NaHSO4•H2O as an efficient and eco-friendly catalyst for the one-pot multicomponent synthesis of β-acetamido ketones under mild and heterogeneous conditions

Asadollah Hassankhani; Malek Taher Maghsoodlou; Sayyed Mostafa Habibi-Khorassani; Hassan Hosseini-Mahdiabad; Ghasem Marandi

doi:10.3998/ark.5550190.0009.215

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NaHSO4•H2O as an efficient and eco-friendly catalyst for the one-pot multicomponent synthesis of β-acetamido ketones under mild and heterogeneous conditions

Asadollah Hassankhani; Malek Taher Maghsoodlou; Sayyed Mostafa Habibi-Khorassani; Hassan Hosseini-Mahdiabad; Ghasem Marandi

Volume 2008, Issue 2, pp. 134-140

DOI: http://dx.doi.org/10.3998/ark.5550190.0009.215

Paper ID: 08-2572MP

Received on 2007-06-11; Accepted on 2007-12-29; Published on 2008-01-27

Permissions: This work is licensed under a Creative Commons Attribution-NonCommercial 3.0 License. Please contact [email protected] to use this work in a way not covered by the license.

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General Papers ARKIVOC 2008 (ii) 134-140 ß-Acetamido-ß-(4-chlorophenyl)propiophenone (Table 1, entry 5). IR (KBr) .max/cm-1: 3291, 1689, 1652; 1H NMR (300 MHz; CDCl3; Me4Si) dH 2.14 (s, 3 H, CH3), 3.49 (dd, J = 7.1 and 13.9 Hz, 1 H, CH2), 3.82 (dd, J=7.1 and 14.5 Hz, 1 H, CH2), 5.56 (m, 1H, methyne H ), 7.25-7.58 (m, 7H, Ar-H), 7.83(br, 1H, NH), 7.91 (d, J =7.3 Hz, 2 H, Ar-H). ß-Acetamido-ß-(phenyl)-4-chloropropiophenone (Table 1, entry 6). IR (KBr) .max/cm-1: 3480, 1690, 1653; 1H NMR (300 MHz; CDCl3; Me4Si) dH 2.09 (s, 3H, CH3), 3.48 (dd, J = 6.2 and 17.4 Hz, 1 H, CH2), 3.80 (dd, J=5.8 and 17.4 Hz, 1 H, CH2), 5.56 (m, 1H, methyne H ), 7.16 7.40 (m, 7H, Ar-H), 7.82(d, J =8.6 Hz, 2H, Ar-H), 8.32 (br, d, J =7.5 Hz, 1H, NH). ß-Acetamido-ß-(4-chlorophenyl)-4-chloropropiophenone (Table 1, entry 7). IR (KBr) .max/cm-1: 3266, 1673, 1638; 1H NMR (300 MHz; CDCl3; Me4Si) dH 2.19 (s, 3 H, CH3), 3.50 (dd, J= 7.3 and 10.9 Hz, 1 H, CH2), 3.81 (dd, J= 7.3 and 10.9 Hz, 1 H, CH2), 5.56 (m, 1H, methyne H ), 7.21 (br, 1 H, NH), 7.28-7.47 (m, 6H, Ar-H), 7.85 (d, J= 8.2, 2H, Ar-H). ß-Acetamido-ß-(4-nitrophenyl)-4-chloropropiophenone (Table 1, entry 8). IR (KBr) .max/cm1: 3346, 1693, 1690; 1H NMR (300 MHz; CDCl3; Me4Si) dH 2.09 (s, 3 H, CH3), 3.48 (dd, J= 5.6 and 17.6 Hz, 1 H, CH2), 3.81 (dd, J = 4.9 and 17.6 Hz, 1 H, CH2), 5.66 (m, 1H, methyne H ), 6.94 (br, d, J=7.6 Hz, 1 H, NH), 7.45 (d, J =8.6 Hz, 2H, Ar-H), 7.52 (d, J =8.7 Hz, 2H, Ar-H), 7.85 (d, J =8.6 Hz, 2H, Ar-H), 8.18 (d, J =8.7 Hz, 2H, Ar-H). ß-Acetamido-ß-(phenyl)-4-methylpropiophenone (Table 1, entry 9). IR (KBr) .max/cm-1: 3276, 1684, 1651; 1H NMR (300 MHz; CDCl3; Me4Si) dH 2.13 (s, 3 H, CH3), 2.30 (s, 3 H, CH3), 3.52 (dd, J= 6.1 and 16.3 Hz, 1 H, CH2), 3.79 (dd, J=5.5 and 17.3 Hz, 1 H, CH2), 5.56(m, 1H, methyne H ), 7.12-7.27 (m, 5H, Ar-H), 7.40 (d, J =7.2 Hz, 2H, Ar-H), 7.78 (d, J =7.7 Hz, 2H, Ar-H), 8.65 (br, d, J =7.1 Hz, 1H, NH). ß-Acetamido-ß-(4-nitrophenyl)-4-methylpropiophenone (Table 1, entry 10). IR (KBr) .max/cm-1: 3346, 1663, 1609; 1H NMR (300 MHz; CDCl3; Me4Si) dH 2.10 (s, 3 H, CH3), 2.41 (s, 3 H, CH3), 3.48 (dd, J= 5.4 and 16.8 Hz, 1 H, CH2), 3.80 (dd, J= 4.9 and 17.7 Hz, 1 H, CH2), 5.65 (m, 1H, methyne H ), 7.26(m,3 H, NH, Ar-H), 7.53(d, J =8.7 Hz, 2H, Ar-H ), 7.79(d, J =8.2 Hz, 2H, Ar-H), 8.15(d, J =8.7 Hz, 2H, Ar-H). ß-Acetamido-ß-(3-Acetoxy-phenyl)-propiophenone (Table 1, entry 11). IR (KBr) .max/cm-1: 3280, 1767, 1685, 1655, 1610; 1H NMR (300 MHz; CDCl3; Me4Si) dH 2.05 (s, 3H, CH3), 2.31 (s, 3H, CH3), 3.47 (dd, J = 5.8 and 17.0 Hz, 1H, CH2), 3.79 (dd, J = 5.7 and 17.1 Hz, 1H, CH2), 5.60 (m, 1 H, methyne H), 6.80 (br, d, J = 8.5 Hz, 1H, NH), 6.99 (dd, J = 2.2 and 7.8 Hz, 1H, Ar-H), 7.10 (t, J = 2.1 Hz, 1H, Ar-H), 7.19 (d, J = 8.0 Hz, 1H, Ar-H), 7.32(t, J = 7.8 Hz, 1H, Ar-H), 7.46-7.48(m, 2H, Ar-H), 7.56-7.60(m, H, Ar-H), 7.90 (d, J = 7.6 Hz, 2H, Ar-H). Acknowledgements The authors are thankful to the Sistan & Balouchestan University Research Council for partial support of this work. ISSN 1551-7012 Page 138 ©ARKAT USA, Inc.

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