Supporting Information
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- Δαμιανός Στεφανόπουλος
- 5 χρόνια πριν
- Προβολές:
Transcript
1 Supporting Information for Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolecular [1,5]-hydride shift/isomerization reaction Chun-Huan Jiang, Xiantao Lei, Le Zhen, Hong-Jin Du, Xiaoan Wen, Qing-Long Xu* and Hongbin Sun* Address: State Key Laboratory of Natural Medicines and Jiangsu Key Laboratory of Drug Discovery for Metabolic Disease, China Pharmaceutical University, 24 Tongjia Xiang, Nanjing , China Qing-Long Xu - xuqing307@126.com, Hongbin Sun - hbsun2000@yahoo.com *Corresponding author Experimental details, analytical data, and copies of the 1 H and 13 C NMR spectra of the final products Table of Contents General information...s2 General procedure for the preparation of compound 1...S2 General procedure for the preparation of N-arylpyrroles...S3 References...S11 Copies of NMR spectra...s12 S1
2 General information 1 H NMR (300 MHz) spectra were recorded on a Bruker Avance 300 spectrometer in CDCl 3 [using (CH 3 ) 4 Si (for 1 H, δ = 0.00) as internal standard]. 13 C NMR (75 MHz) spectra on a Bruker Avance 300 spectrometer in CDCl 3 [using CDCl 3 (for 13 C, δ = 77.00) as internal standard]. The following abbreviations were used to describe peak splitting patterns when appropriate: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, dd = doublet of doublets, dt = doublet of triplets, ddd = doublet of doublet of doublets, td = triplet of doublets. High and low resolution mass spectra were obtained with a ESI mass spectrometer and a TOF mass analyzer. Melting points are uncorrected. Commercially available reagents and solvents were used without further purification. Flash column chromatography was performed using silica gel ( mesh, Qingdao Ocean Chemical Company, China). Reactions were monitored by TLC on silica gel 60 F254 plates (Qingdao Ocean Chemical Company, China); visualization was effected by ultraviolet light (254 nm). General procedure for the preparation of compound 1 [1] To a solution of 2-fluorobenzaldehyde 4a (1.8 g, 14.5 mmol, 1.0 equiv) in DMF was added K 2 CO 3 (2.0 g, 14.5 mmol, 1.0 equiv) and 3-pyrroline 5 (1.0 g, 14.5 mmol, 1.0 equiv) at rt, then the mixture was heated to 90 o C and stirred for 7 h. The mixture was filtered and the filtrate was concentrated and the residue was purified by column chromatography (PE/EA 25:1) to give the title compound 1 (1.55 g, 62% yield). S2
3 General procedure for the preparation of N-arylpyrroles A mixture of benzaldehyde 1 ( mmol), amine 2 (1.2 equiv) and ZnCl 2 (5 mol %) were stirred in dichloromethane or DCE (5.0 ml) at room temperature or reflux and monitored by TLC. After the completion of the reaction (about 24 h), the organic solvent was removed by evaporation and the residue was purified by flash column chromatography on silica gel to give N-arylpyrrole 3. 3a, 93% yield, light yellow solid (R f = 0.85, petroleum ether/ethyl acetate, 50/3), m.p o C. 1 H-NMR (300 MHz, CDCl 3 ) δ 7.87 (d, J = 7.6 Hz, 1H), (m, 13H), 6.73 (t, J = 2.0 Hz, 2H), 6.30 (t, J = 2.0 Hz, 2H), 3.43 (s, 4H), 3.40 (s, 2H). 13 C-NMR (75 MHz, CDCl 3 ) δ 140.6, 139.4, 135.8, 130.0, 128.7, 128.2, 127.8, 127.2, 126.9, 126.7, 122.5, 108.8, 58.1, MS (ESI): m/z [M+H] + ; HRMS (ESI): Exact mass calcd. for C 25 H 25 N 2 [M+H] , Found: b, 92% yield, light yellow oil (R f = 0.85, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ 7.72 (d, J = 7.9 Hz, 1H), (m, 8H), 7.19 (t, J = 6.9 Hz, 3H), 7.02 (s, 1H), 6.73 (t, J = 1.9 Hz, 2H), 6.29 (t, J = 1.9 Hz, 2H), 3.42 (s, 4H), 3.37 (s, 2H), 2.32 (s, 3H). 13 C NMR (75 MHz, CDCl 3 ) δ 140.4, 139.5, 137.2, 132.4, 129.8, 128.7, 128.5, 128.2, 127.2, 126.8, 122.5, 108.7, 58.0, 52.4, MS (ESI): m/z [M+Na] + ; HRMS (ESI): Exact mass calcd. for C 26 H 26 N 2 Na [M+Na] , Found: S3
4 3c, 97% yield, light yellow oil (R f = 0.85, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ 7.71 (d, J = 8.6 Hz, 1H), (m, 10H), 6.94 (dd, J = 8.6, 2.3 Hz, 1H), 6.76 (s, 3H), 6.30 (s, 2H), 3.76 (s, 3H), 3.42 (s, 4H), 3.34 (s, 2H). 13 C NMR (75 MHz, CDCl 3 ) δ 158.6, 141.4, 139.5, 131.1, 128.7, 128.2, 127.4, 126.8, 122.5, 114.1, 111.6, 108.8, 57.9, 55.4, MS (ESI): m/z [M+Na] + ; HRMS (ESI): Exact mass calcd. for C 26 H 26 N 2 ONa [M+Na] , Found: d, 89% yield, light yellow oil (R f = 0.85, petroleum ether/ethyl acetate, 50/3),. 1 H NMR (300 MHz, CDCl 3 ) δ 8.02 (d, J = 8.1 Hz, 1H), 7.62 (d, J = 8.2 Hz, 1H), 7.47 (s, 1H), (m, 10H), 6.72 (t, J = 2.0 Hz, 2H), 6.33 (t, J = 2.0 Hz, 2H), 3.45 (s, 6H). 13 C NMR (75 MHz, CDCl 3 ) δ 140.7, 140.1, 138.9, 130.5, (q, J = 32.9 Hz), 128.7, 128.4, 127.1, (q, J = 3.6 Hz), (q, J = Hz), (q, J = 3.7 Hz), 122.4, 109.6, 58.3, MS (ESI): m/z [M+Na] + ; HRMS (ESI): Exact mass calcd. for C 26 H 23 F 3 N 2 Na [M+Na] , Found: e, 91% yield, light yellow oil (R f = 0.85, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ 8.78 (d, J = 2.1 Hz, 1H), 8.06 (dd, J = 8.6, 2.3 Hz, 1H), (m, 11H), 6.76 (s, 2H), 6.36 (s, 2H), 3.55 (s, 2H), 3.49 (s, 4H). 13 C NMR (75 MHz, CDCl 3 ) δ 146.6, 145.3, 138.5, 136.8, 128.8, 128.4, 127.2, 126.8, 125.8, 122.5, 122.2, 110.3, 58.5, MS (ESI): m/z [M+Na] + ; HRMS (ESI): Exact mass calcd. for C 25 H 23 N 3 O 2 Na [M+Na] , Found: S4
5 3f, 71% yield, light yellow oil (R f = 0.85, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ 7.84 (d, J = 1.8 Hz, 1H), (m, 8H), (m, 3H), 7.09 (d, J = 8.4 Hz, 1H), 6.66 (s, 2H), 6.29 (s, 2H), 3.42 (s, 4H), 3.35 (s, 2H). 13 C NMR (75 MHz, CDCl 3 ) δ 139.0, 138.9, 137.8, 133.6, 129.7, 128.7, 128.3, 127.9, 127.4, 127.1, 122.4, 109.2, 58.2, MS (ESI): m/z [M+H] + ; HRMS (ESI): Exact mass calcd. for C 25 H 24 ClN 2 [M+H] , Found: g, 87% yield, light yellow oil (R f = 0.85, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ 7.79 (d, J = 8.4 Hz, 1H), (m, 12H), (m, 2H), (m, 2H), 3.42 (s, 4H), 3.36 (s, 2H). 13 C NMR (75 MHz, CDCl 3 ) δ 141.4, 139.1, 134.2, 132.5, 131.2, 128.7, 128.3, 127.9, 127.0, 126.6, 122.3, 109.4, 58.1, MS (ESI): m/z [M+H] + ; HRMS (ESI): Exact mass calcd. for C 25 H 24 ClN 2 [M+H] , Found: h, 87% yield, light yellow oil (Rf = 0.85, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ 7.72 (d, J = 8.4 Hz, 1H), 7.46 (dd, J = 8.3, 1.9 Hz, 1H), (m, 11H), (m, 2H), (m, 2H), 3.41 (s, 4H), 3.34 (s, 2H). 13 C NMR (75 MHz, CDCl 3 ) δ 141.6, 139.0, 134.8, 131.4, 130.8, 129.5, 128.6, 128.3, 127.0, 122.3, 120.2, 109.4, 58.1, MS (ESI): m/z [M+H] + ; HRMS (ESI): Exact mass calcd. for C 25 H 24 BrN 2 [M+H] , Found: S5
6 3i, 78% yield, light yellow solid (R f = 0.85, petroleum ether/ethyl acetate, 50/3), m.p o C 1 H NMR (300 MHz, CDCl 3 ) δ 7.99 (d, J = 2.2 Hz, 1H), (m, 11H), 7.04 (d, J = 8.4 Hz, 1H), (m, 2H), (m, 2H), 3.43 (s, 4H), 3.36 (s, 2H). 13 C NMR (75 MHz, CDCl 3 ) δ 139.5, 138.9, 138.0, 132.8, 130.3, 128.7, 128.3, 128.1, 127.1, 122.3, 121.6, 109.3, 58.2, MS (ESI): m/z [M+H] + ; HRMS (ESI): Exact mass calcd. for C 25 H 24 BrN 2 [M+H] , Found: j, 87% yield, light yellow oil (R f = 0.87, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ 7.57 (d, J = 4.3 Hz, 1H), (m, 7H), (m, 6H), 6.78 (s, 2H), 6.33 (s, 2H), 4.80 (s, 2H). 13 C NMR (75 MHz, CDCl 3 ) δ 147.8, 139.5, 135.1, 129.2, 128.1, 127.8, 127.5, 127.1, 122.1, 121.5, 120.6, 109.3, MS (ESI): m/z [M+Na] + ; HRMS (ESI): Exact mass calcd. for C 23 H 20 N 2 Na [M+Na] , Found: k, 81% yield, light yellow oil (R f = 0.35, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ 7.66 (d, J = 7.6 Hz, 1H), (m, 3H), 6.84 (t, J = 1.8 Hz, 2H), 6.29 (t, J = 1.8 Hz, 2H), 3.39 (s, 2H), 2.44 (q, J = 7.1 Hz, 4H), 0.94 (t, J = 7.1 Hz, 6H). 13 C NMR (75 MHz, CDCl 3 ) δ 140.6, 136.1, 130.5, 127.4, 127.1, 126.6, 122.7, 108.6, 52.5, 46.8, MS (ESI): m/z [M+H] + ; HRMS (ESI): Exact mass calcd. for C 15 H 21 N 2 [M+H] , Found: S6
7 3l, 82% yield, light yellow oil (R f = 0.50, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ 7.66 (d, J = 7.4 Hz, 1H), (m, 3H), 6.82 (t, J = 1.8 Hz, 2H), 6.29 (t, J = 1.8 Hz, 2H), 3.37 (s, 2H), 2.32 (t, J = 7.1 Hz, 4H), (m, 8H), 0.85 (t, J = 7.1 Hz, 6H). 13 C NMR (75 MHz, CDCl 3 ) δ 140.5, 136.3, 130.5, 127.4, 127.0, 126.5, 122.6, 108.6, 53.6, 29.1, 20.6, HRMS MS (ESI): m/z [M+H] + ; HRMS (ESI): Exact mass calcd. for C 19 H 29 N 2 [M+H] , Found: m, 89% yield, light yellow oil (R f = 0.75, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ 7.30 (s, 4H), (m, 2H), 6.81 (t, J = 2.0 Hz, 2H), (m, 3H), 6.33 (t, J = 2.0 Hz, 2H), 4.35 (s, 2H), 2.94 (s, 3H). 13 C NMR (75 MHz, CDCl 3 ) δ 149.5, 139.8, 134.9, 129.1, 128.0, 127.6, 127.5, 127.0, 122.1, 116.6, 112.1, 109.2, 52.6, MS (ESI): m/z [M+Na] + ; HRMS (ESI): Exact mass calcd. for C 18 H 18 N 2 Na [M+Na] , Found: n, 88% yield, light yellow oil (R f = 0.75, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), 7.16 (t, J = 8.0 Hz, 2H), 6.83 (t, J = 1.9 Hz, 2H), (m, 3H), 6.34 (t, J = 1.9 Hz, 2H), 4.33 (s, 2H), 3.40 (q, J = 7.0 Hz, 2H), 1.13 (t, J = 7.0 Hz, 3H). 13 C NMR (75 MHz, CDCl 3 ) δ 148.2, 139.8, 135.2, 129.2, 128.0, 127.6, 127.4, 127.0, 122.1, 116.2, 112.0, 109.2, 50.0, 45.2, MS (ESI): m/z [M+Na] + ; HRMS (ESI): Exact mass calcd. for C 19 H 20 N 2 Na [M+Na] , Found: S7
8 3o, 94% yield, light yellow oil (R f = 0.70, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ 7.67 (d, J = 7.3 Hz, 1H), (m, 8H), 6.88 (t, J = 2.1 Hz, 2H), 6.31 (t, J = 2.0 Hz, 2H), 3.44 (s, 2H), 3.37 (s, 2H), 2.07 (s, 3H). 13 C NMR (75 MHz, CDCl 3 ) δ , 139.3, 135.0, 130.6, 128.8, 128.2, 127.5, 127.4, , 126.6, , 108.7, 61.8, 56.8, MS (ESI): m/z [M+Na] + ; HRMS (ESI): Exact mass calcd. for C 19 H 20 N 2 Na [M+Na] , Found: p, 88% yield, light yellow oil (R f = 0.40, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ (m, 4H), (m, 2H), 6.81 ((t, J = 2.1 Hz, 2H), (m, 3H), 6.34 (t, J = 2.1 Hz, 2H), 4.41 (s, 2H), 3.73 (t, J = 5.7 Hz, 2H), 3.51 (t, J = 5.8 Hz, 2H). 13 C NMR (75 MHz, CDCl 3 ) δ 148.4, 139.9, 134.6, 129.3, 128.1, 127.6, 127.5, 127.2, 122.1, 117.2, 112.8, 109.3, 60.1, 53.4, MS (ESI): m/z [M+Na] + ; HRMS (ESI): Exact mass calcd. for C 19 H 20 N 2 ONa [M+Na] , Found: p, 77% yield, light yellow oil (R f = 0.45, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ 7.55 (d, J = 6.7 Hz, 1H), (m, 3H), 6.94 (d, J = 0.9 Hz, 2H), 6.30 (d, J = 0.9 Hz, 2H), 3.45 (s, 2H), 2.45 (s, 4H), 1.74 (s, 4H). 13 C NMR (75 MHz, CDCl 3 ) δ 140.4, 135.0, 130.6, 127.4, 127.2, 126.4, 122.8, 108.7, 55.2, 53.9, MS (ESI): m/z [M+H] + ; HRMS (ESI): Exact mass calcd. for C 15 H 19 N 2 [M+H] , Found: S8
9 3r, 84% yield, light yellow oil (R f = 0.45, petroleum ether/ethyl acetate, 50/3). 1 H NMR (500 MHz, CDCl 3 ) δ 7.54 (d, J = 7.1 Hz, 1H), (m, 3H), 6.93 (t, J = 2.0 Hz, 2H), (d, J = 2.0 Hz, 2H), 3.26 (s, 2H), 2.31 (s, 4H), (m, 4H), 1.40 (d, J = 4.4 Hz, 2H). 13 C NMR (75 MHz, CDCl 3 ) δ 141.0, 134.4, 130.9, 127.4, 127.1, 126.5, 122.8, 108.6, 58.4, 54.3, 26.1, MS (ESI): m/z [M+H] + ; HRMS (ESI): Exact mass calcd. for C 16 H 21 N 2 [M+H] , Found: s, 98% yield, light yellow oil (R f = 0.40, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ 7.50 (dd, J = 4.9, 4.0 Hz, 1H), 7.30 (dt, J = 10.2, 3.4 Hz, 3H), (m, 2H), (m, 2H), 3.66 (t, J = 4.5 Hz, 4H), 3.30 (s, 2H), 2.38 (t, J = 4.4 Hz, 4H). 13 C NMR (75 MHz, CDCl 3 ) δ 141.1, 133.2, 131.0, 127.8, 127.0, 126.7, 122.7, 108.7, 67.0, 58.1, MS (ESI): m/z [M+Na] + ; HRMS (ESI): Exact mass calcd. for C 15 H 18 N 2 ONa [M+Na] , Found: t, 84% yield, light yellow oil (R f = 0.85, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ 7.55 (dd, J = 5.8, 2.9 Hz, 1H), (m, 3H), 7.06 (d, J = 7.2 Hz, 1H), 7.00 (t, J = 7.7 Hz, 1H), 6.85 (t, J = 2.1 Hz, 2H), 6.65 (t, J = 7.3 Hz, 1H), 6.35 (d, J = 7.8 Hz, 1H), 6.29 (t, J = 2.1 Hz, 2H), 4.05 (s, 2H), 3.24 (t, J = 8.3 Hz, 2H), 2.92 (t, J = 8.2 Hz, 2H). 13 C NMR (75 MHz, CDCl 3 ) δ 152.2, 140.3, 134.1, 129.9, 129.6, 127.8, 127.7, 127.2, 126.9, 124.4, 122.4, 117.9, 109.1, 107.1, 53.8, 49.5, MS (ESI): m/z [M+Na] + ; HRMS (ESI): Exact mass calcd. for C 19 H 18 N 2 Na [M+Na] , Found: S9
10 3u, 88% yield, light yellow oil (R f = 0.90, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ (m, 1H), 7.29 (m, 3H), 6.94 (t, J = 7.1 Hz, 2H), 6.82 (t, J = 2.1 Hz, 2H), 6.56 (t, J = 7.3 Hz, 1H), 6.36 (s, 1H), 6.33 (t, J = 2.0 Hz, 2H), 4.29 (s, 3H), 3.26 (t, J = 5.7 Hz, 3H), 2.78 (t, J = 6.2 Hz, 3H), (m, 3H). 13 C NMR (75 MHz, CDCl 3 ) δ 145.4, 139.9, 134.7, 129.0, 128.0, 127.4, 127.1, , 122.2, 122.1, 116.0, 110.7, 109.2, 51.4, 49. 9, 28.1, MS (ESI): m/z [M+Na] + ; HRMS (ESI): Exact mass calcd. for C 20 H 20 N 2 [M+Na] , Found: v, 76% yield, light yellow oil (R f = 0.70, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ (m, 1H), (m, 3H), (m, 3H), (m, 3H), (m, 2H), 3.58 (s, 2H), 3.48 (s, 2H), 2.87 (t, J = 5.7 Hz, 2H), 2.68 (t, J = 5.8 Hz, 2H). 13 C NMR (75 MHz, CDCl 3 ) δ 141.0, 134.9, 134.4, 134.0, 130.8, 128.6, 127.7, 127.3, 126.7, 126.5, 126.0, 125.5, 122.8, 108.8, 57.6, 55.8, 50.4, MS (ESI): m/z [M+Na] + ; HRMS (ESI): Exact mass calcd. for C 20 H 20 N 2 Na [M+Na] , Found: w, 98% yield, light yellow oil (R f = 0.35, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, CDCl 3 ) δ (m, 1H), (m, 8H), 6.85 (t, J = 1.9 Hz, 2H), 6.29 (t, J = 1.9 Hz, 2H), 3.68 (s, 2H), 3.65 (s, 2H). 13 C NMR (75 MHz, CDCl 3 ) δ 140.3, 140.0, 135.7, 130.0, 128.2, 128.0, 127.7, 127.5, 126.8, 126.6, 122.2, 109.0, 53.3, MS (ESI): m/z [M+Na] + ; HRMS (ESI): Exact mass calcd. for C 18 H 18 N 2 Na [M+Na] , Found: S10
11 3x, 33% yield, light yellow oil (R f = 0.35, petroleum ether/ethyl acetate, 50/3). 1 H NMR (300 MHz, d 6 -DMSO) δ (m, 1H), (m, 3H), (m, 2H), (m, 2H), 3.66 (s, 2H), 2.49 (t, J = 6.9 Hz, 2H), (m, 2H), 1.27 (dt, J = 13.8, 6.7 Hz, 2H), 0.87 (t, J = 7.1 Hz, 3H). 13 C NMR (75 MHz, CDCl 3 ) δ 140.2, 136.1, 129.9, 127.6, 126.7, 122.3, 109.0, 49.8, 49.2, 32.1, 20.4, MS (ESI): m/z [M+Na] + ; HRMS (ESI): Exact mass calcd. for C 15 H 20 N 2 Na [M+Na] , Found: y, 99% yield, light yellow solid (R f = 0.60, petroleum ether/ethyl acetate, 50/3), m.p o C. 1 H NMR (500 MHz, CDCl 3 ) δ (m, 1H), (m, 3H), 7.10 (t, J = 7.8 Hz, 2H), (m, 2H), 6.66 (t, J = 7.2 Hz, 1H), 6.49 (d, J = 8.1 Hz, 2H), (m, 2H), 4.18 (s, 2H), 3.74 (s, 1H). 13 C NMR (75 MHz, CDCl 3 ) δ 147.6, 140.1, 134.8, 129.4, 129.1, 128.0, 127.8, 126.8, 122.1, 117.6, , 109.4, MS (ESI): m/z [M+H] + ; HRMS (ESI): Exact mass calcd. for C 17 H 17 N 2 [M+H] , Found: References: [1] Han, Y.-Y.; Han, W.-Y.; Hou, X.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2012, 14, S11
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