Zinc Chloride Promoted Formal Oxidative Coupling of Aromatic Aldehydes and Isocyanides to α- Ketoamides
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1 Supporting information for Zinc Chloride Promoted Formal xidative Coupling of Aromatic Aldehydes and Isocyanides to α- Ketoamides Marinus Bouma, Géraldine Masson* and Jieping Zhu* Institut de Chimie des Substances aturelles, CRS, Gif-sur-Yvette Cedex, France S2: General information S3: General procedure S4-S12: Physical data of 1a-o and 7l S13-S34: Copies of 1 and 13 C MR spectra S35: PLC data of 1o S1
2 General Information: All reactions were carried out under argon atmosphere in dried glassware. All solvents were dried and distilled by standard procedures. Aldehydes and isocyanides were purchased from commercial suppliers and were used without further purification. All reactions were monitored by thin layer chromatography (TLC) plates (aluminium oxyde 60 F254, neutral) and analyzed with 254 nm UV light. Chromatography was performed using silica gel 60 ( mm). ptical rotations were measured with a polarimeter (589 nm). Melting points were determined on recrystallized product and are uncorrected. 1 MR were recorded on a 500 Mz instrument and 13 C MR were recorded on a 75 Mz instrument. Chemical shifts (δ) were reported in ppm relative to residual CCl 3 as an internal reference ( 1 : 7.26 ppm, 13 C: 77 ppm). Coupling constants (J) were reported in ertz (z). Peak multiplicity is indicated as follows: s (singlet), d (doublet), t (triplet), q (quartet), b (broad) and m (multiplet). The RMS data were measured on MALDI-TF type of instrument for the high resolution mass spectra (RMS). Infrared spectra were recorded on IR spectrometer, and absorption frequencies were reported in reciprocal centimeters (cm -1 ). The known products were characterized by comparing the 1 MR, 13 C MR and melting points data with those reported in the literature. S2
3 General procedure for α-ketoamide synthesis from aldehyde and isocyanide: To a solution of freshly dried ZnCl 2 (3.0 eq.) and the aldehyde (1.0 eq.) in dry TF (1.0 M), was added -methyl hydroxylamine hydrochloride (1.6 eq.) and ac3 (1.6 eq.). The mixture was stirred for 30 min at room temperature. The isocyanide (2.0 eq.) and acetic acid (3.0 eq.) were then added, and the mixture was stirred at room temperature for 48 hours. The reaction mixture was then diluted with ethyl acetate and filtered, the solvent was removed in vacuo, and the crude product was purified by flash chromatography on silica gel. S3
4 Compound 1a: Yield: 64% Aspect: White crystals Melting point: C. IR (cm -1 ): 3310 (), 2969, 1666 (C), 1517, 1449, 1366, 1239, 751. MR 1 δ (500 Mz, CDCl 3, 293K): 8.32 (d, 2, J = 7.6z), 7.62 (t, 1, J = 7.4z,), 7.48 (dd, 2, J = 7.6z, J = 7.4z,), 6.95 (bs, 1), 1.47 (s, 9). MR 13 C δ (75 Mz, CDCl 3, 293K): (Cq), (Cq), (C), (Cq), (2x C), (2x C), 51.6 (Cq), 28.3 (3x C 3 ). RMS (ESI): calculated for [M+a] +, C a m/z = , found m/z = S4
5 Compound 1b: Yield: 61% Aspect: White crystals Melting point: C. IR (cm -1 ): 3324 (), 2969, 2930, 1660 (C), 1587, 1365, 1239, 1173, 1090, 1006, 838, 793. MR 1 δ (500 Mz, CDCl 3, 293K): 8.31 (d, 2, J = 8.6z), 7.45 (d, 2, J = 8.6z), 6.98 (bs, 1), 1.46 (s, 9). MR 13 C δ (75 Mz, CDCl 3, 293K): (Cq), (Cq), (Cq), (2x C), (Cq), (2x C), 51.7 (Cq), 28.3 (3x C 3 ). RMS (ESI): calculated for [M+a] +, C acl m/z = , found m/z = S5
6 Compound 1c: Yield: 53% Aspect: Colourless oil IR (cm -1 ): 3317 (), 2970, 1666 (C), 1514, 1365, 1232, 1195, 751. MR 1 δ (500 Mz, CDCl 3, 293K): 8.47 (s, 1), 8.28 (d, 1, J = 7.8z), 7.74 (d, 1, J = 7.9z), (m, 1), 6.97 (bs, 1), 1.47 (s, 9). MR 13 C δ (75 Mz, CDCl 3, 293K): (Cq ), (Cq), (C), (Cq), (C), (C), (C), (Cq), 51.7 (Cq), 28.3 (3x C 3 ). RMS (ESI): calculated for [M+a] +, C Br 2 a 79 Br = , found m/z = ; calculated for [M+a] +, C Br 2 a 81 Br = , found m/z = S6
7 Compound 1d: Yield: 58% Aspect: Colourless oil IR (cm -1 ): 3286 (), 2980, 1680, 1647 (C), 1606, 1555, 1449, 1364, 1242, 1221, 1173, 1009, 857, 779, 668. MR 1 δ (500 Mz, CDCl 3, 293K): 8.23 (d, 2, J = 8.2z), 7.26 (d, 2, J = 8.2z), 6.97 (bs, 1), 2.41 (s, 3), 1.46 (s, 9). MR 13 C δ (75 Mz, CDCl 3, 293K): (Cq), (Cq), (Cq), (2x C), (Cq), (2x C), 51.5 (Cq), 28.4 (3x C 3 ), 21.7 (C 3 ). RMS (ESI): calculated for [M+a] +, C a m/z = , found m/z = S7
8 Compound 1e: Yield: 50% Aspect: White crystals Melting point: C. IR (cm -1 ): 3334 (), 2964, 1650 (C), 1601, 1531, 1453, 1362, 1240, 1176, 1054, 1007, 861, 841, 804, 724. MR 1 δ (500 Mz, CDCl 3, 293K): 8.24 (d, 2, J = 8.4z), 7.32 (d, 1, J = 8.4z), 6.95 (bs, 1), 2.96 (td, 1, J = 13.8z, J = 6.9z), 1.46 (s, 9), 1.26 (d, 6). MR 13 C δ (75 Mz, CDCl 3, 293K): (Cq), (Cq), (Cq), (2x C), (Cq), (2x C), 51.5 (Cq), 34.3 (C), 28.3 (3xC 3 ), 23.5 (2x C 3 ). RMS (ESI): calculated for [M+a] +, C a m/z = , found m/z = S8
9 Compound 1f: Yield: 46% Aspect: White crystals Melting point: 84 C. IR (cm -1 ): 3328 (), 2972, 2355, 1655 (C), 1624, 1515, 1458, 1366, 1227, 1175, 1126, 804, 744, 668. MR 1 δ (500 Mz, CDCl 3, 293K): 9.19 (s, 1), 8.19 (d, 1, J = 8.7z), 8.01 (d, 1, J = 8.1z), (m, 2), (m, 1), (m, 1), 7.08 (bs, 1), 1.51 (s, 9). MR 13 C δ (75 Mz, CDCl 3, 293K): (Cq), (Cq), (Cq), (C), (Cq), (Cq), (C), (C), (C), (C), (C), (C), 51.6 (Cq), 28.4 (3x C 3 ). RMS (ESI): calculated for [M+a] +, C a m/z = , found m/z = S9
10 Compound 1g: Yield: 52% Aspect: White crystals Melting point: C. IR (cm -1 ): 3316 (), 2969, 2925, 1660 (C), 1516, 1250, 1218, 1165, 772, 750. MR 1 δ (500 Mz, CDCl 3, 293K): (m, 2), 7.43 (d, 1, J = 7.6z), 7.36 (dd, 1, J = 7.6z, J = 7.6z), 6.95 (bs, 1), 2.41 (s, 3), 1.47 (s, 9). MR 13 C δ (75 Mz, CDCl 3, 293K): (Cq), (Cq), (Cq), (C), (Cq), (C), (C), (C), 51.6 (Cq), 28.3 (3x C 3 ), 21.3 (C 3 ). RMS (ESI): calculated for [M+a] +, C a = , found m/z = S10
11 Compound 1h: Yield: 31% Aspect: Yellow oil IR (cm -1 ): 3388 (), 2971, 2926, 1673 (C), 1612, 1531, 1349, 1235, 1098, 750. MR 1 δ (500 Mz, CDCl 3, 293K): 9.18 (s, 1), 8.71 (d, 1, J = 7.7z), 8.48 (d, 1, J = 8.3z), 7.69 (dd, 1, J = 7.7z, J = 8.3z), 7.03 (bs, 1), 1.49 (s, 9). MR 13 C δ (75 Mz, CDCl 3, 293K): (Cq), (Cq), (Cq), (C), (Cq), (C), (C), (C), 52.0 (Cq), 28.3 (3x C 3 ). RMS (ESI): calculated for [M+a] +, C a = , found m/z = S11
12 Compound 1i: Yield: 31% Aspect: Colourless oil IR (cm -1 ): 3327 (), 2968, 2360, 1671 (C), 1517, 1455, 1366, 1238, 1216, 1005, 846, 750, 666. MR 1 δ (500 Mz, CDCl 3, 293K): 7.89 (d, 1), 7.44 (dd, 1, J = 7.6z, J = 7.6z), (m, 2), 6.93 (bs, 1), 2.49 (s, 3), 1.48 (s, 9). MR 13 C δ (75 Mz, CDCl 3, 293K): (Cq), (Cq), (Cq), (Cq), (C), (C), (C), (C), 51.6 (Cq), 28.3 (3x C 3 ), 20.7 (C 3 ). RMS (ESI): calculated for [M+a] +, C a = , found m/z = S12
13 Compound 1j: Yield: 61% Aspect: Pale yellow oil IR (cm -1 ): 3178 (), 3026, 1660 (C), 1592, 1510, 1469, 1260, 1216, 1162, 1026, 745, 666. MR 1 δ (500 Mz, CDCl 3, 293K): (m, 3), (m, 3), 7.00 (d, 2, J = 9.0z), 3.93 (s, 3), 2.32 (s, 6). MR 13 C δ (75 Mz, CDCl 3, 293K): (Cq), (Cq), (Cq), (2x Cq), (2x C), (Cq), (2x C), (C), (Cq), (2x C), 55.6 (C 3 ), 18.5 (2x C 3 ). RMS (ESI): calculated for [M+a] +, C a m/z = , found m/z = S13
14 Compound 1k: Yield: 50% Aspect: Yellow crystals Melting point: 117 C. IR (cm -1 ): 3178 (), 3042, 1682 (C), 1626, 1540, 1469, 1426, 1217, 1189, 1075, 896, 735, 702. MR 1 δ (500 Mz, CDCl 3, 293K) (m, 2), 8.37 (d, 1, J = 7.8z), 7.65 (d, 1, J = 8.0z), 7.48 (dd, J = 7.8z, J = 8.0z, 1), 2.31 (s, 6). MR 13 C δ (75 Mz, CDCl 3, 293K) (Cq), (Cq), (2x Cq), (Cq), (Cq), (C), (Cq), (C), (C), (C), (2x C), (C), 18.5 (2x C 3 ). RMS (ESI): calculated for [M+a] +, C acl = , found m/z = S14
15 Compound 1l: Yield: 44% Aspect: Colourless oil IR (cm -1 ): 3390 (), 2954, 1659 (C), 1597, 1514, 1262, 1241, 1215, 1168, 1031, 754. MR 1 δ (500 Mz, CDCl 3, 293K): 8.41 (d, 2, J = 9.0z), 7.08 (bs, 1), 6.94 (d, 2, J = 9.0z), 3.89 (s, 3), 1.83 (s, 2), 1.52 (s, 6), 1.05 (s, 9). MR 13 C δ (75 Mz, CDCl 3, 293K): (Cq), (Cq), (Cq), (2x C), (Cq), (2x C), 55.5 (C 3 ), 55.3 (Cq), 51.6 (C 2 ), 31.7 (Cq), 31.4 (3x C 3 ), 28.7 (2x C 3 ). RMS (ESI): calculated for [M+a] +, C a m/z = , found m/z = S15
16 Compound 1m: Yield: 58% Aspect: White crystals Melting point: C. IR (cm -1 ): 3302 (), 2904, 2846, 1668 (C), 1643, 1599, 1573, 1537, 1453, 1265, 1218, 1169, 1092, 1026, 854, 799, 790. MR 1 δ (500 Mz, CDCl 3, 293K): 8.39 (d, 2, J = 9.0z), 6.93 (d, 2, J = 9.0z), 6.86 (bs, 1), 3.89 (s, 3), (m, 9), (m, 6). MR 13 C δ (75 Mz, CDCl 3, 293K): (Cq), (Cq), (Cq), (2x C), (Cq), (2x C), 55.5 (C 3 ), 51.2 (Cq), 41.1 (3x C 2 ), 36.2 (3x C), 29.3 (3x C 3 ). RMS (ESI): calculated for [M+a] +, C a m/z = , found m/z = S16
17 Compound 1n: Yield: 67% Aspect: White crystals Melting point: C. IR (cm -1 ): 3318 (), 3063, 2928, 1659 (C), 1595, 1518, 1449, 1218, 1177, 746, 688. MR 1 δ (500 Mz, CDCl 3, 293K): 8.37 (d, 2, J = 7.4z), 7.63 (t, 1, J = 7.4z), 7.49 (dd, 2, J = 7.4z, J = 7.4z), 7.42 (bs, 1), (m, 5), 4.58 (d, 2, J = 6.0z). MR 13 C δ (75 Mz, CDCl 3, 293K): (Cq), (Cq), (Cq), (C), (Cq), (2x C), (2x C), (2x C), (2x C), (Cq), 43.4 (C 2 ). RMS (ESI): calculated for [M+a] +, C a m/z = , found m/z = S17
18 Compound 1o: Yield: 35% Aspect: Yellow oil IR (cm -1 ): 3294 (), 3064, 3030, 2975, 2926, 1660 (C), 1566, 1514, 1211, 760, 698. MR 1 δ (500 Mz, CDCl 3, 293K): 8.37 (s, 1), 8.28 (d, 1, J = 7.8z), 7.60 (d, 1, J = 7.1z), (m, 6), 7.33 (dd, J = 7.8z, J = 7.1z, 1), (m, 1), 1.63 (d, 3, J = 6.9z). MR 13 C δ (75 Mz, CDCl 3, 293K): (Cq), (Cq), (Cq), (Cq), (Cq), (C), (C), (C), (Cq), (2x C), (C), (2x C), 49.2 (C), 21.6 (C 3 ). RMS (ESI): calculated for [M+a] +, C acl = , found m/z = S18
19 Compound 1a ppm (f1) S19
20 Compound 1b Cl Cl S20
21 Compound 1c Br Br ppm (f1) S21
22 Compound 1d ppm (f1) ppm (f1) S22
23 Compound 1e ppm (f1) S23
24 Compound 1f ppm (f1) S24
25 Compound 1g S25
26 Compound 1h S26
27 Compound 1i ppm (f1) S27
28 Compound 1j S28
29 Compound 1k Cl Cl ppm (f1) S29
30 Compound 1l S30
31 Compound 1m S31
32 Compound 1n S32
33 Compound 1o Cl Cl S33
34 Compound 7l 2 ppm (f1) S34
35 PLC Chromatograms of compound 1o mau mau Minutes DAD-C1 254 nm Results Pk # Retention Time Area Area % mau 1 mau Minutes DAD-C1 254 nm Results Pk # Retention Time Area Area % S35
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