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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