Supporting Information for. Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of. 3,5-Disubstituted Pyridines: Mechanistic Studies
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1 Supporting Information for Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of 3,5-Disubstituted Pyridines: Mechanistic Studies Ta-Hsien Chuang* a, Yu-Chi Chen b and Someshwar Pola c thchuang@mail.cmu.edu.tw a School of Pharmacy, China Medical University, Taichung, 40402, Taiwan, ROC b Department of Cosmetic Science, Vanung University, No.1 Van-Nung Rd., Chung-Li, Tao-Yuan 32045, Taiwan, ROC c Department of Chemistry, Kakatiya University, Warangal, India Table of contents Experimental procedures and characterization References for known compounds Page S2-S5 S5 1 H and 13 C NMR spectra S6 following S1
2 Experimental General All reagents were purchased and used without further purification. Nuclear magnetic resonance spectra were recorded on 300 MHz and 400 MHz FT-NMR spectrometers; all chemical shifts were reported in ppm from tetramethylsilane as an internal standard. Column chromatography was carried out using mesh silica gel and mesh neutral aluminum oxide. (E)-[2-13 C]Cinnamic acid (3a- 13 C). A mixture of [2-13 C]malonic acid (0.21 g, 2 mmol), benzaldehyde (0.46 g, 4 mmol) and a catalytic amount of piperidine in dry pyridine (10 ml) was heated at 90 o C for 9h. After cooling, the resulting solution was poured to ice-water, acidified with conc. HCl and allowed to precipitate a white solid. The solid was filtered and washed with cold water to give pure 3a- 13 C. Yield 51%; white solid, mp o C (hexane-ch 2 Cl 2 ) (lit. 1 mp o C). 1 H NMR (CDCl 3 ) δ 6.46 (1H, dd, J = 162.8, 16.0 Hz), 7.41 (3H, m), 7.56 (2H, m), 7.80 (1H, dd, J = 16.0, 2.9 Hz); 13 C NMR (CDCl 3 ) δ 117.3, (2 C, d, J = 5 Hz), (2 C), 130.7, 134.0, (1 C, d, J = 70 Hz), (1 C, d, J = 74 Hz); IR (KBr) 1678 cm -1 ; EIMS m/z (rel int) 149 (78, M + ); HREIMS m/z calcd for 12 C 8 13 CH 7 O 2 : , found: General Procedure for the Preparation of acryloyl azides 4. To a stirred solution of acrylic acid 3a-d, 3j or 3k (10 mmol) in CH 2 Cl 2 (50 ml) at room temperature was added oxalyl chloride (2.54 g, 20 mmol), and the mixture was stirred at room temperature for 5h. The resulting mixture concentrated under reduced pressure to afford acryloyl chloride quantitatively which was used S2
3 directly without further purification in the following reaction. The acryloyl chloride was added immediately into a suspension of NaN 3 (1.95 g, 30 mmol) in dry acetone (20 ml) on an ice bath. The reaction mixture was stirred gently for 2h at room temperature and filtered. The solvent was evaporated in vacuo, and the residue was purified by column chromatography over silica gel eluting with hexane-etoac (30:1) to yield pure acryloyl azide 4a-d 2, 4j or 4k. A mixture of acrylic acid 3e-g or 3i and oxalyl chloride in toluene was heated at 80 o C for 5h. Subsequently, a similar procedure as described above was used to prepare acryloyl azide 4e-g 2 or 4i. In the case of 4h, the mixture of acrylic acid 3h and oxalyl chloride in DMF was heated at 80 o C for 5h. After cooling, NaN 3 was added directly to the above solution, and the reaction mixture was stirred gently for 2h at room temperature to obtain acryloyl azide 4h. The full spectral data of 4a and 4h-k were described as follows. (E)-Cinnamoyl azide (4a). Yield 97%; white solid. 1 H NMR (300MHz, CDCl 3 ) δ 6.43 (1H, d, J = 16.0 Hz), 7.39 (3H, m), 7.53 (2H, m), 7.75 (1H, d, J = 16.0 Hz); 13 C NMR (75MHz, CDCl 3 ) δ 119.1, 128.5, 129.0, 131.1, 133.8, 146.7, 172.1; IR (KBr) 2146, 1687 cm -1 ; EIMS m/z (rel int) 173 (43, M + ); HREIMS m/z calcd for C 9 H 7 N 3 O: , found: [M] +. (E)-[2-13 C]Cinnamoyl azide (4a- 13 C). Yield 93%; white solid. 1 H NMR (300MHz, CDCl 3 ) δ 6.42 (1H, dd, J = 163.1, 15.9 Hz), 7.41 (3H, m), 7.53 (2H, m), 7.75 (1H, dd, J = 15.9, 2.9 Hz); 13 C NMR (75MHz, CDCl 3 ) δ 119.0, (2 C, d, J = 5 Hz), (2 C), 131.1, 133.8, (1 S3
4 C, d, J = 70 Hz), (1 C, d, J = 73 Hz); IR (KBr) 2149, 1678 cm -1 ; FABMS m/z (rel int) 174 (36, M + ); HRFABMS m/z calcd for 12 C 8 13 CH 7 N 3 O: , found: [M] +. (E)-3-(3-Pyridyl)acryloyl azide (4h). Yield 90%; pale yellow solid. 1 H NMR (300MHz, CDCl 3 ) δ 6.50 (1H, d, J = 16.0 Hz), 7.36 (1H, dd, J = 8.0, 4.8 Hz), 7.75 (1H, d, J = 16.0 Hz), 7.86 (1H, dt, J = 8.0, 1.6 Hz), 8.65 (1H, dd, J = 4.8, 1.6 Hz), 8.76 (1H, d, J = 1.6 Hz); 13 C NMR (75MHz, CDCl 3 ) δ 121.1, 123.8, 129.6, 134.5, 142.8, 150.1, 151.7, 171.5; IR (KBr) 2149, 1680 cm -1 ; FABMS m/z (rel int) 175 (69, [MH] + ); HRFABMS m/z calcd for C 8 H 7 N 4 O: , found: [MH] +. (E)-3-(Ethoxycarbonyl)acryloyl azide (4i). Yield 60%; colorless liquid. 1 H NMR (300MHz, CDCl 3 ) δ 1.33 (3H, t, J = 7.1 Hz), 4.28 (2H, q, J = 7.1 Hz), 6.80 (1H, d, J = 15.8 Hz), 6.90 (1H, d, J = 15.8 Hz); 13 C NMR (75MHz, CDCl 3 ) δ 13.9, 61.5, 133.7, 134.8, 164.3, 170.7; IR (KBr) 2964, 2140, 1698, 1644 cm -1 ; FABMS m/z (rel int) 170 (12, [MH] + ); HRFABMS m/z calcd for C 6 H 8 N 3 O 3 : , found: [MH] +. (E)-2-Hexenoyl azide (4j). Yield 88%; colorless liquid. 1 H NMR (300MHz, CDCl 3 ) δ 0.94 (3H, t, J = 7.4 Hz), 1.50 (2H, sextet, J = 7.4 Hz), 2.22 (2H, q, J = 7.4 Hz), 5.86 (1H, d, J = 15.5 Hz), 7.07 (1H, dt, J = 15.5, 7.4 Hz); 13 C NMR (75MHz, CDCl 3 ) δ 13.5, 21.0, 34.4, 122.7, 152.1, 171.7; IR (KBr) 2141, 1699 cm -1 ; EIMS m/z (rel int) 111 (10, [M-N 2 ] + ); HREIMS m/z calcd for C 6 H 9 NO: , found: [M-N 2 ] +. (E)-3-Butoxyacryloyl azide (4k). Yield 87%; colorless liquid. 1 H NMR (300MHz, CDCl 3 ) δ 0.95 (3H, t, J = 7.4 Hz), 1.42 (2H, sextet, J = 7.4 Hz), 1.70 (2H, quintet, J = 7.4 Hz), 3.90 (2H, t, J = 7.4 Hz), 5.23 (1H, d, J = 12.4 Hz), 7.68 (1H, d, J = 12.4 Hz); 13 C NMR (75MHz, CDCl 3 ) δ 13.6, S4
5 18.9, 30.8, 71.7, 98.4, 164.7, 172.2; IR (KBr) 2141, 1690 cm -1 ; FABMS m/z (rel int) 170 (7, [MH] + ); HRFABMS m/z calcd for C 7 H 12 N 3 O 2 : , found: [MH] +. References 1. Hano, Y.; Shimazaki, M.; Nomura, T.; Ueda, S. Heterocycles 1999, 50, Chuang, T. H.; Wu, P. L. J. Chin. Chem. Soc. 2006, 53, S5
6 O 13 C OH 3a- 13 C 1 H NMR (300MHz, CDCl 3) S6
7 O 13 C OH 3a- 13 C 13 C NMR (75MHz, CDCl 3) S7
8 N 3 O 4a 1 H NMR (300MHz, CDCl 3) S8
9 N 3 O 4a 13 C NMR (75MHz, CDCl 3) S9
10 O 13 C N 3 4a- 13 C 1 H NMR (300MHz, CDCl 3) S10
11 O 13 C N 3 4a- 13 C 13 C NMR (75MHz, CDCl 3) S11
12 N 3 O 4h N 1 H NMR (300MHz, CDCl 3) S12
13 N 3 O 4h N 13 C NMR (75MHz, CDCl 3) S13
14 O EtO 2 C N 3 4i 1 H NMR (300MHz, CDCl 3) S14
15 O EtO 2 C N 3 4i 13 C NMR (75MHz, CDCl 3) S15
16 N 3 O 4j 1 H NMR (300MHz, CDCl 3) S16
17 N 3 O 4j 13 C NMR (75MHz, CDCl 3) S17
18 O O N 3 4k 1 H NMR (300MHz, CDCl 3) S18
19 O O N 3 4k 13 C NMR (75MHz, CDCl 3) S19
20 N 5a 1 H NMR (300MHz, CDCl 3) S20
21 N 5a 13 C NMR (75MHz, CDCl 3) S21
22 13 C 13 C N 13 C 5a- 13 C 1 H NMR (300MHz, CDCl 3) S22
23 13 C 13 C N 13 C 5a- 13 C 13 C NMR (75MHz, CDCl 3) S23
24 OCH 3 N 5b H 3 CO 1 H NMR (300MHz, CDCl 3) S24
25 OCH 3 N 5b H 3 CO 13 C NMR (75MHz, CDCl 3) S25
26 OCH 3 N 5c H 3 CO 1 H NMR (300MHz, CDCl 3) S26
27 OCH 3 N 5c H 3 CO 13 C NMR (75MHz, CDCl 3) S27
28 OCH OCH 3 3 N 5d 1 H NMR (300MHz, CDCl 3) S28
29 OCH OCH 3 3 N 5d 13 C NMR (75MHz, CDCl 3) S29
30 NO 2 N 5e O 2 N 1 H NMR (300MHz, DNSO-d 6) S30
31 NO 2 N 5e O 2 N 13 C NMR (75MHz, DMSO-d 6) S31
32 NO 2 N 5f O 2 N 1 H NMR (300MHz, CDCl 3) S32
33 NO 2 N 5f O 2 N 13 C NMR (75MHz, CDCl 3) S33
34 NO NO 2 2 N 5g 1 H NMR (300MHz, CDCl 3) S34
35 NO NO 2 2 N 5g 13 C NMR (75MHz, CDCl 3) S35
36 N N 5h N 1 H NMR (300MHz, CDCl 3) S36
37 N N 5h N 13 C NMR (75MHz, CDCl 3) S37
38 EtO 2 C CO 2 Et N 5i 1 H NMR (300MHz, CDCl 3) S38
39 EtO 2 C CO 2 Et N 5i 13 C NMR (75MHz, CDCl 3) S39
40 N 5j 1 H NMR (300MHz, CDCl 3) S40
41 N 5j 13 C NMR (75MHz, CDCl 3) S41
42 N 6a 1 H NMR (300MHz, CDCl 3) S42
43 N 6a 13 C NMR (75MHz, CDCl 3) S43
44 13 C 13 C N 13 C 6a- 13 C 1 H NMR (400MHz, CDCl 3) S44
45 S45
46 13 C 13 C N 13 C 6a- 13 C 13 C NMR (100MHz, CDCl 3) S46
47 OCH 3 OCH 3 N 6b H 3 CO 1 H NMR (300MHz, CDCl 3) S47
48 OCH 3 OCH 3 N 6b H 3 CO 13 C NMR (75MHz, CDCl 3) S48
49 OCH 3 OCH 3 N 6c H 3 CO 1 H NMR (300MHz, CDCl 3) S49
50 OCH 3 OCH 3 N 6c H 3 CO 13 C NMR (75MHz, CDCl 3) S50
51 OCH OCH 3 3 N OCH 3 6d 1 H NMR (300MHz, CDCl 3) S51
52 OCH OCH 3 3 N OCH 3 6d 13 C NMR (75MHz, CDCl 3) S52
53 N 6j 1 H NMR (300MHz, CDCl 3) S53
54 N 6j 13 C NMR (75MHz, CDCl 3) S54
55 O N 7 O 1 H NMR (300MHz, CDCl 3) S55
56 O N 7 O 13 C NMR (75MHz, CDCl 3) S56
57 1 H NMR (300MHz, CDCl 3) H N O NH 8a S57
58 13 C NMR (75MHz, CDCl 3) H N O NH 8a S58
59 1 H NMR (400MHz, DMSO-d 6) H N O 9a S59
60 13 C NMR (100MHz, DMSO-d 6) H N O 9a S60
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