Iodine-catalyzed synthesis of sulfur-bridged enaminones and chromones via double C(sp 2 )-H thiolation
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- Ζεφύρα Λιάπης
- 6 χρόνια πριν
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1 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Iodine-catalyzed synthesis of sulfur-bridged enaminones and chromones via double C(sp 2 )-H thiolation Yong Gao, a Li Wei, a Yunyun Liu a, * and Jie-Ping Wan a, * Contents General experimental information...s1 Characterization data of all products....s2-s11 References..S12 1H and 13C NMR spectra of all products..s13-s38 General experimental information All experiments were carried out under air atmosphere. The enaminones 1 were synthesized following literature process, 1-2 other chemicals and solvents used in the experiments were obtained from commercial sources and used directly without further treatment. 1 H and 13 C NMR spectra were recorded in 400 MHz apparatus in CDCl 3. The frequencies for 1 H NMR and 13 C NMR test are 400 MHz and 100 MHz, respectively. The chemical shifts were reported in ppm with TMS as internal standard. Melting points were tested in X-4A instrument without correcting temperature and the HRMS data for all new products were obtained under ESI model with TOF analyzer. S1
2 Characterization data of all products (2E,2'E)-2,2'-Thiobis(1-phenyl-3-(p-tolylamino)prop-2-en-1-one) (4a). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 13.6 Hz, 2 H), 8.03 (d, J = 13.7 Hz, 2 H), (m, 4 H), (m, 6 H), (m, 8 H), 2.30 (s, 6 H); 13 C NMR (100 MHz, CDCl 3 ): 195.1, 153.2, 140.0, 137.5, 133.9, 130.6, 130.2, 128.6, 128.4, 116.8, 107.4, 20.8; ESI-HRMS Calcd for C 32 H 29 N 2 O 2 S [M + H] , found O O S HN NH (2E,2'E)-2,2'-Thiobis(1-(p-tolyl)-3-(p-tolylamino)prop-2-en-1-one) (4b). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 13.6 Hz, 2 H), 8.05 (d, J = 13.6 Hz, 2 H), 7.50 (d, J = 7.8 Hz, 4 H), (m, 4 H), (m, 8 H), 2.42 (s, 6 H), 2.30 (s, 6 H); 13 C NMR (100 MHz, CDCl 3 ): 195.1, 152.8, 141.0, 137.7, 137.1, 133.7, 130.2, 129.0, 128.9, 116.8, 107.4, 21.5, 20.8; ESI-HRMS Calcd for C 34 H 33 N 2 O 2 S [M + H] , found (2E,2'E)-2,2'-Thiobis(1-(3-methoxyphenyl)-3-(p-tolylamino)prop-2-en-1-one) (4c). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 13.7 Hz, 2 S2
3 H), 8.07 (d, J = 13.7 Hz, 2 H), 7.36 (t, J = 7.9 Hz, 2 H), (m, 14 H), 3.83 (s, 6 H), 2.30 (s, 6 H); 13 C NMR (100 MHz, CDCl 3 ): 194.8, 159.6, 153.3, 141.4, 137.5, 134.0, 130.2, 129.3, 121.0, 116.8, 116.6, 113.6, 107.3, 55.4, 20.8; IR (KBr, cm -1 ) 3141, 3026, 2925, 2858, 1629, 1520, 1464, 1349, 1269, 1120, 1042, 813, 792; ESI-HRMS Calcd for C 34 H 33 N 2 O 4 S [M + H] , found (2E,2'E)-2,2'-Thiobis(1-(o-tolyl)-3-(p-tolylamino)prop-2-en-1-one) (4d). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 13.3 Hz, 2 H), 7.81 (d, J = 13.7 Hz, 2 H), (m, 8 H), (m, 8 H), 2.27 (s, 6 H), 2.18 (s, 6 H); 13 C NMR (100 MHz, CDCl 3 ): 196.2, 153.6, 139.9, 137.2, 135.3, 134.2, 130.7, 130.2, 129.2, 127.0, 125.5, 116.9, 109.3, 20.8, 19.2; ESI-HRMS Calcd for C 34 H 33 N 2 O 2 S [M + H] , found O O S Cl HN NH Cl (2E,2'E)-2,2'-Thiobis(1-(4-chlorophenyl)-3-(p-tolylamino)prop-2-en-1-one) (4e). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 13.6 Hz, 2 H), 7.98 (d, J = 13.7 Hz, 2 H), (m, 8 H), (m, 8 H), 2.32 (s, 6 H); 13 C NMR (100 MHz, CDCl 3 ): 193.7, 153.0, 138.3, 137.3, 136.9, 134.3, 130.3, 130.0, 128.7, 116.8, 107.2, 20.8; ESI-HRMS Calcd for C 32 H 27 Cl 2 N 2 O 2 S [M + H] , found S3
4 MeO O S O OMe MeO HN NH OMe (2E,2'E)-2,2'-Thiobis(1-(3,4-dimethoxyphenyl)-3-(p-tolylamino)prop-2-en-1-one) (4f). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 13.6 Hz, 2 H), 8.09 (d, J = 13.6 Hz, 2 H), (m, 12 H), 6.92 (d, J = 8.2 Hz, 2 H), 3.96 (s, 6 H), 3.91 (s, 6 H), 2.31 (s, 6 H); 13 C NMR (100 MHz, CDCl 3 ): 194.4, 152.2, 151.5, 148.9, 137.8, 133.6, 132.5, 130.2, 122.6, 116.6, 112.0, 110.3, 107.0, 56.0, 20.8; IR (KBr, cm -1 ) 3016, 2931, 2853, 2360, 1643, 1576, 1459, 1336, 1269, 1131, 1019, 864, 797; ESI-HRMS Calcd for C 36 H 37 N 2 O 6 S [M + H] , found O O Cl S Cl Cl HN NH Cl (2E,2'E)-2,2'-Thiobis(1-(3,4-dichlorophenyl)-3-(p-tolylamino)prop-2-en-1-one) (4g). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 13.2 Hz, 2 H), (m, 2 H), 7.67 (s, 2 H), (m, 2 H), 7.39 (d, J = 8.1 Hz, 2 H), 7.25 (d, J = 2.5 Hz, 1 H), (m, 7 H), 2.32 (s, 6 H); 13 C NMR (100 MHz, CDCl 3 ): 192.1, 153.1, 139.7, 137.1, 135.0, 134.6, 133.1, 130.6, 130.4, 127.7, 116.9, 106.9, 20.8; ESI-HRMS Calcd for C 32 H 25 Cl 4 N 2 O 2 S [M + H] , found (2E,2'E)-2,2'-Thiobis(1-(naphthalen-2-yl)-3-(p-tolylamino)prop-2-en-1-one) (4h). S4
5 Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 13.7 Hz, 2 H), (m, 4 H), 7.92 (t, J = 6.8 Hz, 6 H), 7.71 (d, J = 9.7 Hz, 2 H), (m, 4 H), 7.09 (s, 8 H), 2.29 (s, 6 H); 13 C NMR (100 MHz, CDCl 3 ): 195.1, 153.2, 137.5, 137.3, 134.4, 133.9, 132.6, 130.2, 128.8, 128.3, 127.8, 127.4, 126.8, 125.8, 116.8, 107.6, 20.8; ESI-HRMS Calcd for C 40 H 33 N 2 O 2 S [M + H] , found (2E,2'E)-2,2'-Thiobis(1-(thiophen-2-yl)-3-(p-tolylamino)prop-2-en-1-one) (4i). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 13.6 Hz, 2 H), 8.39 (d, J = 13.6 Hz, 2 H), (m, 4 H), (m, 10 H), 2.31 (s, 6 H); 13 C NMR (100 MHz, CDCl 3 ): 185.8, 151.1, 143.5, 137.7, 133.8, 131.1, 131.0, 130.2, 127.4, 116.9, 106.6, 20.8; ESI-HRMS Calcd for C 28 H 25 N 2 O 2 S 3 [M + H] , found (2E,2'E)-2,2'-Thiobis(5-methyl-1-(p-tolylamino)hex-1-en-3-one) (4j). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 12.8 Hz, 2 H), 7.89 (d, J = 13.0 Hz, 2 H), (m, 8 H), 2.75 (d, J = 6.9 Hz, 4 H), 2.33 (s, 6 H), (m, 2 H), 0.98 (d, J = 6.6 Hz, 12 H); 13 C NMR (100 MHz, CDCl 3 ): 202.5, 152.7, 136.6, 135.0, 130.4, 117.3, 102.1, 49.1, 25.4, 22.8, 20.8; IR (KBr, cm -1 ) 3037, 2963, 2925, 2864, 1869, 1613, 1571, 1469, 1349, 1291, 1160, 1056, 808; ESI-HRMS Calcd for C 28 H 37 N 2 O 2 S [M + H] , found S5
6 (2E,2'E)-2,2'-Thiobis(1-phenyl-3-(phenylamino)prop-2-en-1-one) (4k). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 13.2 Hz, 2 H), 8.07 (d, J = 13.6 Hz, 2 H), (m, 14 H), (m, 6 H); 13 C NMR (100 MHz, CDCl 3 ): 195.3, 153.1, 139.9, 139.9, 130.8, 129.7, 128.7, 128.4, 124.2, 116.8, 107.9; IR (KBr, cm -1 ) 3021, 1629, 1581, 1482, 1349, 1272, 1117, 1024, 874, 789; ESI-HRMS Calcd for C 30 H 25 N 2 O 2 S [M + H] , found (2E,2'E)-2,2'-Thiobis(1-phenyl-3-(o-tolylamino)prop-2-en-1-one) (4l). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 13.3 Hz, 2 H), 7.99 (d, J = 13.4 Hz, 2 H), (m, 10 H), 7.22 (d, J = 7.3 Hz, 2 H), (m, 4 H), 6.85 (d, J = 7.8 Hz, 2 H), 2.65 (s, 6 H); 13 C NMR (100 MHz, CDCl 3 ): 194.9, 155.8, 140.3, 139.0, 131.5, 130.4, 129.5, 128.5, 128.3, 126.9, 124.8, 118.0, 107.7, 18.2; ESI-HRMS Calcd for C 32 H 29 N 2 O 2 S [M + H] , found O S O HN NH MeO OMe (2E,2'E)-2,2'-Thiobis(3-((3-methoxyphenyl)amino)-1-phenylprop-2-en-1-one) (4m). Brown solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 13.5 Hz, 2 H), 8.03 (d, J = 13.5 Hz, 2 H), (m, 10 H), 7.22 (t, J = 8.1 Hz, 2 H), S6
7 (m, 4 H), 6.63 (d, J = 8.2 Hz, 2 H), 3.80 (s, 6 H); 13 C NMR (100 MHz, CDCl 3 ): 195.3, 160.8, 153.0, 141.2, 139.8, 130.9, 130.5, 128.7, 128.4, 109.4, 109.3, 108.0, 103.1, 55.4; ESI-HRMS Calcd for C 32 H 29 N 2 O 4 S [M + H] , found (2E,2'E)-2,2'-Thiobis(3-((3-chlorophenyl)amino)-1-phenylprop-2-en-1-one) (4n). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 13.3 Hz, 2 H), 8.00 (d, J = 13.3 Hz, 2 H), (m, 10 H), (m, 2 H), (m, 6 H); 13 C NMR (100 MHz, CDCl 3 ): 195.5, 152.6, 141.2, 139.4, 135.5, 131.2, 130.8, 128.8, 128.5, 124.1, 116.8, 115.2, 108.8; ESI-HRMS Calcd for C 30 H 23 Cl 2 N 2 O 2 S [M + H] , found (2E,2'E)-2,2'-Thiobis(3-((3-nitrophenyl)amino)-1-phenylprop-2-en-1-one) (4o). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 11.3 Hz, 2 H), (m, 6 H), (m, 10 H), 7.37 (d, J = 8.0 Hz, 2 H), 6.16 (d, J = 8.0 Hz, 2 H); 13 C NMR (100 MHz, CDCl 3 ): 191.8, 149.4, 143.4, 141.7, 138.6, 132.1, 130.6, 128.6, 127.5, 122.2, 117.8, 110.0, 95.7; ESI-HRMS Calcd for C 30 H 23 N 4 O 6 S [M + H] , found S7
8 (2E,2'E)-2,2'-Thiobis(3-((4-bromophenyl)amino)-1-phenylprop-2-en-1-one) (4p). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 13.5 Hz, 2 H), 7.99 (d, J = 13.4 Hz, 2 H), (m, 14 H), 7.05 (d, J = 8.5 Hz, 4 H); 13 C NMR (100 MHz, CDCl 3 ): 195.5, 152.7, 139.5, 139.0, 132.7, 131.1, 128.7, 128.5, 118.3, 116.8, 108.5; ESI-HRMS Calcd for C 30 H 23 Br 2 N 2 O 2 S [M + H] , found (2E,2'E)-2,2'-Thiobis(3-((4-fluorophenyl)amino)-1-phenylprop-2-en-1-one) (4q). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 13.5 Hz, 2 H), 7.98 (d, J = 13.5 Hz, 2 H), (m, 10 H), (m, 4 H), 7.02 (t, J = 8.6 Hz, 4 H); 13 C NMR (100 MHz, CDCl 3 ): 195.3, 160.8, 158.4, 153.4, 139.7, 136.2, 130.9, 128.6, 128.5, 118.3, 118.2, 116.6, 116.4, 107.9; IR (KBr, cm -1 ) 3067, 2976, 2861, 1642, 1600, 1469, 1352, 1272, 1117, 1029, 880, 720; ESI-HRMS Calcd for C 32 H 23 F 2 N 2 O 2 S [M + H] , found S8
9 (2E,2'E)-2,2'-Thiobis(3-((4-iodophenyl)amino)-1-phenylprop-2-en-1-one) (4r). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 13.3 Hz, 2 H), 7.99 (d, J = 13.4 Hz, 2 H), (m, 14 H), 6.94 (d, J = 8.6 Hz, 4 H ); 13 C NMR (100 MHz, CDCl 3 ): 195.5, 152.5, 139.7, 139.5, 138.6, 131.1, 128.7, 128.5, 118.7, 108.6, 87.1; ESI-HRMS Calcd for C 30 H 23 I 2 N 2 O 2 S [M + H] , found Diethyl 4,4'-(((1E,1'E)-thiobis(3-oxo-3-phenylprop-1-ene-2,1-diyl))bis(azanediyl)) dibenzoate (4s). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 13.3 Hz, 2 H), 8.10 (d, J = 13.3 Hz, 2 H), 8.01 (d, J = 8.7 Hz, 4 H), (m, 10 H), 7.20 (d, J = 8.8 Hz, 4 H), 4.35 (q, J = 7.1 Hz, 4 H), 1.38 (t, J = 7.1 Hz, 6 H); 13 C NMR (100 MHz, CDCl 3 ): 195.7, 165.9, 152.1, 143.6, 139.3, 131.5, 131.3, 128.8, 128.6, 125.9, 116.0, 109.5, 60.9, 14.3; ESI-HRMS Calcd for C 36 H 33 N 2 O 6 S [M + H] , found (2E,2'E)-2,2'-Thiobis(3-((2,4-dimethylphenyl)amino)-1-phenylprop-2-en-1-one) (4t). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 13.3 Hz, 2 H), 7.93 (d, J = 13.4 Hz, 2 H), (m, 10 H), 7.02 (s, 2 H), 6.91 (d, J = 7.8 Hz, 2 H), 6.75 (d, J = 8.0 Hz, 2 H), 2.59 (s, 6 H), 2.27 (s, 6 H); 13 C NMR (100 MHz, CDCl 3 ): 194.8, 156.2, 140.4, 136.8, 134.7, 132.1, 130.3, 129.6, 128.5, 128.3, 127.4, 118.5, 107.2, 20.7, 18.1; IR (KBr, cm -1 ) 3123, 3037, 2957, 2856, 2360, 1619, S9
10 1592, 1461, 1384, 1269, 1112, 1024, 861, 723; ESI-HRMS Calcd for C 34 H 33 N 2 O 2 S [M + H] , found (2E,2'E)-2,2'-Thiobis(3-((4-methylpyridin-2-yl)amino)-1-phenylprop-2-en-1-one) (4u). Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (d, J = 12.6 Hz, 2 H), 8.83 (d, J = 12.7 Hz, 2 H), 8.02 (d, J = 5.1 Hz, 2 H), 7.62 (d, J = 6.9 Hz, 4 H), (m, 6 H), 7.15 (s, 2 H), 6.77 (d, J = 4.9 Hz, 2 H), 2.37 (s, 6 H); 13 C NMR (100 MHz, CDCl 3 ): 196.3, 152.0, 151.5, 150.0, 147.9, 139.7, 130.9, 128.9, 128.4, 120.4, 113.3, 108.9, 21.1; IR (KBr, cm -1 ) 3275, 3058, 2984, 2850, 1907, 1632, 1552, 1472, 1381, 1261, 1112, 1029, 819, 728; ESI-HRMS Calcd for C 30 H 27 N 4 O 2 S [M + H] , found ,2'-Thiobis(5,5-dimethyl-3-(phenylamino)cyclohex-2-en-1-one) (6a). 3 Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (s, 2 H), 7.41 (t, J = 7.7 Hz, 4 H), 7.29 (s, 1 H), (m, 5 H), 2.44 (s, 4 H), 2.37 (s, 4 H), 1.05 (s, 12 H); 13 C NMR (100 MHz, CDCl 3 ): 195.6, 167.7, 138.0, 129.4, 126.3, 124.7, 103.5, 49.5, 40.8, ,2'-Thiobis(3-((4-chlorophenyl)amino)-5,5-dimethylcyclohex-2-en-1-one) (6b). 3 S10
11 Yellow solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ (s, 2 H), 7.35 (d, J = 8.6 Hz, 4 H), 7.20 (d, J = 8.6 Hz, 4 H), 2.58 (s, 4 H), 2.38 (s, 4 H), 0.98 (s, 12 H); 13 C NMR (100 MHz, CDCl 3 ): 194.8, 167.0, 137.3, 131.2, 129.4, 125.7, 104.8, 50.5, 41.3, 32.7; IR (KBr, cm -1 ) 3064, 2957, 2938, 1600, 1590, 1492, 1382, 1277, 1120, 819, ,3'-Thiobis(4H-chromen-4-one) (8a) 4 White solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ 8.62 (s, 2 H), 8.17 (d, J = 8.0 Hz, 2 H), 7.66 (t, J = 8.0 Hz, 2 H), (m, 4 H); 13 C NMR (100 MHz, CDCl 3 ): 175.6, 159.6, 156.3, 133.9, 126.1, 125.7, 123.9, 118.3, 116.5; IR (KBr, cm -1 ) 3059, 1824, 1629, 1469, 1349, 1309, 1219, 1171, 1016, 888, ,3'-Thiobis(6-methyl-4H-chromen-4-one) (8b). 4 White solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ 8.59 (s, 2 H), 7.95 (s, 2 H), 7.45 (d, J = 8.4 Hz, 2 H), 7.33 (d, J = 8.4 Hz, 2 H), 2.42 (s, 6 H); 13 C NMR (100 MHz, CDCl 3 ): 175.7, 159.5, 154.6, 135.8, 135.1, 125.3, 123.6, 118.0, 116.3, ,3'-Thiobis(7-methoxy-4H-chromen-4-one) (8c). White solid; mp o C; 1 H NMR (400 MHz, CDCl 3 ): δ 8.53 (s, 2 H), 8.07 (d, J = 8.9 Hz, 2 H), 6.95 (d, J = 7.5 Hz, 2 H), 6.81 (s, 2 H), 3.88 (s, 6 H); 13 C NMR (100 MHz, CDCl 3 ): 175.0, 164.2, 159.2, 158.1, 127.4, 117.8, 116.5, 115.1, 100.4, 55.9; IR (KBr, cm -1 ) 3074, 1850, 1618, 1440, 1360, 1307, 1227, 1187, 1019, 941, 776; ESI-HRMS Calcd for C 20 H 15 O 6 S [M + H] , found S11
12 References (1) F. M. A. A. EL-Taweel and M. H. Elnagdi, J. Heterocyclic Chem., 2001, 38, 981. (2) G. W. Wang and C. B. Miao, Green Chem., 2006, 8, (3) L. F. Yang, C. G. Liu, X. P. Xu and S. J. Ji, Org. Biomol. Chem., 2016, 14, (4) W. Loewe and A. Kennemann, Archiv der Pharmazie, 1984, 317, S12
13 1 H and 13 C NMR spectra of all products 1 H and 13 C NMR spectra of 4a S13
14 1 H and 13 C NMR spectra of 4b O S O HN NH O S O HN NH S14
15 1 H and 13 C NMR spectra of 4c S15
16 1 H and 13 C NMR spectra of 4d S16
17 1 H and 13 C NMR spectra of 4e S17
18 1 H and 13 C NMR spectra of 4f S18
19 1 H and 13 C NMR spectra of 4g S19
20 1 H and 13 C NMR spectra of 4h S20
21 1 H and 13 C NMR spectra of 4i S21
22 1 H and 13 C NMR spectra of 4j S22
23 1 H and 13 C NMR spectra of 4k S23
24 1 H and 13 C NMR spectra of 4l S24
25 1 H and 13 C NMR spectra of 4m S25
26 1 H and 13 C NMR spectra of 4n S26
27 1 H and 13 C NMR spectra of 4o S27
28 1 H and 13 C NMR spectra of 4p O S O HN NH Br Br O S O HN NH Br Br S28
29 1 H and 13 C NMR spectra of 4q S29
30 1 H and 13 C NMR spectra of 4r O S O HN NH I I O S O HN NH I I S30
31 1 H and 13 C NMR spectra of 4s S31
32 1 H and 13 C NMR spectra of 4t S32
33 1 H and 13 C NMR spectra of 4u S33
34 1 H and 13 C NMR spectra of 6a S34
35 1 H and 13 C NMR spectra of 6b S35
36 1 H and 13 C NMR spectra of 8a S36
37 1 H and 13 C NMR spectra of 8b S37
38 1 H and 13 C NMR spectra of 8c S38
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Supplementary Material Control experiments S2 Characterization data for the products S2-S7 References S8 MR spectra for the products S9-S28 S1 Control experiments 2a (99.5 mg, 0.5 mmol), I 2 (50.8 mg,