1332
N. A. Randive et al.
3.81–3.85 (t, J = 6.0 Hz, 4H), 4.15–4.21 (q, J = 7.1 Hz,
4H), 5.78–5.82 (d, J = 15.1 Hz, 1H, E vinylic H),
5.84–5.87 (d, J = 10.1 Hz, 1H, Z vinylic H), 7.09–7.11
128.80, 129.06, 142.81, 143.91, 147.84, 150.72, 169.46,
170.78 ppm; MS (APCI): m/z = 220.20 (M ? 1).
Acknowledgments We acknowledge the financial support received
from the National Institute of Pharmaceutical Education and
Research.
(d, J = 10.1 Hz, 1H,
Z
vinylic H), 7.63–7.66
(d, J = 15.2 Hz, 1H, E vinylic H) ppm; 13C NMR
(100 MHz, CDCl3): d = 14.28, 34.78, 38.58, 60.26,
60.40, 60.55, 61.96, 113.71, 114.42, 146.52, 150.05,
165.47, 166.82 ppm; MS (APCI): m/z = 177.07 (M ? 1).
References
´
1. Fernandez F, Khiar N (2003) Chem Rev 103:3651
General procedure for the synthesis of ethyl
3-(substituted amino)acrylates
2. Dubbaka SR, Vogel P (2005) Angew Chem Int Ed 44:7674
3. Woodland CA, Crawley GC, Hartley RC (2004) Tetrahedron Lett
45:1227
To 0.1 g ethyl propiolate (1 mmol) in an RB flask was
added 5 cm3 demineralized water followed by amine
(1 mmol). The reaction mixture was stirred for 5 min at
room temperature. Workup of the reaction was carried out
by extracting the product with ethyl acetate, drying over
sodium sulfate, and evaporating under reduced pressure to
afford the crude product. The crude product was purified by
column chromatography on 60–120 mesh silica gel using a
mixture of EtOAc–n-hexane (12:88) as eluent. The spec-
troscopic data for the known products (3h00–3l00) were in
agreement with the reported data.
¨
4. Aucagne V, Lorin C, Tatibouet A, Rollin P (2005) Tetrahedron
Lett 46:4349
5. Harmata M, Jones DE (1996) Tetrahedron Lett 37:783
6. Detty MR, Murray BJ (1983) J Am Chem Soc 105:883
7. Wadsworth DH, Detty MR (1980) J Org Chem 45:4611
8. Hayakawa K, Kamikawaji Y, Wakita A, Kanematsu K (1984) J
Org Chem 49:1985
9. Hayakawa K, Kamikawaji Y, Kanematsu K (1982) Tetrahedron
Lett 23:2171
10. Kodomari M, Saitoh G, Yoshitomi S (1991) Bull Chem Soc Jpn
64:3485
11. Russell GA, Ngoviwatchai P (1985) Tetrahedron Lett 26:4975
12. Elassar AZA, El-Khair AA (2003) Tetrahedron 59:8463
13. Michael JP, de Koning CB, Gravestock D, Hosken GD, Howard
AS, Jungmann CM, Krause RWM, Parsons AS, Pelly SC, Stan-
bury TV (1999) Pure Appl Chem 71:979
14. Comins DL (1999) J Heterocycl Chem 36:1491
15. Malawska B (2005) Curr Top Med Chem 5:69
16. Heravi MM, Jaddi ZS, Oskooie HA, Khaleghi S, Ghassemzadeh
M (2005) J Chem Res 9:578
17. Appelbaum FC, Hunter PA (2000) Int J Antimicrob Agents 16:5
18. Baraldi PG, Simoni D, Manfredini S (1983) Synthesis 902
20. Turunen BJ, Georg GI (2006) J Am Chem Soc 128:8702
21. Epifano F, Genovese S, Curini M (2007) Tetrahedron Lett
48:2717
Ethyl (E ? Z)-3-(benzylamino)acrylate
(3m0 ? 3m00, C12H15NO2)
Yield 0.18 g (87%); slightly yellow oil; 1H NMR
(400 MHz, CDCl3): d = 1.24–1.28 (t, J = 7.1 Hz, 3H),
1.25–1.29 (t, J = 7.1 Hz, 3H), 4.09–4.15 (q, J = 7.1 Hz,
2H), 4.10–4.16 (q, J = 7.1 Hz, 2H), 4.19–4.20 (d,
J = 5.4 Hz, 2H), 4.33–4.34 (d, J = 6.0 Hz, 2H),
4.54–4.56 (d, J = 8.0 Hz, 1H, Z vinylic H), 4.78–4.81 (d,
J = 13.2 Hz, 1H, E vinylic H), 5.05 (bs, NH, E isomer),
6.66–6.71 (m, 1H, Z vinylic H), 7.25–7.37 (10H, aromatic),
7.56–7.61 (m, 1H, E vinylic H), 8.14 (bs, NH, Z isomer)
ppm; 13C NMR (100 MHz, CDCl3): d = 14.55, 14.57,
52.14, 58.72, 59.02, 82.94, 86.85, 127.35, 127.57, 127.81,
127.91, 128.49, 128.65, 137.10, 138.58, 152.07, 169.55,
170.80 ppm; MS (APCI): m/z = 206.27 (M ? 1).
22. Khosropour AR, Khodaei MM, Kookhazadeh M (2004) Tetra-
hedron Lett 45:1725
23. Englaender F, El-Chahawi M, Vogt W (1988) US Patent 4772711
24. Reddy DS, Rajale TV, Shivakumar K, Iqbal J (2005) Tetrahedron
Lett 46:979
25. Blank HU, Wolters E, Ullrich FW, Kraus H, Marzolph G, Silber
G (1991) US Patent 5030747
26. Muthusamy S, Gunanathan C, Babu SA (2002) Synthesis
471–474
Ethyl (E ? Z)-3-(1-phenylethylamino)acrylate
(3n0 ? 3n00, C13H17NO2)
27. Ke Y-Y, Li Y-J, Jia J-H, Sheng W-J, Han L, Gao J-R (2009)
Tetrahedron Lett 50:1389
Yield 0.19 g (86%); slightly yellow oil; 1H NMR
(400 MHz, CDCl3): d = 1.19–1.22 (t, J = 7.1 Hz, 3H),
1.24–1.28 (t, J = 7.1 Hz, 3H), 1.46–1.48 (d, J = 6.8 Hz,
3H), 1.51–1.53 (d, J = 6.8 Hz, 3H), 4.04–4.09 (q,
J = 7.1 Hz, 2H), 4.09–4.14 (q, J = 7.1 Hz, 2H),
4.35–4.43 (m, 2H), 4.48–4.50 (d, J = 8.1 Hz, 1H,
Z vinylic H), 4.61–4.65 (d, J = 13.3 Hz, 1H, E vinylic
H), 4.84 (bs, NH, E isomer), 6.57–6.62 (m, 1H, Z vinylic
H), 7.23–7.35 (10H, aromatic), 7.46–7.51 (m, 1H, E vinylic
H), 8.16 (bs, NH, Z isomer) ppm; 13C NMR (100 MHz,
CDCl3): d = 14.48, 14.57, 23. 28, 23.32, 57.04, 58.01,
58.70, 58.99, 82.94, 87.68, 125.69, 125.80, 128.49, 128.77,
28. Lee C-H, Lindsey JS (1994) Tetrahedron 50:11427
29. Jeon KO, Jun JH, Yu JS, Lee CK (2003) J Heterocycl Chem
40:763
30. Bhadra S, Ranu BC (2009) Can J Chem 87:1605
31. Arcadi A, Alfonsi M, Marinelli F (2009) Tetrahedron Lett
50:2060
32. Khatik GL, Kumar R, Chakraborti AK (2006) Org Lett 8:2433
33. Bates CG, Saejueng P, Doherty MQ, Venkataraman D (2004) Org
Lett 6:5005
34. Reddy VP, Swapna K, Kumar AV, Rao KR (2009) Synlett 2783
35. Liso G, Trapani G, Berardi V, Marchini P (1980) J Heterocycl
Chem 17:377
36. Cox M, Prager RH, Riessen DM (2001) Arkivoc 7:88
123