M. Bararjanian et al. / Tetrahedron 67 (2011) 2644e2650
2649
(6e). Compound 6e (0.351 g, 59%) as a light-red solid; mp 100 ꢁC; Rf
(25% EtOAc/hexane) 0.45; nmax (KBr) 3410, 3286, 1694, 1632 cmꢂ1
(1H, s, NCHCO), 6.48 (1H, s, CONHC(CH3)3), 6.63e6.66 (1H, m, Ar),
6.69 (2H, d. J 8.5 Hz, Ar), 6.90e6.92 (2H, m, Ar), 6.96 (2H, d, J 8.5 Hz,
Ar), 7.30e7.53 (10H, m, Ar), 11.95 (1H, s, NHPh); dC (125 MHz,
CDCl3), 23.8 (CH3CH3CH), 28.7 (3CH3 of t-Butyl), 33.4 (CH3CH3CH),
51.8 (CHCH3CH3), 59.6 (NCHCO), 96.7, 110.3,118.7, 121.1,122.7, 123.2,
124.2, 126.7, 127.8, 127.9, 128.6, 128.7, 129.3, 130.0, 133.1, 135.4,
136.3, 136.4, 145.1, 157.5, 167.6 (C¼O), 169.1 (C¼O); HRMS (ESI):
MHþ found 544.2964. C36H38N3O2 requires 544.2965.
;
dH (500 MHz, CDCl3) 1.10e1.93 (10H, m, 5CH2 of cyclohexyl),
3.81e3.95 (1H, m, CH of cyclohexyl), 6.03 (1H, d, J 7.8 Hz, AreH4),
6.39 (1H, s, NCHCO), 6.57 (1H, d, J 7.5 Hz, CONHCH), 6.69 (1H, t, J
7.6 Hz, Ar), 6.78 (2H, d, J 8.1 Hz, Ar), 6.88(1H, d, J 7.9 Hz, Ar), 6.94
(1H, t, J 7.8 Hz, Ar), 7.01 (1H, t, J 7.4 Hz, Ar), 7.12 (2H, t, J 7.8 Hz, Ar),
7.44e7.57 (7H, m, Ar), 7.59 (2H, d, J 8.1 Hz, Ar), 11.90 (1H, s, NHPh);
dC (125 MHz, CDCl3) 24.6, 24.7, 25.4, 29.3, 29.7, 48.9 (C-cyclohexyl),
58.3 (NCHCO), 96.7, 110.1, 118.9, 121.6, 123.2, 123.6, 124.1, 124.8,
125.4, 125.5, 128.3, 128.7, 128.8, 128.9, 129.3, 129.4, 130.2, 131.8,
132.7, 135.7, 138.4, 139.1, 158.0, 166.7 (C¼O), 169.1 (C¼O); HRMS
(ESI): MHþ found 596.2525. C36H33F3N3O2 requires 596.2526.
4.3.10. 2-((Z)-3-((4-Methoxyphenylamino)(phenyl)methylene)-2-ox-
indolin-1-yl)-N-cyclohexyl-2-phenylacetamide (6j). Compound 6j
(0.474 g, 85%) as a yellow solid; mp 135 ꢁC; Rf (25% EtOAc/hexane)
0.31; nmax (KBr) 3420, 3291, 1684, 1628 cmꢂ1
; dH (500 MHz, CDCl3)
1.13e1.95 (10H, m, 5CH2 of cyclohexyl), 3.71 (3H, s, OCH3),
3.90e3.95(1H, m, CH of cyclohexyl), 5.99 (1H, d, J 7.8 Hz, AreH4),
6.33 (1H, s, NCHCO), 6.54 (1H, d, J 7.9 Hz, CONHCH), 6.63e6.67 (3H,
m, Ar), 6.75 (2H, d, J 8.9 Hz, Ar), 6.90 (2H, d, J 4.0 Hz, Ar), 7.30e7.51
(10H, m, Ar), 11.82 (1H, s, NHPh); dC (125 MHz, CDCl3) 24.7, 24.8,
25.5, 32.7, 32.8, 48.7 (C-cyclohexyl), 55.3 (OCH3), 59.1 (NCHCO),
96.1, 110.1, 114.0, 114.8, 116.4, 118.6, 121.1, 123.1, 124.3, 125.2,
127.9,128.0, 128.6, 128.8, 128.9, 129.2, 129.3, 130.0, 131.5, 133.0,
135.3, 136.1, 156.9, 158.3, 167.5 (C¼O), 169.2 (C¼O); HRMS (ESI):
MHþ found 558.2756. C36H36N3O3 requires 558.2757.
4.3.6. 2-((Z)-3-((Phenylamino)(phenyl)methylene)-2-oxindolin-1-yl)-
N-cyclohexyl-2-(4-bromophenyl) acetamide (6f). Compound 6f
(0.478 g, 79%) as a yellow solid; mp 186 ꢁC; Rf (25% EtOAc/hexane)
0.55; nmax (KBr) 3410, 3291, 1689, 1627 cmꢂ1
; dH (500 MHz, CDCl3)
1.10e1.95 (10H, m, 5CH2 of cyclohexyl), 3.82e3.97 (1H, m, CH of
cyclohexyl), 6.02 (1H, d, J 7.8 Hz, AreH4), 6.29 (1H, s, NCHCO), 6.53
(1H, d, J 7.9 Hz, CONHCH), 6.68 (1H, t, J 7.6 Hz, Ar), 6.77 (2H, d, J 7.9 Hz,
Ar), 6.87 (1H, d, J 7.9 Hz, Ar), 6.93 (1H, t, J 7.7 Hz, Ar), 7.01 (1H, t, J
7.5 Hz, Ar), 7.12 (2H, d, J 7.7 Hz, Ar), 7.28 (2H, d, J 8.5 Hz, Ar), 7.44e7.57
(7H, m, Ar), 11.91 (1H, s, NHPh); dC (125 MHz, CDCl3) 24.7, 24.8, 25.5,
32.8, 48.8 (C-cyclohexyl), 58.3 (NCHCO), 96.8,110.1,118.9,121.5,122.0,
123.2, 123.5, 124.1, 124.7, 128.7, 128.8, 128.9, 129.3, 129.4, 129.7, 130.2,
4.3.11. 2-((Z)-3-((4-Nitrophenylamino)(phenyl)methylene)-2-oxindo-
lin-1-yl)-N-cyclohexyl-2-(pyridine3-yl)acetamide(6k). Compound 6k
(0.481 g, 84%) as a light-red solid; mp 140e142 ꢁC; Rf (50% EtOAc/
131.7, 132.8, 134.2, 135.8, 138.5, 157.8, 166.9 (C¼O), 169.1 (C¼O); HRMS
79
(ESI): MHþ found 606.1762. C35
H
BrN3O2 requires 606.1764.
hexane) 0.22; nmax (KBr) 3409, 3215, 1648, 1581 cmꢂ1
; dH (500 MHz,
33
CDCl3) 1.11e1.67 (10H, m, 5CH2 of cyclohexyl), 3.85e3.95 (1H, m, CH
of cyclohexyl), 6.08 (1H, d, J 7.8 Hz, AreH4), 6.31 (1H, d, J 7.9 Hz,
CONHCH), 6.35 (1H, s, NCHCO), 6.68e6.75 (3H, m, Ar), 6.88 (1H, d, J
7.9 Hz, Ar), 6.98 (1H, t, J 7.8 Hz, Ar), 7.27e7.68 (6H, m, Ar), 7.82 (1H, d, J
7.9 Hz, Ar), 7.96(2H, d,J9.1 Hz, Ar), 8.55(1H, d, J4.3 Hz, Ar), 8.63(1H, s,
Ar),12.13(1H, s,NHPh);dC (125 MHz,CDCl3)24.7, 24.8,25.3, 32.7, 32.8,
49.1 (C-cyclohexyl), 56.4 (NCHCO), 100.4, 110.5, 119.9, 120.7, 122.2,
123.2, 123.4, 124.9, 125.1, 128.5, 130.1, 130.2, 130.8, 131.0, 132.2, 136.2,
136.4,143.1,144.9,149.1,149.3,154.8,166.0 (C¼O),169.2(C¼O); HRMS
(ESI): MHþ found 522.31207. C34H40N3O2 requires 522.31218.
4.3.7. 2-((Z)-3-((Phenylamino(phenyl)methylene)-2-oxindolin-1-yl)-
N-tert-butyl-2-phenylacetamide (6g). Compound 6g (0.416 g, 83%)
as a yellow solid; mp 190 ꢁC; Rf (25% EtOAc/hexane) 0.49; nmax (KBr)
3420, 3302, 1699, 1627 cmꢂ1
; dH (500 MHz, CDCl3) 1.39 (9H, s, 3CH3
of t-Butyl), 6.01 (1H, d, J 7.8 Hz, AreH4), 6.26 (1H, s, NCHCO), 6.42
(1H, s, CONHC(CH3)3), 6.63e6.67 (1H, m, Ar), 6.77 (2H, d, J 7.9 Hz,
Ar), 6.91 (2H, d, J 4.1 Hz, Ar), 6.99 (1H, t, J 7.5 Hz, Ar), 7.11 (2H, t, J
7.8 Hz, Ar), 7.33e7.56 (9H, m, Ar), 12.00 (1H, s, NHPh); dC (125 MHz,
CDCl3) 28.6 (3CH3 of t-Butyl), 51.8 (C-t-Butyl), 59.6 (NCHCO), 97.2,
110.3, 118.8, 121.1, 122.9, 123.1, 123.5, 124.1, 124.4, 127.9, 128.6, 128.7,
128.8, 129.3, 130.1, 132.9, 135.4, 136.5, 138.7, 157.3, 167.5 (C¼O),
169.2 (C¼O); HRMS (ESI): MHþ found 502.2499.C33H32N3O2
requires 502.2501.
4.3.12. 2-((Z)-3-((4-Fluorophenylamino)(phenyl)methylene)-2-ox-
indolin-1-yl)-N-benzyl-4-methyl pentanamide (6l). Compound 6l
(0.512 g, 96%) as a yellow solid; mp 78e80 ꢁC; Rf (25% EtOAc/hexane)
0.52; nmax (KBr) 3416, 3317, 1680, 1648 cmꢂ1
; dH (500 MHz, CDCl3)
4.3.8. 2-((Z)-3-((Phenylamino(phenyl)methylene)-2-oxindolin-1-yl)-
N-cyclohexyl-3-methylbutanamide (6h). Compound 6h (0.454 g,
92%) as a yellow solid; mp 219 ꢁC (dec); Rf (25% EtOAc/hexane) 0.45;
0.92 (3H, d, J 6.6 Hz,CH3CH3CH), 1.02 (3H, d, J 6.6 Hz, CH3CH3CH),
1.48e1.51 (1H, m, CH3CH3CH), 2.21e2.28 (2H, m, CHCH2CH), 4.46
(2H, d, J 5.8 Hz, CH2Ph), 5.30e5.50 (1H, m, NCHCO), 6.02 (1H, d, J
7.8 Hz, AreH4), 6.46e6.67 (1H, m, CONHCH2), 6.70 (1H, t, J 7.9 Hz,
Ar), 6.75e7.03 (6H, m, Ar), 7.15 (2H, d, J 7.0 Hz, Ar), 7.21e7.27 (3H, m,
Ar), 7.36 (1H, d, J 7.4 Hz, Ar), 7.43e7.55 (4H, m, Ar), 11.86 (1H, s,
NHPh); dC (125 MHz, CDCl3) 21.8 (CH3), 23.2 (CH3), 25.1 (CH3CH3CH),
36.9 (CHCH2CH), 43.4 (CH2Ph), 53.4 (NCHCO), 97.0, 110.0, 115.6 (d,
2JCeF 22.7 Hz), 118.9, 121.3, 123.7, 124.0, 125.2 (d, 3JCeF 8.2 Hz), 127.3,
127.5, 128.5, 128.7, 128.9, 129.4, 130.2, 132.5, 134.6, 135.6, 138.1, 157.7,
159.8 (d, 1JCeF 243.5 Hz),169.3 (C¼O),170.5 (C¼O); HRMS (ESI): MHþ
found 534.2559. C34H33FN3O2 requires 534.2561.
nmax (KBr) 3429, 3304, 1684, 1638 cmꢂ1
; dH (500 MHz, CDCl3) 0.79
(3H, d, J 6.6 Hz, CH3CH3CH), 1.02e1.14 (3H, m, H-cyclohexyl)), 1.17
(3H, d, J 6.6 Hz, CH3CH3CH), 1.20e1.96 (7H, m, H-cyclohexyl),
2.90e3.15 (1H, m, CHCH3CH3), 3.72e3.78 (1H, m, CH of cyclohexyl),
4.55 (1H, br s, CONHCH), 5.96 (1H, s, NCHCO), 5.99 (1H, d, J 7.8 Hz,
AreH4), 6.66 (1H, t, J 7.7 Hz, Ar), 6.77 (2H, d, J 7.9 Hz, Ar), 6.99 (2H, t,
J 7.5 Hz, Ar), 7.12 (2H, t, J 7.9 Hz, Ar), 7.27 (1H, d, J 7.5 Hz, Ar),
7.44e7.55 (5H, m, Ar),12.00 (1H, s, NHPh); dC (125 MHz, CDCl3) 19.3
(CH3CH3CH), 20.3 (CH3CH3CH), 24.6, 24.7, 25.6 (C-cyclohexyl), 27.2
(CHCH3CH3), 32.8, 48.3 (C-cyclohexyl), 74.2 (NCHCO), 97.2, 110.0,
118.7, 121.1, 122.8, 123.6, 123.8, 124.4, 128.8, 128.9, 129.4, 130.1,
132.9, 138.8, 157.3, 168.8 (C¼O), 169.6 (C¼O); HRMS (ESI): MHþ
found 494.2810.C32H36N3O2 requires 494.2810.
4.3.13. 2-((Z)-3-((Phenylamino)(phenyl)methylene)-2-oxindolin-1-
yl)-N-cyclohexyl heptanamide (6m). Compound 6m (0.474 g, 91%)
as a yellow solid; mp 117e119 ꢁC; Rf (25% EtOAc/hexane) 0.51; nmax
(KBr) 3420, 3327, 1627, 1683 cmꢂ1
; dH (500 MHz, CDCl3) 0.83 (3H, t,
4.3.9. 2-((Z)-3-((4-Isopropylphenylamino)(phenyl)methylene)-2-ox-
indolin-1-yl)-tert-butyl-2-phenyl acetamide (6i). Compound 6i
(0.484 g, 89%) as a yellow solid; mp 135 ꢁC; Rf (25% EtOAc/hexane)
J 7.0 Hz, CH3CH2), 0.86e2.41 (18H, m, CH3(CH2)4, 5CH2 of cyclo-
hexyl), 3.73e3.85 (1H, m, CH of cyclohexyl), 5.10e5.22 (1H, m,
NCHCO), 6.02 (1H, d, J 7.8 Hz, AreH4), 6.10 (1H, br, CONHCH),
6.67e6.70 (1H, m, Ar), 6.78 (2H, d, J 7.8 Hz, Ar), 6.96e7.01 (3H, m,
Ar), 7.12 (2H, t, J 7.8 Hz, Ar), 7.41e7.57 (5H, m, Ar), 11.98 (1H, s,
NHPh); dC (125 MHz, CDCl3) 13.9 (CH3CH2), 22.4 (CH3CH2), 24.7,
0.62; nmax (KBr) 3410, 3302, 1689, 1622 cmꢂ1
; dH (500 MHz, CDCl3)
1.16 (6H, d, J 6.9 Hz, CH3CH3CH), 1.40 (9H, s, 3CH3 of t-Butyl),
2.74e2.84 (1H, m, CHCH3CH3), 5.98 (1H, d, J 7.4 Hz, AreH4), 6.23