1644
A. Shaabani et al. / Tetrahedron Letters 53 (2012) 1641–1644
(300.13 MHz, DMSO-d6) d: 1.31–1.77 (10H, m, 5CH2 of cyclohexyl),
3.14 (3H, s, CH3), 3.35 (3H, s, CH3), 3.46 (1H, m, CH of cyclohexyl),
4.10 (1H, br s, NH–CH), 4.56 (1H, br s, CH–NH), 6.22–6.89 (4H, m,
CH-Ar), 8.42 (1H, br s, NH), 9.42 (1H, br s, OH). MS (EI, 70 eV), m/
z (%): 291 (M+, 5), 275 (15), 247 (100), 221 (20), 198 (70), 163
(65), 126 (90), 97 (80), 55 (90). Anal. Calcd for C16H25N3O2: C,
65.95; H, 8.65; N, 14.42. Found C, 66.12; H, 8.71; N, 14.37.
References and notes
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Ghidini, E.; Delcanale, M.; De Fanti, R.; Rizzi, A.; Mazzuferi, M.; Rodi, D.;
Simonato, M.; Lipreri, M.; Bassani, F.; Battipaglia, L.; Bergamaschi, M.; Villetti,
G. Bioorg. Med. Chem. 2006, 14, 3263–3274.
N-Cyclohexyl-2-ethoxy-2-(2-hydroxyphenylamino)acetamide
4. (a) Yang, P. S.; Rising, M. M. J. Am. Chem. Soc. 1931, 53, 3183; (b) Spoerri, K. J.
Am. Chem. Soc. 1952, 74, 1580–1582; (c) Young, B. L.; Yang, M. G.; Youn, Y. L.;
Jae, K. L. Tetrahedron Lett. 1990, 31, 1169–1170.
5. (a) Davies, S. J.; Ayscough, A. P.; Beckett, R. P.; Clements, J. M.; Doel, S.; Pratt, L.
M.; Spavold, Z. M.; Thomas, S. W.; Whittaker, M. Bioorg. Med. Chem. 2003, 13,
2715–2718; (b) Laungani, A. C.; Breit, B. Chem. Commun. 2008, 844–846; (c)
Gaeta, A.; Molina-Holgado, F.; Kong, X. L.; Salvage, S.; Fakih, S.; Francis, P. T.;
Williams, R. J.; Hider, R. C. Bioorg. Med. Chem. 2011, 19, 1285–1297; (d)
Mukaiyama, T. Tetrahedron 1981, 37, 4111–4119.
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8. (a) Ugi, I.; Cornelius, S. Chem. Ber. 1961, 94, 734–742; (b) McFarland, J. W. J. Org.
Chem. 1963, 28, 2179–2181; (c) Kreutzkamp, N.; Lammerhirt, K. Angew. Chem.,
Int. Ed. Engl. 1968, 7, 372–373; (d) Tanaka, Y.; Hasui, T.; Suginome, M. Org. Lett.
(10a)
White powder (0.23 g, 80%); mp 240–242 °C. IR (KBr) cmÀ1
:
3313, 2956, 2871, 1672, 1592, 1526, 1453. 1H NMR (300.13 MHz,
DMSO-d6) d: 1.31–1.97 (13H, m, 5CH2 of cyclohexyl and CH3),
3.15 (2H, br s, OCH2), 3.53 (1H, m, CH of cyclohexyl), 4.06 (1H, br
s, NH–CH), 4.55 (1H, br s, CH–NH), 6.25–6.89 (4H, m, CH-Ar),
8.38 (1H, br s, NH), 9.38 (1H, br s, OH). MS (EI, 70 eV), m/z (%):
292 (M+, 15), 250 (45), 211 (70), 199 (100), 184 (80), 113 (65),
104 (45), 88 (70), 57 (60). Anal. Calcd for C16H24N2O3: C, 65.73;
H, 8.27; N, 9.58. Found C, 65.57; H, 8.11; N, 9.69.
2007, 9, 4407–4410; For
a recent three-component Ugi reaction with
ammonium chloride, see: (e) Mullen, L. B.; Sutherland, J. D. Angew. Chem., Int.
Ed. 2007, 46, 8063–8066.
Acknowledgment
9. Pan, S. C.; List, B. Angew. Chem., Int. Ed. 2008, 47, 3622–3625.
We gratefully acknowledge financial support from the Research
Council of Shahid Beheshti University.
10. (a) Shaabani, A.; Soleimani, E.; Rezayan, A. H.; Sarvary, A.; Khavasi, H. R. Org.
Lett. 2008, 10, 2581–2584; (b) Shaabani, A.; Rezayan, A. H.; Keshipour, S.;
Sarvary, A.; Ng, S. W. Org. Lett. 2009, 11, 3342–3345; (c) Shaabani, A.; Sarvary,
A.; Keshipour, S.; Rezayan, A. H.; Ghadari, R. Tetrahedron 2010, 66, 1911–1914;
(d) Shaabani, A.; Sarvary, A.; Rezayan, A. H.; Keshipour, S. Tetrahedron 2009, 65,
3492–3495; (e) Shaabani, A.; Maleki, A.; Mofakham, H.; Moghimi-Rad, J. J. Org.
Chem. 2008, 73, 3925–3927; (f) Shaabani, A.; Rezayan, A. H.; Sarvary, A.;
Khavasi, H. R. Tetrahedron Lett. 2008, 49, 1469–1472.
Supplementary data
Supplementary data associated with this article can be found, in
11. Shaabani, A.; Maleki, A.; Rezayan, A. H.; Sarvary, A. Mol. Divers. 2011, 15, 41–68.