KANAGARAJU & THANGAMANI, Orient. J. Chem., Vol. 30(4),1619-1630 (2014)
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64.5, 64.8, 69.3109.3, 123.2, 125.9, 126.4, 127.1,
127.6, 128.4, 128.5, 128.8, 129.1, 129.3, 129.4,
131.2, 134.2, 37.9, 139.2, 139.7, 144.6; 182.0
(oxindole carbon) 189.0 (thiophenyl carbon),Anal.
Calcd for C29H24N2O2S: C, 74.97; H, 5.21; N, 6.03; O,
6.89 ;S, 6.90. Found: C, 74.99; H, 5.20; N, 6.08 %.
5'-benzyl-3'-(thiophene-2-carbonyl)-4'-(4-
methylthiophenyl)-spiro[indoline-3,2'-pyrrolidin]-
2-one(4d)
Yield 91%, Melting point 199-202ÚC,
IR(KBr, cm-1) 1712 (thiophenyl carbonyl),
1633(oxindole carbonyl).1H NMR (CDCl3) ´: 1.65, -
NH of pyrrolidine ring (s,1H), ), 2.46 (-SCH3) (s,1H)
2.69 (H5-CH2) (dd, 1H, J = 7.6 &14 Hz), 2.98 (H5-
CH2) (dd, 1H, J = 3.2 &14 Hz), 3.83 (H4) (t,1H,J
=10.6Hz), 4.20-4.25 (H5) (m,1H) 4.37 (H3) (d, 1H,
J=10.8Hz),6.51(d,1H J=8Hz), 6.78-6.99 (m,1H),
6.86-6.90 (m,1H), 6.96 (m,1H J =8.8Hz), 6.97-7.0
(m,1H), 7.15-7.20 (m,3H), 7.22-7.28 (m,2H), 7.30-
7.33 (m,3H), 7.32-7.34 (m,2H), 7.38-7.42 (m,2H),
7.45 (d,1H, J = 8.8Hz), 7.46 (-NH of oxindole ring,),
(s,1H). 13C NMR (CDCl3) 38.7, 52.3, 64.4, 64.7, 69.1,
15.9, 109.1, 115.2, 123.2, 125.9, 126.4, 127.2,
127.6, 128.4, 129.0, 129.1, 129.4, 129.5, 131.3,
134.2, 136.1, 137.0, 137.9, 139.6, 144.9,
181.6,(Oxindole carbon) 189.0 (Thiophenyl
carbon). Anal.Calcd for C36H30N2O3S: C, 75.76; H,
5.30; N, 4.91; O, 8.41; S, 5.62. Found: C, 75.74; H,
5.26; N, 4.95 %.
5'-benzyl3'-(thiophene-2-carbonyl)-4'-(4-
methylphenyl)-spiro[indoline-3,2'-pyrrolidin]-2-
one (4b)
Yield 90%, Melting point 188-192°C,
IR(KBr, cm-1) 1712 (thiophenyl carbonyl), 1633
(oxindole carbonyl).1H NMR (CDCl3) : 1.65 (-NH
of pyrrolidine ring) (s,1H), 2.69 (H5-CH2) (dd, 1H,
J = 7.8 & 13.8 Hz) 2.99(H5-CH2) (dd, 1H, J = 2.4
&12.8 Hz), 3.85( H-4) (t,1H,J =10.8Hz), 4.40 (H-3)
(d, 1H,J =10.8Hz), 4.20- 4.25( H5) ( m,1H) 6.50
(1H,d, J = 8 Hz), 6.80 (t, 1H, J = 4 .4Hz), 6.88-6.91(m
,2H) 6.98-7.14(m ,1H), 7.16 (d ,2H J =8.4Hz), 7.19-
7.21(m ,3H), 7.24-7.27(m ,2H),7.42(d ,2H,J =8Hz),-
NH of oxindole ring, 7.78,(s,1H), 13C NMR (CDCl3)
´:15.8, 33.3, 47.2, 59.1, 59.5, 63.9, 104.0, 117.9,
120.7, 121.1, 122.3,1 23.2, 123.9, 124.2, 124.2,
124.3, 126.0, 128.9, 139.5, 176.5, (oxindole carbon
) 183.8 (thiophenyl carbon); Anal. Calcd for
C30H26N2O2S: C, 75.29; H, 5.48; N, 5.85,O,
6.69,S,6.70. Found: C, 75.33; H, 5.45; N, 5.90 %.
5'-benzyl-3'-(thiophene-2-carbonyl)4'-(4-
nitrophenyl)-spiro[indoline-3,2'-pyrrolidin]-2-one
(4e)
Yield 85%, Melting point 198-
5'-benzyl3'-(thiophene-2-carbonyl)-4'-(4-
methoxyphenyl)-spiro[indoline-3,2'-pyrrolidin]-2-
one(4c).
201°C,IR(KBr, cm-1) 1714 (thiophenyl carbonyl),
1637 (oxindole carbonyl).1H NMR (DCl3) : 1.26
(s,1H), 2.78 (H5-CH2) (dd, 1H, J = 7.4 &13.8 Hz),
2.93 (H5-CH2) (dd, 1H, J = 3.8 &13.8 Hz), 4.01 (H4)
(t,1H,J=10.4Hz), 4.33-4.34 (H5) ( m,1H) 4.38 (H3)
(d, 1H,J=10.4Hz), 6.52(1H,d, J = 7.6 Hz) , 6.82 (t,
1H, J = 4.2Hz), 6.89-6.96(m ,2H) 7.03 (t ,1H),7.13
(d,2H, J=7.2Hz) 7.17-7.24 (m,4H),7.32(d ,1H J=3.2
Hz), 7.38 (d ,1H, J =4.8), 7.67 (d, 2H J=8.4Hz),7.83-
7.90 (m,1H) 13C NMR (CDCl3) ´:39.1, 52.8, 64.7,
64.8, 69.3, 109.5, 123.3, 123.9, 124.2, 125.8, 126.6,
129.3, 132.4, 134.6, 134.7, 137.3, 139.8, 147.1,
147.4, 181.5 (oxindole carbon), 185.5, (thiophenyl
carbon). Anal. Calcd for C29H23N3O4S: C, 68.35; H,
4.55; N, 8.25; O, 12.56; S, 6.29. Found: C, 68.39; H,
4.52; N, 8.22 %.
Yield 92%, Melting point 198-
201°C,IR(KBr, cm-1) 1712 (thiophenyl carbonyl),
1639 (oxindole carbonyl).1H NMR (CDCl3) : 1.26
(-NH of pyrrolidine ring) (s,1H), 2.68 (H5-CH2) (dd,
1H, J = 7.6&14 Hz), 2.99 (H5-CH2) (dd, 1H, J = 3.2
&14 Hz), 3.78 (O-CH3) (s,3H), 3.83 (H4) (t,1H,J
=10.4Hz), 4.17-4.23 (H5) ( m,1H) 4.37 (H3) (d, 1H,J
=10.8Hz), 6.51 (1H,d, J = 8 Hz), 6.81 (t, 1H,J =
4.2Hz), 6.87-6.90 (m ,4H) 6.99-7.02 (m,1H),) 7.16-
7.20 (m,4H),7.23-7.27(m,2H) 7.33(d ,3H J =4.4Hz),
7.45(d ,3H, J =8.8), 7.78,(-NH of oxindole ring)
(s,1H),13C NMR (CDCl3),38.7, 52.0, 55.2, 64.4, 64.7,
69.2, 109.2, 114.2, 123.1, 125.9, 126.4, 127.6,
128.4, 129.1, 129.4, 129.5, 131.1, 131.2, 134.1,
138.0, 139.7, 144.7, 158.7, 181.9, (oxindole
carbon), 189.2 (thiophenyl carbon). Anal. Calcd for
C30H26N2O3S: C, 72.85; H, 5.30; N, 5.66; O, 9.70; S,
6.48. Found: C, 72.88; H, 5.28; N, 5.63 %.
5'-benzyl-3'-(thiophene-2-carbonyl)4'-(4-
fluorophenyl)-spiro[indoline-3,2'-pyrrolidin]-2-
one(4f).
Yield 94%, Melting point 198-200°C,IR
(KBr, cm-1) 1714 (thiophenyl carbonyl), 1635