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2-[(4-Methylphenyl)[(3-methylphenyl)amino]methyl]-
cyclohexanone (12, C21H25NO)
Yield 72 %; m.p.: 124–125 °C; 1H NMR (400 MHz,
CDCl3): d = 1.60-1.82 (m, 2H), 1.82-2.10 (m, 4H), 2.25
(s, 3H), 2.35 (s, 3H), 2.35-2.55 (m, 2H), 2.70-2.80 (m, 1H),
4.65 (d, 1H, J = 7.2 Hz, anti), 6.39 (d, 1H, J = 7.6 Hz),
6.44 (s, 1H), 6.50 (d, 1H, J = 7.6 Hz), 7.00 (t, 1H,
J = 7.6 Hz), 7.16 (d, 2H, J = 7.6 Hz), 7.31 (d, 2H,
J = 8 Hz) ppm; 13C NMR (100 MHz, CDCl3):
d = 21.13, 21.48, 23.53, 27.96, 31.20, 41.70, 57.58,
57.62, 110.50, 114.57, 118.44, 127.15, 128.98, 129.21,
130.55, 136.70, 138.77, 147.33, 213.12 ppm; IR (KBr):
ꢀ
m = 3,359 (s, NH), 3,051 (w), 2,942 (m), 1,702 (s, C = O),
1,605 (s), 1,533 (m), 1,305 (m), 821 (m), 782 (m) cm-1
.
2-[[(4-Methylphenyl)amino](3-nitrophenyl)methyl]-
cyclohexanone (19, C20H22N2O3)
Yield 85 %; m.p.: 136–137 °C; 1H NMR (400 MHz,
CDCl3): d = 1.50-1.90 (m, 3H), 1.90-2.20 (m, 3H), 2.21
(s, 3H), 2.30-2.50 (m, 2H), 2.85-2.95 (m, 1H), 4.73 (d, 0.7H,
J = 5.2 Hz, anti), 4.86 (d, 0.3H, J = 4.4 Hz, syn), 6.48 (d,
2H, J = 8.4 Hz), 6.93 (d, 2H, J = 8 Hz), 7.49 (t, 1H,
J = 8 Hz), 7.80 (d, 1H, J = 7.2 Hz), 8.09 (d, 1H,
J = 8 Hz), 8.28 (s, 1H) ppm; 13C NMR (100 MHz, CDCl3):
d = 20.38, 20.40, 24.46, 24.99, 27.21, 27.85, 29.23, 31.98,
42.41, 42.53, 56.37, 57.12, 57.33, 57.91, 113.69, 114.21,
122.23, 122.36, 122.54, 127.31, 127.55, 129.32, 129.38,
129.72, 129.80, 133.72, 134.25, 144.36, 144.66, 148.41,
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35. Loh T, Chen S (2002) Org Lett 4:3647
ꢀ
210.90 (syn), 212.03 (anti) ppm; IR (KBr): m = 3,383 (s,
NH), 2,932 (m), 1,704 (C=O, syn), 1.697 (C=O, anti), 1,616
(m), 1,518 (s), 1,346 (s), 811 (s), 711 (m) cm-1
.
´
36. Ollevier T, Nadeau E, Guay-Begin A (2006) Tetrahedron Lett
47:8351
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Eur J Org Chem 5152
Acknowledgments We are grateful to Ferdowsi University of the
Mashhad Research Council for their financial support of this work
(grant: 3/16044).
38. Hong D, Yang Y, Wang Y, Liu X (2009) Synlett 1107
39. Ooi T, Kameda M, Fujii T, Maruoka K (2004) Org Lett 6:2397
40. Shen W, Wang L, Tiam H (2008) J Fluorine Chem 129:267
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