Supplementary Material. Synthesis of novel C-2 substituted imidazoline derivatives having the norbornene/dibenzobarrelene skeletons
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1 Supplementary Material Synthesis of novel C-2 substituted imidazoline derivatives having the norbornene/dibenzobarrelene skeletons İrfan Çapan a and Süleyman Servi b a Gazi University, Technical Sciences Vocational College, Department of Polymer Technology, Ankara, Turkey *b Fırat University, Faculty of Science, Department of Chemistry, Elazığ, Turkey sservi@firat.edu.tr Table of Contents The synthesis of Bicyclo [2.2.1] hepta-5-ene-2,3-dicarbonitrile (1)... S2 The synthesis of 9,10-Dihydro-9,10-ethanoanthracene-11,12-dicarbonitrile (2)... S2 The synthesis of Bicyclo [2.2.1] hept-5-ene-2,3 dicarboxylic acid (13)... S2 General synthesis of C-2 aromatic-heteroaromatic substituted imidazolines S3 Spectra of Compound 3... S4 Spectra of Compound 4... S6 Spectra of Compound 5... S8 Spectra of Compound 6... S10 Spectra of Compound 7... S12 Spectra of Compound 8... S14 Spectra of Compound 9... S16 Spectra of Compound S18 Spectra of Compound S20 Spectra of Compound S23 Spectra of Compound S26 Spectra of Compound S29 Spectra of Compound S32 Spectra of Compound S35 Spectra of Compound S38 Spectra of Compound S41 Spectra of Compound S43 Spectra of Compound S46 Spectra of Compound S49 Spectra of Compound S52 Page S1
2 The synthesis of Bicyclo [2.2.1] hepta-5-ene-2,3-dicarbonitrile (1) The dicyclopentadiene was converted into cyclopentadiene by heating in an oil bath at 180 C. 240 mmol cyclopentadiene (15.86 g) was dissolved in methanol (100 ml) and the solution was cooled to 0 C. To this solution, 120 mmol fumaronitrile (9.37 g) was added and stirred at 0 o C for 1 hour. After stirring for 24 hours at 25 o C, the solvent was removed under reduced pressure. The resulting solid was crystallized with ethanol. 24 Colorless powder; yield: g, 118 mmol (99%); mp: o C, (Ref [24]: o C) g. IR (KBr) (νmax, cm 1 ): 3073, 2999, 2960, 2886, 2241, 1461, 1332, 729; 1 H NMR (400 MHz, CDCl3): δh = 6.39 (2H, s), 3.46 (2H, d, J = 12.8 Hz), 3.19 (1H, m), 2.52 (1H, m), 1.79 (1H, dd, A part of AB system, J = 2.0 Hz), 1.96 (1H, dd, B part of AB system, J = 5.9, 3.4 Hz); 13 C NMR (100 MHz, CDCl3): δc = 137.7, (=CH), 119.9, (CN), 48.4, 46.3 (CH), 47.3 (CH2), 34.8, 34.6 (CH); Anal. calc. for C9H8N2 (144,18): C, 74.98; H, 5.59; N, 19.43; found C, 75.04; H, 5.73; N, %. The synthesis of 9,10-Dihydro-9,10-ethanoanthracene-11,12-dicarbonitrile (2) The mixture of anthracene (1.00 g, 5.61 mmol) and of fumaronitrile (0.44 g, 5.61 mmol) in benzene (30 ml) was refluxed for 24 hours. After the removal of the solvent in vacuo, the residue was crystallized from benzene. 26 Colorless powder; yield: 1.29 g, 5.03 mmol (90%); mp: o C {Ref [24]: 259 o C}; IR (KBr) (νmax, cm 1 ): 3082, 3046, 3026, 2943, 2241, 1460, 1201, 1171, 760, 747; 1 H NMR (400 MHz, CDCl3): δh = (2H, dd, J = 6.4, 2.2 Hz), (2H, m), (4H, m), 4.69 (2H, s), 3.18 (2H, s); 13 C NMR (100 MHz, CDCl3): δc = 139.3, (Ar-Cipso), 128.0, 127.9, 125.8, (Ar. CH), (CN), 46.4 (CHbridgehead), 35.5 (CH); Anal. calc. for C18H12N2 (256,31): C, 84.35; H, 4.72; N, 10.93; found C, 84.52; H, 4.87; N, %. The synthesis of Bicyclo [2.2.1] hept-5-ene-2,3 dicarboxylic acid (13) This compound was prepared according a reported procedure mmol cyclopentadiene, which was obtained by cleavage of dicyclopentadiene at 180 C, and 12.6 mmol fumaric acid were dissolved in the mixture of acetone-water (50 ml, 10 :1) and stirred at 50 C for 24 hours. The solvent was removed under reduced pressure. The resulting solid was crystallized from the mixture of acetone-water (10: 1). Compound 13 was obtained with quantitative yields as colorless powder 2.30 grams. Its melting point corresponds well with the reported one. Colorless powder; yield: 2.30 g, mmol (100%); mp: 174 o C {Ref [25]: o C}; IR (KBr) (νmax, cm 1 ): 3078, 2997, 2984, 2876, 1682, 1422, 1275, 1216, 925, 729, 687; 1 H NMR (400 MHz, CDCl3): δh = (2H, s), 6.30 (1H, dd, J = 5.6, 3.1 Hz), 6.07 (1H, dd, J = 5.6, 2.5 Hz), (2H, m), 3.04 (1H, s), 2.43 (1H, dd, J = 4.1, 1.3 Hz), 1.51 (1H, d, A part of AB system, J = 8.5 Hz), 1.34 (1H, dd, B part of AB system, J = 8.5, 1.5 Hz). 13 C NMR (100 MHz, CDCl3): δc = 175.8, (C=O), 138.0, (C=C), 47.5 (CH2), 47.9, 47.4 (CH), 47.2, 45.4 (CHbridgehead); Anal. calc. for C9H10O4 (182,18): C, 59.34; H, 5.53; found C, 59.56; H, 5.70 %. Page S2
3 General synthesis of C-2 aromatic-heteroaromatic substituted imidazolines 6-10 To a solution of the requisite aldehyde (0.87 mmol) in CH2Cl2 (30 ml), ethylenediamine (1.05 mmol) was added and stirred at 0 C in an argon atmosphere for 2 hours. N-bromosuccinimide (NBS, 1.05 mmol) was slowly added to the mixture. After stirring at room temperature overnight, % NaOH solution was added until ph The mixture was extracted with CH2Cl2. The organic phase was dried with Na2SO4 and the solvent was removed under reduced pressure. The crude products were crystallized from methanol-ethyl acetate 1:1 solvent mixture. 2-Phenyl-4,5-dihydro-1H-imidazole (6) Yield 96% (1.32 g, 9.03 mmol), m.p.: o C, [Ref. 35: o C]; IR (ATR) (νmax, cm 1 ): 3197, 3064, 2970, 2929, 2868, 1636, 1610, 1598, 1573, 1508, 1468, 1269, H NMR (400 MHz, CDCl3) δh: (2H, m), (3H, m), 4.82 (1H, br), 3.77 (4H, s). 13 C NMR (100 MHz, CDCl3) δc: (C=N), 130.7, 128.5, (CHAr), (CAr-ipso), 50.3 (CH2). Anal. calc. for C9H10N2 (146,19): C, 73.94; H, 6.89; N, 19.16; found C, 74.06; H, 7.11; N, (3-Chlorophenyl)-4,5-dihydro-1H-imidazole (7) Yield 94% (1.26 g, 6.98 mmol), m. p.: o C, [Ref. 35: o C]; IR (KBr) (νmax, cm 1 ): 3145, 3075, 2964, 2924, 2857, 1608, 1597, 1563, 1271, H NMR (400 MHz, CDCl3) δh: 7.86 (1H, d, J = 1.2), 7.81 (1H, dd, J = 7.6, 1.2), (1H, m), 7.08 (1H, br), 3.63 (4H, s). 13 C NMR (100 MHz, CDCl3) δc: (C=N), 133.5, (CAr-ipso), 130.7, 130.5, 127.3, (CHAr), 50.2 (CH2). Anal. calc. for C9H9ClN2 (180,64): C, 59.84; H, 5.02; Cl, 19.63; N, 15.51; found C, 59.75; H, 5.26; N, (4-Methoxyphenyl)-4,5-dihydro-1H-imidazole (8) Yields 90% (1.16 g, 6.58 mmol), m. p.: o C, [Ref. 35: o C]; IR (KBr) (νmax, cm 1 ): 3111, 3011, 2929, 2870, 2835, 1602, 1523, 1491, 1252, 1172, 1032, H NMR (400 MHz, CDCl3) δh: (2H, m), (2H, m), 4.91 (1H, br), (3H, d, J = 5.2), 3.73 (4H, s). 13 C NMR (100 MHz, CDCl3) δc: (C=N), 161.4, (CAr-ipso), 128.5, (CHAr), 55.3 (CH3). Anal. calc. for C10H12N2O (176,22): C, 68.16; H, 6.86; N, 15.90; found C, 68.41; H, 7.13; N, (Thiophen-2-yl)-4,5-dihydro-1H-imidazole (9) Yield 92% (1,24 g, 8.15 mmol), m. p.: o C, [Ref. 35: o C]; IR (ATR) (νmax, cm 1 ): 3146, 3084, 2931, 2856, 1596, 1529, 1495, 1101, H NMR (400 MHz, DMSO-d6) δh: (1H, d, J = 4 Hz), (1H, d, J = 4 Hz), (1H, dd, J = 4, 0.8 Hz), 6.99 (1H, br), 3.58 (4H, s). 13 C NMR (100 MHz, DMSO-d6) δc: (C=N), (CAr-ipso), 129.4, 128.3, (CHAr), 60.9 (CH2). Anal. calc. for C7H8N2S (152,22): C, 55.24; H, 5.30; N, 18.40; S, 21.06; found C, 55.52; H, 5.63; N, 18.56; S, Page S3
4 Spectra of Compound 3 FT-IR Spectrum of Compound 3 1 H- 1 H-NMR Spectrum of Compound 3 Page S4
5 13 CAPT-NMR Spectrum of Compound 3 Page S5
6 Spectra of Compound 4 FT-IR Spectrum of Compound 4 1 H- 1 H-NMR Spectrum of Compound 4 Page S6
7 13 CAPT-NMR Spectrum of Compound 4 Page S7
8 Spectra of Compound 5 FT-IR Spectrum of Compound 5 1 H- 1 H-NMR Spectrum of Compound 5 Page S8
9 13 CAPT-NMR Spectrum of Compound 5 Page S9
10 Spectra of Compound 6 FT-IR Spectrum of Compound 6 1 H-NMR Spectrum of Compound 6 Page S10
11 13 CAPT-NMR Spectrum of Compound 6 Page S11
12 Spectra of Compound 7 FT-IR Spectrum of Compound 7 1 H-NMR Spectrum of Compound 7 Page S12
13 13 CAPT-NMR Spectrum of Compound 7 Page S13
14 Spectra of Compound 8 FT-IR Spectrum of Compound 8 1 H-NMR Spectrum of Compound 8 Page S14
15 13 CAPT-NMR Spectrum of Compound 8 Page S15
16 Spectra of Compound 9 FT-IR Spectrum of Compound 9 1 H-NMR Spectrum of Compound 9 Page S16
17 13 CAPT-NMR Spectrum of Compound 9 Page S17
18 Spectra of Compound 10 FT-IR Spectrum of Compound 10 1 H-NMR Spectrum of Compound 10 Page S18
19 13 CAPT-NMR Spectrum of Compound 10 X-ray ORTEP diagram of Compound 10 Page S19
20 Spectra of Compound 15 FT-IR Spectrum of Compound 15 Page S20
21 1 H-NMR Spectrum of Compound CAPT-NMR Spectrum of Compound 15 Page S21
22 HETCOR-NMR Spectrum of Compound 15 Page S22
23 Spectra of Compound 16 FT-IR Spectrum of Compound 16 Page S23
24 1 H-NMR Spectrum of Compound 16 Page S24
25 13 CAPT-NMR Spectrum of Compound 16 HETCOR-NMR Spectrum of Compound 16 Page S25
26 Spectra of Compound 19 FT-IR Spectrum of Compound 19 Page S26
27 1 H-NMR Spectrum of Compound 19 13CAPT-NMR Spectrum of Compound 19 Page S27
28 HETCOR-NMR Spectrum of Compound 19 Page S28
29 Spectra of Compound 20 FT-IR Spectrum of Compound 20 Page S29
30 1 H-NMR Spectrum of Compound 20 Page S30
31 13 CAPT-NMR Spectrum of Compound 20 HETCOR-NMR Spectrum of Compound 20 Page S31
32 Spectra of Compound 21 FT-IR Spectrum of Compound 21 Page S32
33 1 H-NMR Spectrum of Compound CAPT-NMR Spectrum of Compound 21 Page S33
34 HETCOR-NMR Spectrum of Compound 21 Page S34
35 Spectra of Compound 22 FT-IR Spectrum of Compound 22 Page S35
36 1 H-NMR Spectrum of Compound 22 13CAPT-NMR Spectrum of Compound 22 Page S36
37 HETCOR-NMR Spectrum of Compound 22 Page S37
38 %T 9 2 6, 7 4 c m , 0 3 c m - 1 General Papers Spectra of Compound ,8 2894,5 2968,5 3209,49cm ,94cm-1 884,62cm-1 975,83cm-1 910,32cm ,50cm ,26cm ,17cm ,34cm ,36cm ,00cm ,79cm-1 754,58cm-1 637,56cm , 5 1 c m ,16cm-1 488,59cm-1 765,29cm-1 607,87cm-1 540,41cm ,98cm ,68cm ,47cm ,87cm ,68cm FT-IR Spectrum of Compound 23 Page S38
39 1 H-NMR Spectrum of Compound 23 Page S39
40 13 CAPT-NMR Spectrum of Compound 23 HETCOR-NMR Spectrum of Compound 23 Page S40
41 Spectra of Compound 24 FT-IR Spectrum of Compound 24 1 H-NMR Spectrum of Compound 24 Page S41
42 13 CAPT-NMR Spectrum of Compound 24 HETCOR-NMR Spectrum of Compound 24 Page S42
43 Spectra of Compound 28 FT-IR Spectrum of Compound 28 Page S43
44 1 H-NMR Spectrum of Compound CAPT-Spectrum of Compound 28 Page S44
45 HETCOR-NMR Spectrum of Compound 28 Page S45
46 Spectra of Compound 29 FT-IR Spectrum of Compound 29 Page S46
47 1 H-NMR Spectrum of Compound 29 Page S47
48 13 CAPT-NMR Spectrum of Compound 29 HETCOR-NMR Spectrum of Compound 29 Page S48
49 Spectra of Compound 30 FT-IR Spectrum of Compound 30 Page S49
50 1 H-NMR Spectrum of Compound CAPT-NMR Spectrum of Compound 30 Page S50
51 HETCOR-NMR Spectrum of Compound 30 Page S51
52 Spectra of Compound 31 FT-IR Spectrum of Compound 31 1 H-NMR Spectrum of Compound 31 Page S52
53 13 CAPT-NMR Spectrum of Compound 31 HETCOR-NMR Spectrum of Compound 31 Page S53
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