Supporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of. 1,2,3-Triazole Synthesis
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1 Supporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of α-diazoketones with Various Amines: A Strategy for Catalytic Wolff 1,2,3-Triazole Synthesis Zikun Wang, a Xihe Bi, b,c* Peiqiu Liao, b Rui Zhang, a Yongjiu Liang, a Dewen Dong a,b* a Changchun Institute of Applied Chemistry, Chinese Academy of Science, Changchun , P.R. of China. b Department of Chemistry, Northeast Normal University, Changchun , China. c State Key Laboratory and Institute of Elemento-organic Chemistry, Tianjin , China. bixh507@nenu.edu.cn; dwdong@ciac.jl.cn Contents Table of contents S1 I. General Information S2 II. Synthesis and analytical data for α-diazo-β-oxoamides and 1,2,3-trizaoles - S2-S19 III. Single-crystal X-ray diffraction data for compound 2a S19-S20 IV. 1 H- and 13 C-NMR Spectra Copies S21-S74 S1
2 I. General Information All reagents were purchased from commercial sources and used without treatment, unless otherwise indicated. The products were purified by column chromatography over silica gel. 1 H NMR and 13 C NMR spectra were recorded at 25 C at 300MHz or 400MHz or 500 MHz and 100MHz or 125 MHz, respectively, with TMS as internal standard. Mass spectra were recorded on BRUKER AutoflexIII Smartbeam MS-spectrometer. High resolution mass spectra (HRMS) were recorded on Bruck microtof by using ESI method. II. Synthesis and analytical data for α-diazo-β-oxoamides and 1,2,3-trizaoles. Synthesis of α-diazo-1,3-dicarbonyl compounds (with 1a as an example): To a solution of 3-oxo-N-phenylbutanamide (30 mmol) and triethylamine (60 mmol) in 50 ml of acetonitrile was added tosyl azide (33 mmol). The solution was stirred for 12 h at room temperature until the 3-oxo-N-phenylbutanamide disappeared (monitored by TLC). The reaction mixture was then treated with 250 ml brine, and extracted with dichloromethane (2 100 ml). The combined organic layer was washed with brine (3 100 ml), dried over MgSO 4 and filtered. The filtrate was concentrated in vacuum, and purified by silica gel column chromatography to give 1a as a yellowish solid. 2-diazo-3-oxo-N-phenylbutanamide (1a) Yellowish solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ (s, 1H), (m, 2H), (m, 2H), (m, 1H), 2.42 (s, 3H). 13 C-NMR (CDCl 3, 125Hz) δ 189.8, 158.0, 137.8, 128.9, 124.3, 119.9, 78.3, HRMS Calcd for C 10 H 10 N 3 O 2 ([M + H] + ) ; Found diazo-3-oxo-N-(o-tolyl)butanamide (1b) Yellow solid; mp C. 1 H-NMR (CDCl 3, 500 MHz) δ (s, 1H), 8.12 (d, J = 10.0Hz, 1H), (m, 2H), (m, 1H), 2.40 (s, 3H), 2.35 (s, 3H). 13 C-NMR (CDCl 3, 125Hz) δ 190.0, 158.0, 136.3, 130.3, 127.7, 126.6, 124.4, 121.2, 78.5, 26.6, HRMS Calcd for C 11 H 12 N 3 O 2 ([M + H] + ) ; Found S2
3 diazo-3-oxo-N-(p-tolyl)butanamide (1c) Yellow solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ (s, 1H), (m, 2H), (m, 2H), 2.41 (s, 3H), 2.32 (s, 3H). 13 C-NMR (CDCl 3, 125Hz) δ 189.8, 157.8, 135.2, 133.9, 129.4, 119.9, 78.2, 26.6, HRMS Calcd for C 11 H 12 N 3 O 2 ([M + H] + ) ; Found diazo-N-(2-methoxyphenyl)-3-oxobutanamide (1d) Yellow solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ (s, 1H), (m, 1H), (m, 1H), (m, 2H), 3.94 (s, 3H), 2.41 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 189.5, 157.8, 148.5, 127.9, 124.0, 120.8, 120.0, 110.1, 78.4, 55.8, HRMS Calcd for C 11 H 12 N 3 O 3 ([M + H] + ) ; Found diazo-N-(4-methoxyphenyl)-3-oxobutanamide (1e) Yellow solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ (s, 1H), (m, 2H), (m, 2H), 3.79 (s, 3H), 2.41 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 189.7, 157.6, 156.1, 130.9, 121.3, 113.8, 77.9, 55.2, HRMS Calcd for C 11 H 12 N 3 O 3 ([M + H] + ) ; Found N-(2-chlorophenyl)-2-diazo-3-oxobutanamide S3
4 (1f) Yellow solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ (s, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 1H), 2.43 (s, 3H). 13 C-NMR (CDCl 3, 125Hz) δ 189.5, 158.4, 135.0, 129.1, 127.4, 124.6, 123.2, 121.5, 78.5, HRMS Calcd for C 10 H 9 ClN 3 O 2 ([M + H] + ) ; Found N-(4-chlorophenyl)-2-diazo-3-oxobutanamide (1g) Yellow solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ (s, 1H), (m, 2H), (m, 2H), 2.41 (s, 3H). 13 C-NMR (CDCl 3, 125Hz) δ 189.8, 158.1, 136.4, 129.1, 128.9, 121.1, 78.2, HRMS Calcd for C 10 H 9 ClN 3 O 2 ([M + H] + ) ; Found diazo-N-(2,4-dimethylphenyl)-3-oxobutanamide (1h) Yellow solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ (s, 1H), (m, 1H), (m, 2H), 2.41 (s, 3H), 2.30 (s, 3H), 2.29 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 190.0, 157.8, 134.0, 133.7, 130.9, 127.7, 127.0, 121.3, 78.3, 26.5, 20.7, HRMS Calcd for C 12 H 14 N 3 O 2 ([M + H] + ) ; Found diazo-3-oxo-N-(4-(trifluoromethyl)phenyl)butanamide (1i) Yellow solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ (s, 1H), 7.72 (d, J = 9.0Hz, 2H), 7.58 (d, J = 9.0Hz, 2H), 2.44 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 189.9, 158.6, 140.8, 129.6, 126.2, 125.4, 122.7, 119.6, 78.4, HRMS Calcd for C 11 H 9 F 3 N 3 O 2 ([M + H] + ) ; Found S4
5 2-diazo-3-oxo-N-(pyridin-2-yl)butanamide (1j) Yellowish solid; mp C. 1 H-NMR (CDCl 3, 400 MHz) δ (s, 1H), (m, 1H), 8.14 (d, J = 8.4Hz, 1H), (m, 1H), (m, 1H), 2.41 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 188.9, 158.6, 151.0, 148.0, 138.0, 119.8, 114.0, 78.0, HRMS Calcd for C 9 H 8 N 4 NaO 2 ([M + Na] + ) ; Found diazo-3-oxo-N-phenylhexanamide (1k) Yellow solid; mp C. 1 H-NMR (CDCl 3, 400 MHz) δ (s, 1H), (m, 2H), (m, 2H), (m, 1H), 2.60 (t, J = 7.6Hz, 2H), (m, 2H), 1.02 (t, J = 7.6Hz, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 192.8, 158.3, 137.9, 128.9, 124.2, 119.8, 77.5, 40.8, 17.5, HRMS Calcd for C 12 H 14 N 3 O 2 ([M + H] + ) ; Found diazo-3-oxo-N,3-diphenylpropanamide (1l) Yellowish solid; mp C. 1 H-NMR (CDCl 3, 400 MHz) δ (s, 1H), (m, 5H), 7.53 (t, J = 8.0Hz, 2H), 7.36 (t, J = 8.0Hz, 2H), 7.14 (t, J = 8.0Hz, 1H). 13 C-NMR (CDCl 3, 100Hz) δ 187.9, 158.5, 137.8, 136.5, 132.7, 129.0, 127.0, 124.4, 120.0, HRMS Calcd for C 15 H 12 N 3 O 2 ([M + H] + ) ; Found diazo-5,5-dimethylcyclohexane-1,3-dione (S2) Yellowish solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 2.44 (s, 4H), 1.11 S5
6 (s, 6H). 13 C-NMR (CDCl 3, 100Hz) δ 189.7, 75.2, 50.4, 31.0, HRMS Calcd for C 8 H 11 N 2 O 2 ([M + H] + ) ; Found diazopiperidine-2,4-dione (S3) White solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 6.22 (s, 1H), 3.50 (t, J = 6.0Hz, 2H), 2.65 (t, J = 6.0Hz, 2H). 13 C-NMR (CDCl 3, 100Hz) δ 188.0, 163.5, 75.4, 36.9, HRMS Calcd for C 5 H 6 N 3 O 2 ([M + H] + ) ; Found diazo-N-methyl-3-oxo-N-phenylbutanamide (S4) Yellow oil; 1 H-NMR (CDCl3, 300 MHz) δ (m, 2H), (m, 1H), 7.20 (d, J = 6.0Hz, 2H), 3.38 (s, 3H), 2.50 (s, 3H). 13 C-NMR (CDCl3, 125Hz) δ 191.6, 160.6, 142.7, 130.0, 127.7, 126.0, 74.2, 38.2, HRMS Calcd for C 11 H 11 N 3 O 2 ([M + H] + ) ; Found Synthesis of 1,2,3-triazoles (with 2a1 as an example): To a solution of 1a (5 mmol) and aniline (5 mmol) in DMF (10 ml) was added 0.2 equiv of FeCl 2 (1 mmol). The mixture was warmed to 80 C and stirred for 10 h. When 1a disappeared (monitored by TLC), the reaction mixture was then treated with 50 ml brine, and extracted with dichloromethane (2 50 ml). The combined organic layer was washed with brine (3 50 ml), dried over MgSO 4 and filtered. The filtrate was concentrated in vacuum, and then purified by silica gel column chromatography to give 2a1 as a white solid. 5-methyl-N,1-diphenyl-1H-1,2,3-triazole-4-carboxamide S6
7 (2a1) White solid; mp C. 1 H-NMR (CDCl 3, 400 MHz) δ 9.07 (s, 1H), 7.72 (d, J = 8.0Hz, 2H), (m, 3H), (m, 2H), 7.39 (t, J = 8.0Hz, 2H), 7.16 (t, J = 7.6Hz, 1H), 2.69 (s, 3H). 13 C-NMR (CDCl 3, 125Hz) δ 159.2, 138.5, 137.6, 137.3, 135.4, 130.0, 129.6, 129.0, 125.2, 124.3, 119.7, 9.8. HRMS Calcd for C 16 H 15 N 4 O ([M + H] + ) ; Found methyl-1-phenyl-N-(o-tolyl)-1H-1,2,3-triazole-4-carboxamide (2a2) White solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.03 (s, 1H), 8.12 (d, J = 6.0Hz, 1H), (m, 3H), (m, 2H), (m, 2H), (m, 1H), 2.69 (s, 3H), 2.43 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.0, 138.6, 137.1, 135.5, 130.4, 129.9, 129.5, 128.3, 126.6, 125.1, 124.6, 121.8, 17.6, 9.6. HRMS Calcd for C 17 H 17 N 4 O ([M + H] + ) ; Found methyl-1-phenyl-N-(p-tolyl)-1H-1,2,3-triazole-4-carboxamide (2a3) White solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.02 (s, 1H), (m, 5H), (m, 2H), 7.19 (d, J = 8.1Hz, 2H), 2.68 (s, 3H), 2.35 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.0, 138.6, 137.2, 135.4, 135.1, 133.8, 129.9, 129.6, 129.5, 125.2, 119.7, 20.8, 9.7. HRMS Calcd for C 17 H 17 N 4 O ([M + H] + ) ; Found N-(2-methoxyphenyl)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carboxamide (2a4) Yellow solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.70 (s, 1H), (m, 1H), (m, 3H), (m, 2H), (m, 3H), 3.96 (s, 3H), 2.69 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.1, 148.4, 138.9, 137.1, 135.5, 129.9, 129.6, 127.4, 125.2, 123.8, 120.8, 119.6, 110.0, 55.7, 9.7. HRMS Calcd for S7
8 C 17 H 17 N 4 O 2 ([M + H] + ) ; Found N-(4-methoxyphenyl)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carboxamide (2a5) White solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 8.98 (s, 1H), (m, 5H), (m, 2H), (m, 2H), 3.82 (s, 3H), 2.68 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ , 156.4, 138.6, 137.1, 135.5, 130.8, 130.0, 129.6, 125.2, 121.5, 114.2, 55.4, 9.7. HRMS Calcd for C 17 H 17 N 4 O 2 ([M + H] + ) ; Found N-(2-chlorophenyl)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carboxamide (2a6) Yellow solid; mp C. 1 H-NMR (CDCl 3, 400 MHz) δ 9.68 (s, 1H), (m, 1H), (m, 3H), (m, 3H), (m, 1H), (m, 1H), 2.69 (s, 3H). 13 C-NMR (CDCl 3, 125Hz) δ 159.2, 138.4, 137.5, 135.4, 134.5, 130.0, 129.6, 129.2, 127.5, 125.2, 124.6, 123.3, 121.2, 9.8. HRMS Calcd for C 16 H 14 ClN 4 O ([M + H] + ) ; Found N-(4-chlorophenyl)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carboxamide (2a7) White solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.07 (s, 1H), (m, 2H), (m, 3H), (m, 2H), (m, 2H), 2.68 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.2, 138.4, 137.5, 136.3, 135.4, 130.2, 129.7, 129.3, 129.1, 125.2, 121.0, 9.8. HRMS Calcd for C 16 H 14 ClN 4 O ([M + H] + ) ; Found S8
9 N-(2,4-dimethylphenyl)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carboxamide (2a8) White solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 8.94 (s, 1H), 7.94 (d, J = 9.0Hz, 1H), (m, 3H), (m, 2H), (m, 2H), 2.68 (s, 3H), 2.38 (s, 3H), 2.32 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.2, 138.8, 137.1, 135.6, 134.5, 132.9, 131.2, 130.0, 129.7, 128.8, 127.2, 125.2, 122.3, 20.8, 17.7, 9.8. HRMS Calcd for C 18 H 19 N 4 O ([M + H] + ) ; Found methyl-1-phenyl-N-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazole-4-carboxamide (2a9) White solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.23 (s, 1H), 7.86 (d, J = 8.4 Hz, 2H), (m, 5H), (m, 2H), 2.70 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.4, 140.8, 138.2, 137.8, 135.3, 130.2, 129.7, , 126.3, 125.4, 125.2, 122.7, 119.3, 9.8. HRMS Calcd for C 17 H 14 F 3 N 4 O ([M + H] + ) ; Found methyl-1-phenyl-N-(pyridin-2-yl)-1H-1,2,3-triazole-4-carboxamide (2a10) White solid; mp C. 1 H-NMR (CDCl 3, 400 MHz) δ 9.69 (s, 1H), (m, 2H), (m, 1H), (m, 3H), (m, 2H), (m, 1H), 2.69 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.5, 151.1, 148.1, 138.1, 137.6, 135.4, 130.0, 129.6, 125.1, 119.7, 113.8, 109.5, 9.8. HRMS Calcd for C 15 H 14 N 5 O ([M + H] + ) ; Found N,1-diphenyl-5-propyl-1H-1,2,3-triazole-4-carboxamide S9
10 (2a11) Yellow solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.12 (s, 1H), 7.72 (d, J = 6.0 Hz, 2H), (m, 3H), (m, 2H), 7.39 (t, J = 6.0 Hz, 2H), 7.15 (t, J = 7.5 Hz, 1H), (m, 2H), (m, 2H), 0.88 (t, J = 7.5 Hz, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.0, 141.8, 138.2, 137.6, 135.7, 130.2, 129.6, 129.0, 125.7, 124.2, 119.8, 25.0, 22.2, HRMS Calcd for C 18 H 19 N 4 O ([M + H] + ) ; Found N,1,5-triphenyl-1H-1,2,3-triazole-4-carboxamide (2a12) Yellow solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.22 (s, 1H), 7.71 (d, J = 6.0 Hz, 2H), (m, 12H), 7.14 (t, J = 7.5Hz, 1H). 13 C-NMR (CDCl 3, 100Hz) δ 158.0, 139.5, 138.7, 137.6, 135.9, 131.7, 130.5, 129.9, 129.5, 129.3, 129.0, 128.3, 125.2, 124.3, HRMS Calcd for C 21 H 17 N 4 O ([M + H] + ) ; Found methyl-N-phenyl-1-(o-tolyl)-1H-1,2,3-triazole-4-carboxamide (2b1) White solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.10 (s, 1H), (m, 2H), (m, 5H), (m, 1H), (m, 1H), 2.50 (s, 3H), 2.07 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.2, 138.2, , 135.4, 134.2, 131.4, 130.7, 129.0, 127.1, 127.0, 124.2, 119.7, 17.1, 9.1. HRMS Calcd for C 17 H 17 N 4 O ([M + H] + ) ; Found (2-methoxyphenyl)-5-methyl-N-phenyl-1H-1,2,3-triazole-4-carboxamide (2b2) Yellow solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.10 (s, 1H), (m, 2H), (m, 1H), (m, 3H), (m, 3H), 3.83 (s, 3H), 2.52 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.3, 153.8, 139.3, 137.7, 132.0, S10
11 128.9, 128.3, 124.0, 123.9, 120.9, 119.6, 112.1, 55.7, 9.0. HRMS Calcd for C 17 H 17 N 4 O 2 ([M + H] + ) ; Found methyl-N-phenyl-1-(p-tolyl)-1H-1,2,3-triazole-4-carboxamide (2b3) Yellow solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.08 (s, 1H), (m, 2H), (m, 6H), (m, 1H), 2.66 (s, 3H), 2.48 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.2, 140.4, 138.4, 137.7, 137.3, 133.0, 130.2, 129.0, 125.0, 124.2, 119.7, 21.2, 9.7. HRMS Calcd for C 17 H 17 N 4 O ([M + H] + ) ; Found (4-methoxyphenyl)-5-methyl-N-phenyl-1H-1,2,3-triazole-4-carboxamide (2b4) White solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.08 (s, 1H), (m, 2H), (m, 4H), (m, 1H), (m, 2H), 3.90 (s, 3H), 2.65 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 160.7, 159.3, 138.4, 137.7, 137.5, 129.0, 128.3, 126.6, 124.2, 119.8, 114.8, 55.6, 9.7. HRMS Calcd for C 17 H 17 N 4 O 2 ([M + H] + ) ; Found (4-chlorophenyl)-5-methyl-N-phenyl-1H-1,2,3-triazole-4-carboxamide (2b5) White solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.05 (s, 1H), (m, 2H), (m, 2H), (m, 4H), (m, 1H), 2.69 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.0, 138.7, 137.5, 137.3, 136.2, 133.9, 129.9, 129.0, 126.4, 124.4, 119.8, 9.8. HRMS Calcd for C 16 H 14 ClN 4 O ([M + H] + ) ; Found S11
12 5-methyl-N-phenyl-1-(pyridin-2-yl)-1H-1,2,3-triazole-4-carboxamide (2b6) Yellow solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.10 (s, 1H), (m, 1H), (m, 2H), (m, 2H), (m, 3H), (m, 1H), 3.02 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.1, 150.0, 148.4, 139.0, 138.2, 137.5, 128.9, 128.8, 124.2, 124.0, 119.7, 118.0, HRMS Calcd for C 15 H 14 N 5 O ([M + H] + ) ; Found methyl-1-(naphthalen-1-yl)-N-phenyl-1H-1,2,3-triazole-4-carboxamide (2b7) Yellow solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.16 (s, 1H), 8.12 (d, J = 8.4 Hz, 1H), 8.01 (d, J = 8.4 Hz, 1H), 7.75 (d, J = 7.5 Hz, 2H), (m, 4H), 7.41 (t, J = 9.0 Hz, 2H), (m, 2H), 2.49 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.2, 139.4, 138.1, 137.7, 134.1, 131.5, 131.2, 129.3, 129.0, 128.4, 128.2, 127.3, 125.2, 125.0, 124.3, 121.8, 119.8, 9.2. HRMS Calcd for C 20 H 17 N 4 O ([M + H] + ) ; Found benzyl-5-methyl-N-phenyl-1H-1,2,3-triazole-4-carboxamide (2b8) Yellow solid; mp C. 1 H-NMR (CDCl 3, 500 MHz) δ 9.04 (s, 1H), (m, 2H), (m, 5H), (m, 2H), 7.13 (t, J = 7.5Hz, 1H), 5.52 (s, 2H), 2.54 (s, 3H). 13 C-NMR (CDCl 3, 125Hz) δ 159.2, 138.7, 137.6, 136.8, 133.8, 129.0, 129.0, 128.5, 127.1, 124.2, 119.7, 51.8, 8.8. HRMS Calcd for C 17 H 17 N 4 O ([M + H] + ) ; Found S12
13 5-methyl-N-phenyl-1-propyl-1H-1,2,3-triazole-4-carboxamide (2b9) White solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.02 (s, 1H), (m, 2H), (m, 2H), (m, 1H), 4.27 (t, J = 7.2Hz, 2H), 2.67 (s, 3H), (m, 2H), 1.00 (t, J = 7.5Hz, 3H). 13 C-NMR (CDCl 3, 125Hz) δ 159.3, 138.2, 137.6, 136.2, 129.0, 124.1, 119.6, 49.4, 23.1, 11.0, 8.7. HRMS Calcd for C 13 H 17 N 4 O ([M + H] + ) ; Found methyl-1-octadecyl-N-phenyl-1H-1,2,3-triazole-4-carboxamide (2b10) White solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.02 (s, 1H), 7.68 (d, J = 7.8Hz, 2H), 7.37 (t, J = 7.5Hz, 2H), 7.13 (t, J = 7.5Hz, 1H), 4.29 (t, J = 7.5Hz, 2H), 2.66 (s, 3H), (m, 32H), 0.87 (t, J = 6.0Hz, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.4, 138.4, 137.7, 136.2, 129.0, 124.2, 119.7, 48.0, 31.9, 29.6, 29.5, 29.3, 29.0, 26.5, 22.6, 14.1, 8.7. HRMS Calcd for C 28 H 46 N 4 O ([M + H] + ) ; Found cyclopropyl-5-methyl-N-phenyl-1H-1,2,3-triazole-4-carboxamide (2b11) White solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 8.98 (s, 1H), 7.68 (d, J = 8.4 Hz, 2H), 7.36 (t, J = 8.4 Hz, 2H), 7.13 (t, J = 7.2 Hz, 1H), (m, 1H), 2.74 (s, 3H), (m, 4H). 13 C-NMR (CDCl 3, 100Hz) δ 159.2, 138.5, 138.3, 137.6, 128.8, 124.0, 119.6, 29.0, 8.8, 6.3. HRMS Calcd for C 13 H 15 N 4 O ([M + H] + ) ; Found cyclohexyl-5-methyl-N-phenyl-1H-1,2,3-triazole-4-carboxamide S13
14 (2b12) White solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.03 (s, 1H), 7.68 (d, J = 8.4 Hz, 2H), 7.36 (t, J = 7.5 Hz, 2H), 7.13 (t, J = 7.5 Hz, 1H), (m, 1H), 2.67 (s, 3H), (m, 7H), (m, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.5, 138.0, 137.7, 135.5, 128.9, 124.0, 119.7, 58.1, 32.6, 25.4, 24.9, 8.6. HRMS Calcd for C 16 H 21 N 4 O ([M + H] + ) ; Found methyl 2-(5-methyl-4-(phenylcarbamoyl)-1H-1,2,3-triazol-1-yl)acetate (2b13) White solid; mp C. 1 H-NMR (CDCl 3, 400 MHz) δ 8.98 (s, 1H), (m, 2H), (m, 2H), (m, 1H), 5.11 (s, 2H), 3.81 (s, 3H), 2.62 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 166.0, 159.0, 138.6, 137.8, 137.5, 129.0, 124.3, 119.8, 53.1, 48.6, 8.6. HRMS Calcd for C 13 H 15 N 4 O 3 ([M + H] + ) ; Found tert-butyl (2-(5-methyl-4-(phenylcarbamoyl)-1H-1,2,3-triazol-1-yl)ethyl)carbamate (2b14) White solid; mp C. 1 H-NMR (CDCl 3, 500 MHz) δ 9.00 (s, 1H), (m, 2H), (m, 2H), (m, 1H), 4.84 (s, 1H), (m, 2H), (m, 2H), 2.65 (s, 3H), 1.43 (s, 9H). 13 C-NMR (CDCl 3, 100Hz) δ 159.2, 155.8, 138.4, 137.6, 137.4, 129.0, 124.3, 119.8, 80.2, 47.2, 40.3, 28.3, 8.6. HRMS Calcd for C 17 H 24 N 5 O 3 ([M + H] + ) ; Found (2-hydroxyethyl)-5-methyl-N-phenyl-1H-1,2,3-triazole-4-carboxamide (2b15) White solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 8.97 (s, 1H), (m, 2H), (m, 2H), 7.14 (t, J = 7.5Hz, 1H), (m, 2H), (m, 2H), (m, 4H). 13 C-NMR (CDCl 3, 100Hz) δ 159.2, 137.9, 137.7, 137.3, 128.9, 124.3, 119.9, 60.7, 50.1, 8.7. HRMS Calcd for C 12 H 15 N 4 O 2 ([M + H] + ) ; Found S14
15 1-allyl-5-methyl-N-phenyl-1H-1,2,3-triazole-4-carboxamide (2b16) White solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.01 (s, 1H), 7.69 (d, J = 7.8Hz, 2H), 7.37 (t, J = 7.8Hz, 2H), 7.14 (t, J = 7.5 Hz, 1H), (m, 1H), 5.35 (d, J = 10.2Hz, 1H), 5.11 (d, J = 17.1Hz, 1H), (m, 2H), 2.64 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.2, 138.5, 137.6, 136.7, 130.4, 128.9, 124.1, 119.7, 119.0, 50.3, 8.6. HRMS Calcd for C 13 H 15 N 4 O ([M + H] + ) ; Found methyl-N-phenyl-1-(prop-2-yn-1-yl)-1H-1,2,3-triazole-4-carboxamide (2b17) White solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 8.99 (s, 1H), 7.68 (d, J = 7.8Hz, 2H), 7.37 (t, J = 8.0 Hz, 2H), 7.14 (t, J = 7.5 Hz, 1H), 5.15 (d, J = 2.4Hz, 2H), 2.77 (s, 3H), 2.51 (t, J = 2.4Hz, 1H). 13 C-NMR (CDCl 3, 100Hz) δ 159.0, 138.8, 137.5, 137.0, 129.0, 124.3, 119.7, 75.3, 74.5, 37.9, 8.7. HRMS Calcd for C 13 H 13 N 4 O ([M + H] + ) ; Found (R)-5-methyl-N-phenyl-1-(1-phenylethyl)-1H-1,2,3-triazole-4-carboxamide (2b18) White solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.05 (s, 1H), 7.67 (d, J = 9.0 Hz, 2H), (m, 5H), (m, 3H), 5.58 (q, J = 7.0 Hz, 1H), 2.50 (s, 3H), 2.09 (d, J = 6.0 Hz, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.3, 139.7, 138.7, 137.6, 136.5, 129.0, 128.9, 128.3, 125.9, 124.1, 119.7, 58.8, 21.6, 8.7. HRMS Calcd for C 13 H 13 N 4 O ([M + H] + ) ; Found S15
16 5-methyl-1-(methylamino)-N-phenyl-1H-1,2,3-triazole-4-carboxamide (2b19) Yellowish solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 8.97 (s, 1H), 7.68 (d, J = 9.0 Hz, 2H), 7.37 (t, J = 9.0 Hz, 2H), 7.14 (t, J = 7.5 Hz, 1H), 3.05 (s, 3H), 2.63 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 159.0, 137.5, 137.0, 136.0, 128.9, 124.1, 119.7, 39.9, 8.2. HRMS Calcd for C 11 H 14 N 5 O ([M + H] + ) ; Found methoxy-5-methyl-N-phenyl-1H-1,2,3-triazole-4-carboxamide (2b20) Yellowish solid; mp C. 1 H-NMR (CDCl 3, 400 MHz) δ 8.93 (s, 1H), 7.67 (d, J = 8.0Hz, 2H), 7.37 (t, J = 8.0Hz, 2H), 7.14 (t, J = 7.5 Hz, 1H), 4.31 (s, 3H), 2.64 (s, 3H). 13 C-NMR (CDCl 3, 100Hz) δ 158.5, 137.3, 136.5, 130.7, 128.9, 124.2, 119.6, 67.3, 7.5. HRMS Calcd for C 11 H 13 N 4 O 2 ([M + H] + ) ; Found Synthesis of NH-1,2,3-triazoles 2c1-2c5 (with 2c1 as an example): To a solution of 1a (5 mmol) and ammonium acetate (7.5mmol) dissolved in 10 ml of DMF was added 0.2 equiv of FeCl 2. The mixture was warmed to 80 C and stirred for 5 h. When 1a had disappeared (TLC). The reaction mixture was treated with 50 ml brine, and then extracted with dichloromethane (2 50 ml). The combined organic layer was washed with brine (3 50 ml), dried over MgSO 4 and filtered. The filtrate was concentrated in vacuum, and then purified by silica gel column chromatography to give 2c1 as a white solid. 5-methyl-N-phenyl-1H-1,2,3-triazole-4-carboxamide (2c1) White solid; mp C. 1 H-NMR (DMSO, 500 MHz) δ (s, 1H), 7.83 (d, J = 10.0 Hz, 2H), 7.32 (t, J = 10.0 Hz, 2H), 7.07 (t, J = 7.5Hz, 1H), 2.52 (s, 3H). 13 C-NMR (DMSO, 125Hz) δ 159.9, 138.7, 137.6, 128.6, 123.6, 120.3, 120.1, 9.3. HRMS Calcd for C 10 H 11 N 4 O ([M + H] + ) ; Found S16
17 N-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide (2c2) White solid; mp C. 1 H-NMR (DMSO, 300 MHz) δ (s, 1H), (s, 1H), 7.73 (d, J = 9.0Hz, 2H), 6.90 (d, J = 9.0Hz, 2H), 3.73 (s, 3H), 2.51 (s, 3H). 13 C-NMR (DMSO, 100Hz) δ 159.6, 155.6, 137.8, 131.9, 122.0, 113.7, 55.2, 9.3. HRMS Calcd for C 11 H 13 N 4 O 2 ([M + H] + ) ; Found N-(2,4-dimethylphenyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide (2c3) White solid; mp C. 1 H-NMR (DMSO, 300 MHz) δ (s, 1H), 9.62 (s, 1H), 7.39 (d, J = 6.0 Hz, 1H), 7.06 (s, 1H), 7.00 (d, J = 6.0 Hz, 1H), 2.50 (s, 3H), 2.27 (s, 3H), 2.21 (s, 3H). 13 C-NMR (DMSO, 100Hz) δ 159.6, 134.4, 133.3, 131.7, 130.8, 129.3, 126.5, 125.6, 124.9, 20.5, 17.6, 9.1. HRMS Calcd for C 12 H 15 N 4 O ([M + H] + ) ; Found N-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide (2c4) White solid; mp C. 1 H-NMR (DMSO, 400 MHz) δ (s, 1H), (s, 1H), 7.86 (d, J = 8.8Hz, 2H), 7.33 (d, J = 8.8Hz, 2H), 2.50 (s, 3H). 13 C-NMR (DMSO, 100Hz) δ 159.9, 137.8, 137.5, 137.4, 128.4, 127.2, 121.8, 9.2. HRMS Calcd for C 10 H 10 ClN 4 O ([M + H] + ) ; Found N-phenyl-5-propyl-1H-1,2,3-triazole-4-carboxamide S17
18 (2c5) White solid; mp C. 1 H-NMR (DMSO, 500 MHz) δ (s, 1H), 7.84 (d, J = 10.0 Hz, 2H), 7.31 (t, J = 7.5 Hz, 2H), 7.07 (t, J = 7.5 Hz, 1H), 2.96 (t, J = 7.5 Hz, 2H), (m, 2H), 0.89 (t, J = 7.5 Hz, 3H). 13 C-NMR (DMSO, 125Hz) δ 159.8, 138.8, 129.3, 128.6, 125.7, 123.6, 120.3, 25.3, 21.8, HRMS Calcd for C 12 H 15 N 4 O ([M + H] + ) ; Found Synthesis of bis-triazoles 3a and 3b (with 3a as an example): To a solution of 1h (5 mmol) and 1,6-diaminohexane (2 mmol) dissolved in 10 ml of DMF was added 0.2 equiv of FeCl 2. The mixture was warmed to 80 C and stirred for 10 h. When 1h had disappeared (TLC). The reaction mixture was treated with 50 ml brine, and then extracted with dichloromethane (2 50 ml). The combined organic layer was washed with brine (3 50 ml), dried over MgSO 4 and filtered. The filtrate was concentrated in vacuum, and then purified by silica gel column chromatography to give 3a as a pale pink solid. 1,1'-(hexane-1,6-diyl)bis(N-(2,4-dimethylphenyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide) (3a) Pale pink; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 8.86 (s, 2H), 7.90 (d, J = 9.0 Hz, 2H), (m, 4H), 4.29 (t, J = 6.0 Hz, 4H), 2.65 (s, 6H), 2.34 (s, 6H), 2.31 (s, 6H), (m, 4H), (m, 4H). 13 C-NMR (CDCl 3, 100Hz) δ 159.2, 138.5, 135.9, 134.2, 132.8, 131.0, 128.5, 127.0, 122.0, 47.4, 29.2, 26.8, 20.7, 17.5, 8.6. HRMS Calcd for C 30 H 39 N 8 O 2 ([M + H] + ) ; Found S18
19 1,1'-(hexane-1,6-diyl)bis(N-phenyl-5-propyl-1H-1,2,3-triazole-4-carboxamide) (3b) Yellow solid; mp C. 1 H-NMR (CDCl 3, 300 MHz) δ 9.03 (s, 2H), 7.68 (d, J = 7.5 Hz, 4H), 7.36 (t, J = 7.8 Hz, 4H), 7.13 (t, J = 7.5 Hz, 2H), 4.28 (t, J = 7.2 Hz, 4H), (m, 4H), (m, 4H), (m, 4H), (m, 4H), 1.02 (t, J = 7.5Hz, 6H). 13 C-NMR (CDCl 3, 100Hz) δ 159.1, 140.4, 138.1, 137.6, 129.0, 124.1, 119.7, 47.6, 29.7, 26.0, 24.7, 22.3, HRMS Calcd for C 30 H 39 N 8 O 2 ([M + H] + ) ; Found III. Single-crystal X-ray diffraction data for compound 2a1 Single-crystal X-ray diffraction data for compound 2a1 was collected at room temperature on a Oxford Diffraction Gemini R Ultra diffractometer, the X-ray generator using Mo-Kα (λ = Å) radiation with a ω scan technique. the crystal structures were solved by direct method of SHELXS-97 and refined by full-matrix least-squares techniques using the SHELXL-97 program. 1 Non-hydrogen atoms were refined anisotropic, and hydrogen atoms of the ligands were refined as rigid groups. Basic information of crystal parameters and structure refinement are listed in Table (a) G. M. Sheldrick, SHELXS-97, Program for Solution of Crystal Structures, University of Göttingen, Germany, 1997; (b) G. M. Sheldrick, SHELXL-97, Program for Refinement of Crystal Structures, University of Göttingen, Germany, S19
20 Table 1. Crystal data and structure refinement of 2a1. Empirical formula C 33 H 28 N 2 SCl Formula weight Temperature Crystal system Space group Unit cell dimensions 293(2) K Orthorhombic Pna21 a = (10) Å b = (14) Å c =7.9778(6) Å alpha = deg. beta = deg. gamma = deg. Volume (3) Å 3 Z 4 Calculated density Mg/m 3 Absorption coefficient mm -1 F(000) 1092 Crystal size 0.34 x 0.19 x 0.14 mm Theta range for data collection 2.76 to deg. Reflections collected / unique / 4413 [R(int) = ] Data / restraints / parameters 4413 / 1 / 347 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = S20
21 IV. 1 H- and 13 C-NMR Spectra Copies S21
22 S22
23 S23
24 S24
25 S25
26 S26
27 S27
28 S28
29 S29
30 S30
31 S31
32 S32
33 S33
34 S34
35 S35
36 S36
37 S37
38 S38
39 S39
40 S40
41 S41
42 S42
43 S43
44 S44
45 S45
46 S46
47 S47
48 S48
49 S49
50 S50
51 S51
52 S52
53 S53
54 S54
55 S55
56 S56
57 S57
58 S58
59 S59
60 S60
61 S61
62 S62
63 S63
64 S64
65 S65
66 S66
67 S67
68 S68
69 S69
70 S70
71 S71
72 S72
73 S73
74 S74
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