C{ 1 H} NMR 6-Iodo-3-methyl-5-(o-tolyl)benzo[a]phenazine (5c) S50
51 HRMS 6-Iodo-3-methyl-5-(o-tolyl)benzo[a]phenazine (5c) S51
52 1 H NMR 6-Iodo-3-methyl-5-(thiophen-3-yl)benzo[a]phenazine (5d) S52
53 13 C{ 1 H} NMR 6-Iodo-3-methyl-5-(thiophen-3-yl)benzo[a]phenazine (5d) S53
54 HRMS 6-Iodo-3-methyl-5-(thiophen-3-yl)benzo[a]phenazine (5d) S54
55 1 H NMR 5-(4-(tert-Butyl)phenyl)-3-ethyl-6-iodobenzo[a]phenazine (5e) S55
56 13 C{ 1 H} NMR 5-(4-(tert-Butyl)phenyl)-3-ethyl-6-iodobenzo[a]phenazine (5e) S56
57 HRMS 5-(4-(tert-Butyl)phenyl)-3-ethyl-6-iodobenzo[a]phenazine (5e) S57
58 1 H NMR 6-Iodo-2,4-dimethoxy-5-(o-tolyl)benzo[a]phenazine (5f) S58
59 13 C{ 1 H} NMR 6-Iodo-2,4-dimethoxy-5-(o-tolyl)benzo[a]phenazine (5f) S59
60 HRMS 6-Iodo-2,4-dimethoxy-5-(o-tolyl)benzo[a]phenazine (5f) S60
61 1 H NMR 5-(4-(tert-Butyl)phenyl)-6-iodo-2,4-dimethoxybenzo[a]phenazine (5g) S61
62 13 C{ 1 H} NMR 5-(4-(tert-Butyl)phenyl)-6-iodo-2,4-dimethoxybenzo[a]phenazine (5g) S62
63 HRMS 5-(4-(tert-Butyl)phenyl)-6-iodo-2,4-dimethoxybenzo[a]phenazine (5g) S63
64 1 H NMR 5-Cyclopropyl-6-iodo-2,4-dimethoxybenzo[a]phenazine (5h) S64
65 13 C{ 1 H} NMR 5-Cyclopropyl-6-iodo-2,4-dimethoxybenzo[a]phenazine (5h) S65
66 HRMS 5-Cyclopropyl-6-iodo-2,4-dimethoxybenzo[a]phenazine (5h) S66
67 1 H NMR I N C 4 H 9 N OMe OMe 5-Butyl-6-iodo-2,4-dimethoxybenzo[a]phenazine (5i) S67
68 13 C{ 1 H} NMR 5-Butyl-6-iodo-2,4-dimethoxybenzo[a]phenazine (5i) S68
69 HRMS 5-Butyl-6-iodo-2,4-dimethoxybenzo[a]phenazine (5i) S69
70 1 H NMR N I N OMe OMe OMe 6-Iodo-2,3,4-trimethoxy-5-phenylbenzo[a]phenazine (5j) S70
71 13 C{ 1 H} NMR 6-Iodo-2,3,4-trimethoxy-5-phenylbenzo[a]phenazine (5j) S71
72 HRMS 6-Iodo-2,3,4-trimethoxy-5-phenylbenzo[a]phenazine (5j) S72
73 1 H NMR 5-(4-Ethylphenyl)-6-iodo-2,3,4-trimethoxybenzo[a]phenazine (5k) S73
74 13 C{ 1 H} NMR 5-(4-Ethylphenyl)-6-iodo-2,3,4-trimethoxybenzo[a]phenazine (5k) S74
75 HRMS 5-(4-Ethylphenyl)-6-iodo-2,3,4-trimethoxybenzo[a]phenazine (5k) S75
76 1 H NMR 6-Iodo-2,3,4-trimethoxy-5-(4-methoxyphenyl)benzo[a]phenazine (5l) S76
77 13 C{ 1 H} NMR 6-Iodo-2,3,4-trimethoxy-5-(4-methoxyphenyl)benzo[a]phenazine (5l) S77
78 HRMS 6-Iodo-2,3,4-trimethoxy-5-(4-methoxyphenyl)benzo[a]phenazine (5l) S78
79 1 H NMR 4-(6-Iodo-2,3,4-trimethoxybenzo[a]phenazin-5-yl)-N,N-dimethylaniline (5m) S79
80 13 C{ 1 H} NMR 4-(6-Iodo-2,3,4-trimethoxybenzo[a]phenazin-5-yl)-N,N-dimethylaniline (5m) S80
81 HRMS 4-(6-Iodo-2,3,4-trimethoxybenzo[a]phenazin-5-yl)-N,N-dimethylaniline (5m) S81
82 1 H NMR 6-Iodo-2,3,4-trimethoxy-5-(o-tolyl)benzo[a]phenazine (5n) S82
83 13 C{ 1 H} NMR 6-Iodo-2,3,4-trimethoxy-5-(o-tolyl)benzo[a]phenazine (5n) S83
84 HRMS 6-Iodo-2,3,4-trimethoxy-5-(o-tolyl)benzo[a]phenazine (5n) S84
85 1 H NMR 5-(2-Fluorophenyl)-6-iodo-2,3,4-trimethoxybenzo[a]phenazine (5o) S85
86 13 C{ 1 H} NMR 5-(2-Fluorophenyl)-6-iodo-2,3,4-trimethoxybenzo[a]phenazine (5o) S86
87 HRMS 5-(2-Fluorophenyl)-6-iodo-2,3,4-trimethoxybenzo[a]phenazine (5o) S87
88 1 H NMR 6-Iodo-2,3,4-trimethoxy-5-(4-(trifluoromethyl)phenyl)benzo[a]phenazine (5p) S88
89 13 C{ 1 H} NMR 6-Iodo-2,3,4-trimethoxy-5-(4-(trifluoromethyl)phenyl)benzo[a]phenazine (5p) S89
90 HRMS 6-Iodo-2,3,4-trimethoxy-5-(4-(trifluoromethyl)phenyl)benzo[a]phenazine (5p) S90
91 1 H NMR 6-Iodo-5-phenylbenzo[a]phenazine (5q) S91
92 13 C{ 1 H} NMR 6-Iodo-5-phenylbenzo[a]phenazine (5q) S92
93 HRMS 6-Iodo-5-phenylbenzo[a]phenazine (5q) S93
94 1 HNMR 4-(6-Iodobenzo[a]phenazin-5-yl)-N,N-dimethylaniline (5r) S94
95 13 C{ 1 H} NMR 4-(6-Iodobenzo[a]phenazin-5-yl)-N,N-dimethylaniline (5r) S95
96 HRMS 4-(6-Iodobenzo[a]phenazin-5-yl)-N,N-dimethylaniline (5r) S96
97 1 H NMR 5-Butyl-6-iodobenzo[a]phenazine (5s) S97
98 13 C{ 1 H} NMR 5-Butyl-6-iodobenzo[a]phenazine (5s) S98
99 HRMS 5-Butyl-6-iodobenzo[a]phenazine (5s) S99
100 1 H NMR 4-(4-(tert-Butyl)phenyl)-5-iodothieno[3,2-a]phenazine (5t) S100
101 13 C{ 1 H} NMR 4-(4-(tert-Butyl)phenyl)-5-iodothieno[3,2-a]phenazine (5t) S101
102 HRMS 4-(4-(tert-Butyl)phenyl)-5-iodothieno[3,2-a]phenazine (5t) S102
103 1 H NMR 4-(2-Fluorophenyl)-5-iodothieno[3,2-a]phenazine (5u) S103
104 13 C{ 1 H} NMR 4-(2-Fluorophenyl)-5-iodothieno[3,2-a]phenazine (5u) S104
105 HRMS 4-(2-Fluorophenyl)-5-iodothieno[3,2-a]phenazine (5u) S105
106 1 HNMR 4-Cyclohexyl-5-iodothieno[3,2-a]phenazine (5v) S106
107 13 C{ 1 H} NMR 4-Cyclohexyl-5-iodothieno[3,2-a]phenazine (5v) S107
108 HRMS 4-Cyclohexyl-5-iodothieno[3,2-a]phenazine (5v) S108
109 1 H NMR 4-Cyclopropyl-5-iodothieno[3,2-a]phenazine (5w) S109
110 13 C{ 1 H} NMR 4-Cyclopropyl-5-iodothieno[3,2-a]phenazine (5w) S110
111 HRMS 4-Cyclopropyl-5-iodothieno[3,2-a]phenazine (5w) S111
112 1 H NMR 6-Bromo-2,3,4-trimethoxy-5-(o-tolyl)benzo[a]phenazine (5x) S112
113 13 C{ 1 H} NMR 6-Bromo-2,3,4-trimethoxy-5-(o-tolyl)benzo[a]phenazine (5x) S113
114 HRMS 6-Bromo-2,3,4-trimethoxy-5-(o-tolyl)benzo[a]phenazine (5x) S114
115 1 H NMR 6-Iodo-9-methyl-5-(thiophen-3-yl)benzo[a]phenazine (7a) S115
116 13 C{ 1 H} NMR 6-Iodo-9-methyl-5-(thiophen-3-yl)benzo[a]phenazine (7a) S116
117 HRMS 6-Iodo-9-methyl-5-(thiophen-3-yl)benzo[a]phenazine (7a) S117
118 1 H NMR 5-Cyclopropyl-6-iodo-9-methylbenzo[a]phenazine (7b) S118
119 13 C{ 1 H} NMR 5-Cyclopropyl-6-iodo-9-methylbenzo[a]phenazine (7b) S119
120 HRMS 5-Cyclopropyl-6-iodo-9-methylbenzo[a]phenazine (7b) S120
121 1 H NMR 6-iodo-1,4-dimethoxy-5-(4-methoxyphenyl)-9-methylbenzo[a]phenazine (7c) S121
122 13 C{ 1 H} NMR 6-iodo-1,4-dimethoxy-5-(4-methoxyphenyl)-9-methylbenzo[a]phenazine (7c) S122
123 HRMS 6-iodo-1,4-dimethoxy-5-(4-methoxyphenyl)-9-methylbenzo[a]phenazine (7c) S123
124 1 H NMR 5-(4-(tert-Butyl)phenyl)-6-iodo-1,4-dimethoxy-9-methylbenzo[a]phenazine (7d) S124
125 13 C{ 1 H} NMR 5-(4-(tert-Butyl)phenyl)-6-iodo-1,4-dimethoxy-9-methylbenzo[a]phenazine (7d) S125
126 HRMS 5-(4-(tert-Butyl)phenyl)-6-iodo-1,4-dimethoxy-9-methylbenzo[a]phenazine (7d) S126
127 1 H NMR 5-(4-(tert-Butyl)phenyl)-6-iodo-2,3,4-trimethoxy-9-methylbenzo[a]phenazine (7e) S127
128 13 C{ 1 H} NMR 5-(4-(tert-Butyl)phenyl)-6-iodo-2,3,4-trimethoxy-9-methylbenzo[a]phenazine (7e) S128
129 HRMS 5-(4-(tert-Butyl)phenyl)-6-iodo-2,3,4-trimethoxy-9-methylbenzo[a]phenazine (7e) S129
130 1 H NMR 6-Iodo-2,3,4-trimethoxy-9-methyl-5-(thiophen-3-yl)benzo[a]phenazine (7f) S130
131 13 C{ 1 H} NMR 6-Iodo-2,3,4-trimethoxy-9-methyl-5-(thiophen-3-yl)benzo[a]phenazine (7f) S131
132 HRMS 6-Iodo-2,3,4-trimethoxy-9-methyl-5-(thiophen-3-yl)benzo[a]phenazine (7f) S132
133 1 H NMR 5-Iodo-8-methyl-4-phenylthieno[3,2-a]phenazine (7g) S133
134 13 C{ 1 H} NMR 5-Iodo-8-methyl-4-phenylthieno[3,2-a]phenazine (7g) S134
135 HRMS 5-Iodo-8-methyl-4-phenylthieno[3,2-a]phenazine (7g) S135
136 1 H NMR 5-Iodo-8-methyl-4-(p-tolyl)thieno[3,2-a]phenazine (7h) S136
137 13 C{ 1 H} NMR 5-Iodo-8-methyl-4-(p-tolyl)thieno[3,2-a]phenazine (7h) S137
138 HRMS 5-Iodo-8-methyl-4-(p-tolyl)thieno[3,2-a]phenazine (7h) S138
139 1 H NMR 5-Iodo-8-methyl-4-(thiophen-3-yl)thieno[3,2-a]phenazine (7i) S139
140 13 C{ 1 H} NMR 5-Iodo-8-methyl-4-(thiophen-3-yl)thieno[3,2-a]phenazine (7i) S140
141 HRMS 5-Iodo-8-methyl-4-(thiophen-3-yl)thieno[3,2-a]phenazine (7i) S141
142 1 HNMR 6-((4-Methoxyphenyl)ethynyl)-5-phenylbenzo[a]phenazine (10) S142
143 13 C{ 1 H} NMR 6-((4-Methoxyphenyl)ethynyl)-5-phenylbenzo[a]phenazine (10) S143
144 HRMS 6-((4-Methoxyphenyl)ethynyl)-5-phenylbenzo[a]phenazine (10) S144
145 1 H NMR 5-Phenyl-6-(3,4,5-trimethoxyphenyl)benzo[a]phenazine (11) S145
146 13 C{ 1 H} NMR 5-Phenyl-6-(3,4,5-trimethoxyphenyl)benzo[a]phenazine (11) S146
147 HRMS 5-Phenyl-6-(3,4,5-trimethoxyphenyl)benzo[a]phenazine (11) S147
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