PAPER
Synthesis of N-Benzyl- or N-(2-Furylmethyl)cinnamamides
381
1-C/3-C/1¢-HPh], 4.71/177.0/136.7/129.3–126.3 [H-CH2/1-C/1¢¢-
CBn/C-Ar], 3.06/177.0 [H-Me/1-C].
(S*)-3-Phenyl-N-(1-phenylethyl)prop-2-enamide (3i)
[a]D26–80.9 (c 0.036, CHCl3).
GC-MS (EI, 70 eV): tR = 23.3 min; m/z (%) = 251 (48) [M+], 174
(24), 131 (100), 103 (90), 91 (37), 77(55).
13C NMR (100 MHz, CDCl3): d = 21.7 (+), 48.9 (+), 120.8 (+),
126.2 (+), 127.3 (+), 127.7 (+), 128.6 (+), 128.6 (+), 128.7 (+),
129.5 (+), 134.8, 141.1 (+), 143.1, 164.9.
N-(4-Fluorobenzyl)-3-phenylprop-2-enamide (3d)
GC-MS (EI, 70 eV): tR = 23.7 min; m/z (%) = 251 (35) [M+], 131
(100), 120 (50), 103 (52), 91 (4), 77 (48).
13C NMR (100 MHz, CDCl3): d = 43.1 (–), 115.5 (+), 115.5 (+),
115.7 (+), 120.3 (+), 127.8 (+), 128.8 (+), 129.5 (+), 129.6 (+),
129.8 (+), 134.1, 134.7 (+), 141.5 (+), 160.9, 163.4, 165.9.
N-(2-Furylmethyl)-3-phenylprop-2-enamide (3j)
13C NMR (100 MHz, CDCl3): d = 36.7 (+), 107.4 (+), 110.5 (+),
120.4 (+), 127.8 (+), 128.6 (+), 128.8 (+), 127.7 (+), 134.7, 141.4
(+), 142.2 (+), 151.1, 165.8.
GC-MS (EI, 70 eV): tR = 23.9 min; m/z (%) = 255 (50) [M+], 131
(100), 103 (58), 91 (3), 77 (47).
N-(4-Chlorobenzyl)-3-phenylprop-2-enamide (3e)
13C NMR (100 MHz, CDCl3): d = 43.1 (–), 120.1 (+), 127.8 (+),
128.8 (+), 129.2 (+), 129.8 (+), 133.4, 134.6, 136.8, 141.7 (+),
165.8.
GC-MS (EI, 70 eV): tR = 21.3 min; m/z (%) = 227 (53) [M+], 131
(100), 103 (95), 81 (23), 77 (92).
GC-MS (EI, 70 eV): tR = 26.1 min; m/z (%) = 271 (36) [M+], 140
(28), 131 (100), 103 (56), 77 (50).
Acknowledgment
This work was financially supported by a grant of the Colombian
Institute for Science and Research (COLCIENCIAS-CENIVAM,
contract no. 432-2004). LYVM thanks COLCIENCIAS for her fel-
lowship.
N-(4-Methoxybenzyl)-3-phenylprop-2-enamide (3f)
13C NMR (100 MHz, CDCl3): d = 43.3 (–), 55.3 (+), 114.1 (+),
120.5 (+), 127.7 (+), 128.8 (+), 129.3 (+), 129.6 (+), 130.1, 134.8,
141.2 (+), 159.0, 165.7.
GC-MS (EI, 70 eV): tR = 26.7 min; m/z (%) = 267 (83) [M+], 136
(100), 131 (93), 121 (43), 103 (63), 91 (10), 77 (65).
References
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( )-3-Phenyl-N-(1-phenylethyl)prop-2-enamide (3g)
13C NMR (100 MHz, CDCl3): d = 21.7 (+), 48.8 (+), 120.8 (+),
126.2 (+), 127.3 (+), 127.7 (+), 128.6 (+), 128.7 (+), 129.5 (+),
134.8, 141.0 (+), 143.1, 164.9.
COSY correlation [dH/dH]: 7.62/6.43 [3-H/2-H], 7.45/7.38–7.28 [2¢-
HPh/HPh], 7.38–7.28/7.38–7.28 [HBn/HBn], 7.38–7.28/7.45 [HPh/2¢-
HPh], 6.43/7.62 [2-H/3-H], 6.21/5.26 [H-CH/H-NH], 5.26/6.21 [H-
NH/H-CH], 5.26/1.54 [H-CH/H-Me], 1.54/5.26 [H-Me/H-CH].
(3) For structural studies, see: (a) Kruk, C.; Speargaren, K.
Spectrochim. Acta, Part A 1971, 27, 77. (b) Lewis, F. D.;
Elbert, J. E.; Upthagrove, A. L.; Hale, P. D. J. Am. Chem.
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Upthagrove, A. L.; Hale, P. D. J. Org. Chem. 1991, 56, 553.
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T. M.; Gopinath, K. W. J. Org. Chem. 1976, 41, 2571.
(b) Bernini, R.; Cachia, S.; De Salve, I.; Fabrizi, G. Synlett
2006, 2947. (c) Nair, V.; Mohanan, K.; Suja, T. D.; Biju, A.
Synthesis 2007, 1179.
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C.; Leurs, R.; Orru, R. V. A. Tetrahedron Lett. 2005, 46,
3751.
HMQC correlation [dH/dC]: 7.62/141.1 [3-H/3-C], 7.45/128.6 [2¢-
HPh/2¢-CPh], 7.38–7.28/130–125 [HAr-CAr], 7.24/129.6 [4¢-HPh/4¢-
CPh], 6.43/120.8 [2-H/2-C], 5.26/48.9 [H-CH/C-CH], 1.54/21.7 [H-
Me/C-Me].
GC-MS (EI, 70 eV): tR = 23.5 min; m/z (%) = 251 (52) [M+], 131
(100), 120 (60), 103 (62), 91 (3), 77 (54).
(R*)-3-Phenyl-N-(1-phenylethyl)prop-2-enamide (3h)
[a]D26 +83.7 (c 0.036, CHCl3).
13C NMR (100 MHz, CDCl3): d = 21.7 (+), 48.8 (+), 120.8 (+),
126.2 (+), 127.3 (+), 127.7 (+), 128.6 (+), 128.7 (+), 129.5 (+),
134.8, 141.1 (+), 143.1, 165.0.
COSY correlation [dH/dH]: 7.62/6.43 [3-H/2-H], 7.45/7.38–7.28 [2¢-
HPh/HPh], 7.38–7.28/7.38–7.28 [HBn/HBn], 7.38–7.28/7.45 [HPh/2¢-
HPh], 6.43/7.62 [2-H/3-H], 6.21/5.26 [H-NH/H-CH], 5.26/6.21 [H-
NH/H-CH], 5.26/1.54 [H-CH/H-Me], 1.54/5.26 [H-Me/H-CH].
(8) Prasad, A. K.; Husain, M.; Singh, B. K.; Gupta, R. K.;
Manchanda, V. K.; Olsen, C. E.; Parmar, S. V. Tetrahedron
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HMQC correlation [dH/dC]: 7.62/141.1 [3-H/3-C], 7.45/128.6 [2¢-
HPh/2¢-CPh], 7.38–7.28/130–125 [HAr-CAr], 7.24/129.6 [4¢-HPh/4¢-
CPh], 6.43/120.8 [2-H/2-C], 5.26/48.9 [H-CH/C-CH], 1.54/21.7 [H-
Me/C-Me].
HMBC correlation [dH/dC]: 7.62/164.9/134.8/127.7/120.8 [3-H/1-
C/2¢-CPh/1¢-CPh, 2-C], 7.45/141.1/134.8/129.5 [2¢-HPh/3-C/1¢-CPh/
3¢-CPh], 7.38–7.28/143.1/134.8/135.0–129.0/48.9 [HAr/1¢¢-CBn/1¢-
CAr/CAr-CAr/C-Me], 6.43/165.0/141.1/134.8/ [2-H/1-C/3-C/1¢-CPh],
5.25/164.9/143.1/21.7 [H-CH/1-C/1¢¢-CBn/C-Me], 1.54/143.1/48.8
[H-Me/1¢¢-CPh/C-CH].
(11) Tang, P. Org. Synth. 2005, 81, 262.
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(14) Vargas, M. L. Y.; Castelli, M. V.; Kouznetsov, V. V.;
GC-MS (EI, 70 eV): tR = 23.8 min; m/z (%) = 251 (31) [M+], 131
(100), 120 (50), 103 (52), 91 (4), 77 (49).
Urbina, G. J. M.; López, S. N.; Sortino, M.; Enriz, R. D.;
Synthesis 2008, No. 3, 377–382 © Thieme Stuttgart · New York