Supporting Information for

Solid-supported sulfonic acid-containing catalysts efficiently promoted one-pot multi-component synthesis of β-acetamido carbonyl compounds

MOHAMMAD ALI ZOLFIGOL, a,* ARDESHIR KHAZAEI, a,* ABDOLKARIM ZARE, b MOHAMMAD MOKHLESI, a TAHEREH HEKMAT-ZADEH, b ALIREZA HASANINEJAD, c FATEMEH DERAKHSHAN-PANAH, a AHMAD REZA MOOSASVI-ZARE, a HASSAN KEYPOUR, a AHMAD ALI DEHGHANI-FIROUZABADI d and MARIA MERAJODDIN b

a Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran

b Chemistry Department, Payame Noor University, 19395-4697 Tehran, I.R. of Iran

c Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr 75169, Iran

d Department of Chemistry, Yazd University, Yazd 89195741, Iran

E-mail: Mohammad Ali Zolfigol*- ; Ardeshir Khazaei*- ;

*Corresponding author.

Selected spectral data of the products

Note: Compounds 8, 9, 10, 17, 20, 21, 22, 23, 25, 26 and 27 are new.

2.2a N-(3-(4-Methoxyphenyl)-3-oxo-1-phenylpropyl)acetamide (table 1, compound 7): IR (KBr): 1678, 3268 cm-1. 1H NMR (CDCl3): δ 2.00 (s, 3H), 3.38 (dd, J = 5.9, 16.5 Hz, 1H), 3.66 (dd, J = 5.4, 16.6 Hz, 1H), 3.85 (s, 3H), 5.54 (q, J = 7.5 Hz, 1H), 6.91 (d, J = 8.7 Hz, 2H), 7.21-7.35 (m, 6H), 7.88 (d, J = 9.0 Hz, 2H); 13C NMR (CDCl3): δ 23.3, 42.8, 50.1, 55.5, 113.8, 126.5, 127.3, 128.6, 129.7, 130.5, 141.1, 163.8, 169.6, 196.9. MS: m/z = 297 (M+). Anal. Calcd. for C18H19NO3: C, 72.71; H, 6.44; N, 4.71. Found: C, 72.55; H, 6.58; N, 4.59.

2.2b N-(1,3-Bis(4-methoxyphenyl)-3-oxopropyl)acetamide (table 1, compound 8): IR (KBr): 1678, 3273 cm-1. 1H NMR (CDCl3): δ 2.02 (s, 3H), 3.67 (s, 1H), 3.76 (s, 3H), 3.86 (s, 3H), 5.49 (s, 1H), 6.88 (q, J = 7.8 Hz, 5H), 7.26 (d, J = 8.3 Hz, 2H), 7.90 (d, J = 8.0 Hz, 2H); 13C NMR (CDCl3): δ 23.4, 42.8, 49.7, 55.2, 55.5, 113.8, 113.9, 127.7, 129.6, 130.5, 133.1, 158.7, 163.7, 169.6, 197.2. MS: m/z = 327 (M+). Anal. Calcd. for C19H21NO4: C, 69.71; H, 6.47; N, 4.28. Found: C, 69.58; H, 6.58; N, 4.36.

2.2c N-(3-(4-Methoxyphenyl)-1-(naphthalen-3-yl)-3-oxopropyl)acetamide (table 1, compound 9): IR (KBr): 1671, 3276 cm-1. 1H NMR (CDCl3): δ 2.03 (s, 3H), 3.43 (d, J = 6.6 Hz, 1H), 3.79 (s, 4H), 5.72 (s, 1H), 6.90 (q, J = 6.8 Hz, 2H), 7.42-7.53(m, 4H), 7.75-8.10 (m, 5H) 8.23 (s, 1H); 13C NMR (CDCl3): δ 22.6, 43.1, 50.6, 55.5, 113.8, 124.8, 125.4, 126.0, 127.6, 127.9, 128.5, 129.5, 130.5, 132.6, 133.2, 138.4, 163.7, 170.9, 196.4. MS: m/z = 347 (M+). Anal. Calcd. for C22H21NO3: C, 76.06; H, 6.09; N, 4.03. Found: C, 76.27; H, 6.19; N, 3.95.

2.2d N-(1-(Anthracen-10-yl)-3-(4-methoxyphenyl)-3-oxopropyl)acetamide (table 1, compound 10):IR (KBr): 1674, 3184, 3279 cm-1, 1H-NMR (CDCl3): δ 2.06 (s, 3H), 3.84(s, 1H), 4.14 (q, J = 7.012, 1H), 5.27 (s, 1H), 6.86 (d, J = 8.7, 2H), 7.13 (d, J = 6.3, 1H), 7.46 (t, J = 6.9, 2H), 7.56 (t, J = 8.4, 2H), 7.91 (d, J = 8.7, 2H), 8.05 (d, J = 5.4, 2H), 8.42 (s, 1H), 8.52 (s, 2H). 13C NMR (CDCl3): δ 23.2, 29.7, 46.1, 55.4, 59.5, 113.7, 124.2, 124.9, 125.4, 126.5, 128.8, 129.1, 129.3, 129.7, 130.5, 131.9, 142.6, 163.5, 195.2. MS: m/z = 397 (M+). Anal. Calcd. For C26H23NO3: C, 78.57; H, 5.83; N, 3.52, Found: C, 78.77; H, 5.94; N, 3.59.

2.2e N-(3-Oxo-1,3-dip-tolylpropyl)acetamide (table 1, compound 11): IR (KBr): 1680, 3257 cm-1, 1H-NMR (CDCl3): δ 1.93 (s, 3H), 2.27 (s, 3H), 2.37 (s, 3H), 3.36 (q, J = 6.2 Hz, 1H), 3.64 (q, J = 5.8 Hz, 1H), 5.55 (q, J = 7.1 Hz, 1H), 7.09 (d, J = 7.7 Hz, 2H), 7.22 (m, 2H), 7.41 (d, J = 7.7 Hz, 1H), 7.80 (d, J = 7.7 Hz, 2H). 13C NMR (CDCl3): δ 21.1, 21.7, 23.1, 43.6, 49.8, 126.5, 128.3, 129.2, 129.3, 134.1, 136.9, 138.4, 144.2, 169.8, 197.8. MS: m/z = 295 (M+). Anal. Calcd. For C19H21NO2: C, 77.26; H, 7.17; N, 4.74; Found: C, 77.05; H, 7.30; N, 4.85.

2.2f N-(1-(4-Chlorophenyl)-3-oxo-3-p-tolylpropyl)acetamide (table 1, compound 12): IR (KBr): 1689, 3302 cm-1, 1H NMR (CDCl3): δ 2.02 (s, 3H), 2.40 (s, 3H), 3.35 (dd, J = 3.8, 17.1 Hz, 1H), 3.68 (dd, J = 5.3, 17.1 Hz, 1H), 5.5 (q, J = 5.5 Hz, 1H), 7.26 (m, 5H), 7.37 (s, 1H), 7.77 (d, J = 8.0 Hz, 3H); 13C NMR (CDCl3): δ 21.7, 23.1, 42.8, 49.3, 127.9, 128.2, 128.7, 129.4, 133.1, 133.8, 139.6, 144.7, 170.1, 197.8. MS: m/z = 312 (M+). Anal. Calcd. For C18H18ClNO2: C, 68.46; H, 5.75; N, 4.44; Found: C, 68.65; H, 5.90; N, 4.35.

2.2g N-(1-(Naphthalen-3-yl)-3-oxo-3-p-tolylpropyl)acetamide (table 1, compound 13): IR (KBr): 1676, 3280 cm-1, 1H-NMR (CDCl3): δ 1.96 (s, 3H), 2.39 (s, 3H), 3.46 (q, J = 8.7 Hz, 1H), 3.78 (q, J = 5.1 Hz, 1H), 5.73 (d, J = 6.8 Hz, 1H), 7.16-7.28 (m, 2H), 7.43-7.49 (m, 4H), 7.72-7.78 (m, 6H). 13C NMR (CDCl3): δ 21.7, 23.4, 43.1, 50.1, 124.7, 125.2, 125.9, 126.2, 127.9, 128.2, 128.4, 129.4, 129.6, 132.6, 133.2, 134.1, 138.4, 144.5, 169.7, 198.1. MS: m/z = 331 (M+). Anal. Calcd. For C22H21NO2: C, 79.73; H, 6.39; N, 4.23; Found: C, 79.55; H, 6.50; N, 4.35.

2.2h N-(3-(4-Nitrophenyl)-3-oxo-1-phenylpropyl)acetamide (table 1, compound 14): IR (KBr): 1689, 3302 cm-1, 1H NMR (CDCl3): δ 1.95 (s, 3H), 3.43 (dd, J = 3.5, 16.6 Hz, 1H), 3.78 (dd, J = 3.5, 14.1 Hz, 1H), 5.53 (q, J = 3.9 Hz, 1H), 6.95 (d, J = 6.3 Hz, 1H), 7.31 (s, 5H), 8.03 (d, J = 6.0 Hz, 2H), 8.23 (d, J = 5.8 Hz, 2H); 13C NMR (CDCl3): δ 23.1, 44.3, 50.1, 123.8, 126.5, 127.8, 129.2, 140.9, 150.3, 169.9, 196.6. MS: m/z = 312 (M+). Anal. Calcd. For C17H16N2O4: C, 65.38; H, 5.16; N, 8.97; Found: C, 65.57; H, 5.06; N, 8.84.

2.2i N-(1,3-Bis(4-nitrophenyl)-3-oxopropyl)acetamide (table 1, compound 15): IR (KBr): 1694, 3277 cm-1, 1H NMR (CDCl3): δ 2.10 (s, 3H), 3.61 (dd, J = 3.5, 14.1 Hz, 1H), 3.88 (dd, J = 3.8, 13.3 Hz, 1H), 5.69 (s, 1H), 6.73 (s, 1H), 7.27 (s, 1H),7.54 (s, 1H), 8.09-8.32 (m, 5H); 13C NMR (CDCl3): δ 29.7, 49.1, 59.5, 124.1, 124.1, 124.4, 129.2, 140.3, 147.3, 147.7, 150.7, 169.8, 196.3. MS: m/z = 357 (M+). Anal. Calcd. For C17H15N3O6: C, 57.14; H, 4.23; N, 11.76; Found: C, 57.36; H, 4.11; N, 11.64.

2.2j N-(1-(4-Chlorophenyl)-3-(4-nitrophenyl)-3-oxopropyl)acetamide (table 1, compound 16): IR (KBr): 1695, 3280 cm-1, 1H-NMR (CDCl3): δ 1.99 (s, 3H), 3.46 (q, J = 6.9 Hz, 1H), 3.84 (s, 1H), 5.52 (s, 1H), 7.11-7.27 (m, 3H), 7.73-7.78 (m, 1H), 8.05-8.31 (m, 5H). 13C NMR (CDCl3): δ 21.1, 22.7, 44.2, 44.4, 49.5, 50.1, 123.9, 126.5, 128.2, 128.9, 129.2, 129.5, 133.5, 137.1, 137.7, 140.8, 150.3, 170.7, 196.1. MS: m/z = 347 (M+). Anal. Calcd. For C17H15ClN2O4: C, 58.88; H, 4.36; N, 8.08; Found: C, 59.02; H, 4.27; N, 8.18.

2.2k N-(1-(Naphthalen-3-yl)-3-(4-nitrophenyl)-3-oxopropyl)acetamide (table 1, compound 17): IR (KBr): 1665, 3280 cm-1, 1H NMR (CDCl3): δ 2.08 (s, 3H), 2.85-3.05 (m, 2H), 5.50 (s, 1H), 7.47-8.5 (m, 12H); 13C NMR (CDCl3): δ 29.7, 49.8, 59.5, 124.7, 125.5, 126.4, 126.6, 126.8, 127.1, 127.5, 127.7, 128.1, 129.1, 129.4, 129.5, 130.5, 173.9, 194.1. MS: m/z = 362 (M+). Anal. Calcd. For C21H18N2O4: C, 69.60; H, 5.01; N, 7.73, Found: C, 69.49; H, 5.12; N, 7.69.

2.2l N-(3-(4-Bromophenyl)-3-oxo-1-phenylpropyl)acetamide (table 1, compound 18): IR (KBr): 1685, 3275 cm-1, 1H-NMR (CDCl3): δ 2.04 (s, 3H), 3.37 (q, J = 5.4 Hz, 1H), 3.66 (q, J = 5.4 Hz, 1H), 5.54 (q, J = 6.6 Hz, 1H), 6.99-7.75 (m, 9H). 13C NMR (CDCl3): δ 23.2, 29.6, 43.5, 50.0, 126.5, 127.5, 128.6, 129.6, 131.9, 135.3, 140.8, 169.7, 197.2. MS: m/z = 345 (M+). Anal. Calcd. For C17H16BrNO2: C, 58.97; H, 4.66; N, 4.05; Found: C, 58.81; H, 4.58; N, 4.14.

2.2m N-(3-(4-Bromophenyl)-1-(4-nitrophenyl)-3-oxopropyl)acetamide (table 1, compound 19): IR (KBr): 1687, 3261 cm-1, 1H-NMR (CDCl3): δ 2.05 (s, 3H), 3.47 (q, J = 5.6 Hz, 1H), 3.79 (q, J = 5.19 Hz, 1H), 5.65 (q, J = 5.5 Hz, 1H), 7.02 (d, J = 7.86 Hz, 1H), 7.58 (d, J = 8.7 Hz, 2H), 7.61 (d, J = 8.4 Hz, 2H), 7.76 (d, J = 8.4 Hz, 2H), 8.15 (d, J = 8.4 Hz, 2H). 13C NMR (CDCl3): δ 23.3, 42.7, 49.1, 113.8, 123.8, 127.4, 129.3, 129.5, 132.2, 134.8, 147.1, 148.4, 169.8, 196.8. MS: m/z = 390 (M+). Anal. Calcd. For C17H15BrN2O4: C, 52.19; H, 3.86; N, 7.16; Found: C, 52.35; H, 4.05; N, 7.05.

2.2n Compound 20 (table 1): IR (KBr): 1689, 1736, 3286 cm-1, 1H NMR (CDCl3): δ 2.07 (s, 3H), 3.46 (d, J = 6.8 Hz, 1H), 3.81 (d, J = 7.8 Hz, 1H), 5.63 (s, 1H), 7.09 (s, 1H), 7.2-7.6 (m, 3H), 7.7-8.2 (m, 4H), 9.96 (s, 1H); 13C NMR (CDCl3): δ 23.3, 42.8, 49.5, 127.1, 129.2, 129.6, 130.1, 132.1, 134.9, 135.5, 147.6, 170.01, 191.8, 197.1. MS: m/z = 373 (M+). Anal. Calcd. For C18H16BrNO3: C, 57.77; H, 4.31; N, 3.74. Found: C, 57.93; H, 4.42; N, 3.19.

2.2o N-(3-(4-Bromophenyl)-1-(naphthalen-3-yl)-3-oxopropyl)acetamide (table 1, compound 21): IR (KBr): 1682, 3276 cm-1, 1H NMR (CDCl3): δ 1.98 (s, 3H), 3.41 (dd, J = 6.4, 12.7 Hz, 1H), 3.76 (dd, J = 6.6, 13.2 Hz, 1H), 5.70 (s, 1H), 7.27-7.59 (m, 6H), 7.69-7.92 (m, 6H); 13C NMR (CDCl3): δ 23.2, 43.5, 50.1, 124.7, 125.3, 126.1, 126.3, 127.6, 128.6, 129.6, 131.9, 132.7, 133.1, 135.1, 138.2, 170.1, 197.1. MS: m/z = 395 (M+). Anal. Calcd. for C21H18BrNO2: C, 63.65; H, 4.58; N, 3.53, Found: C, 63.48; H, 4.67; N, 3.44.

2.2p N-(3-(4-aminophenyl)-1-(naphthalen-3-yl)-3-oxopropyl)acetamide (table 1, compound 22):IR (KBr): 1674, 3184, 3279 cm-1, 1H-NMR (CDCl3): δ 1.29 (s, 3H), 2.06 (s, 3H), 3.84 (s, 1H), 4.14 (q, J = 7.01, 1H), 5.23 (s, 1H), 5.75 (s, 2H), 7.41-7.98 (m, 12H). 13C NMR (CDCl3): δ 26.5, 29.7, 42.1, 60.5, 118.8, 119.1, 123.6, 126.1, 127.8, 127.9, 128.6, 129.7, 132.6, 133.1, 142.6, 144.7, 170.1, 189.2. MS: m/z = 347 (M+). Anal. Calcd. For C23H22N2O3: C, 73.78; H, 5.92; N, 7.48; Found: C, 73.94; H, 6.04; N, 7.39.

2.2q N-(3-(4-aminophenyl)-1-(anthracen-10-yl)-3-oxopropyl)acetamide (table 1, e compound 23):IR (KBr): 1674, 3184, 3279 cm-1, 1H-NMR (CDCl3): δ 1.88 (s, 3H), 2.00 (s, 3H), 3.75(q, J = 7.2, 1H), 3.94 (q, J = 8.4, 1H), 6.5 (s, 2H), 7.44-7.60 (m, 7H), 7.74-7.85 (m, 4H), 8.03 (d, J = 8.4, 2H). 13C NMR (CDCl3): δ 23.2, 24.5, 45.4, 58.4, 118.8, 124.1, 124.9, 126.5, 128.8, 129.4, 129.8, 131.7, 142.7, 170.2, 196.2. MS: m/z = 382 (M+). Anal. Calcd. for C27H24N2O3: C, 76.39; H, 5.70; N, 6.60, Found: C, 76.59; H, 5.61; N, 6.49.

2.2r Methyl 2-(acetamido(naphthalen-3-yl)methyl)-3-oxobutanoate (table 1, compound 25): IR (KBr): 1636, 1747, 3347 cm-1, 1H-NMR (CDCl3): δ 2.01 (s, 3H), 2.19 (s, 3H), 3.65 (s, 3H), 4.26 (s, 1H), 5.96 (s, 1H), 7.46 (m, 3H), 7.77 (m, 5H). 13C NMR (CDCl3): δ 23.3, 30.6, 52.6, 52.8, 62.7, 124.5, 125.7, 126.2, 127.6, 128.1, 128.6, 132.8, 133.1, 136.5, 167.6, 169.8, 203.5. MS: m/z = 313 (M+). Anal. Calcd. for C18H19NO4: C, 68.99; H, 6.11; N, 4.47, Found: C, 69.81; H, 6.23; N, 4.56.

2.2s Ethyl 2-(acetamido(naphthalen-3-yl)methyl)-3-oxobutanoate (table 1, compound 26): IR (KBr): 1647, 1720, 1746, 3332 cm-1, 1H-NMR (CDCl3): δ 1.11 (t, J = 5.0 Hz, 3H), 2.02 (s, 3H), 2.18 (s, 3H), 4.1 (q, J = 6.1 Hz, 2H), 4.17 (q, J = 6.3 Hz, 1H) 5.95 (s, 1H), 7.27 (m, 4H), 7.76 (t, J = 7.5 Hz, 4H). 13C NMR (CDCl3): δ 23.2, 30.6, 52.3, 52.8, 62.8, 126.6, 127.8, 128.7, 139.1, 167.6, 169.8, 203.6. MS: m/z = 327 (M+). Anal. Calcd. For C19H21NO4 C, 69.71; H, 6.47; N, 4.28. Found: C, 69.52; H, 6.34; N, 4.39.

2.2t Compound 27 (scheme 2): IR (KBr): 1674, 3433 cm-1, 1H NMR (CDCl3): δ 1.86 (s, 9H), 3.36-3.49 (m, 6H), 5.16 (s, 6H), 5.83 (s, 3H), 6.91-7.02 (m, 6H), 7.15-7.38 (m, 11H), 7.51-7.64 (m, 9H), 7.67-7.83 (m, 4H); 13C NMR (CDCl3): δ 23.0, 43.1, 46.8, 69.8, 112.3, 121.3, 126.2, 127.9, 128.4, 128.8, 129.7, 129.9, 131.8, 135.2, 138.1, 155.4, 168.2, 197.4 Anal. Calcd. For C60H54Br3N3O9: C, 60.01; H, 4.53; N, 3.50, Found: C, 59.88; H, 4.65; N, 3.42.

1