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New Journal of Chemistry
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Journal Name
ARTICLE
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Sun, B.-X. Du, H.-H. Zhang, L. Ji, F. Shi, CDhOemI: 1C0a.1t0C3h9e/Cm9,N2J0013250,97F,
1211.
pTsOH to the same reaction is facilitating the elimination of the
water molecule and addition of second nucleophile (Friedel-
Crafts alkylation). The proposed transition states are shown
below (Figure-6).
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47, 5819.
NH
NH
N
HN
O
CH3
O
HN
O
O
O
-
H
O
H
A
A
r
r
H
O
H
-
OH
H
O
H
-
HO
S
S
O
-
-
O
N
R1
H
N
H
-
H
H
O
H
O
O
O
O
H
O
H
H
O
H
R
O
O
-H2O
-H2O
H
O
H
O
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
H
H
HN
O
H
H
H
O
O
H
H
H
H
H
H
H
H
O
N
O
O
H
H
H
H
O
H
O
H
H
H
H
O
H
H
H
H
H
O
O
O
O
O
H
H
H
H
(III)
R = OH, N(CH3
H
H
H
O
O
H
(II)
)
2
(I)
Figure-6: Proposed reaction transition states for retro-Henry reaction followed by
Friedel-Crafts alkylation reactions.
In conclusion, we have developed a new protocol for the
selective synthesis of 3-hydroxy-3-(1H-indol-3-yl)indolin-2-ones
and bis-indolyl-2-oxindoles (symmetrical and unsymmetrical)
via retro-Henry followed by Friedel-Crafts alkylation reactions.
Further, the developed method was extended for 2-(3-hydroxy-
2-oxoindolin-3-yl)acetic acid derivatives which can be
converted in to natural products. This is the first example for
the exploitation of nitro functionality present in 3,5-dimethyl-4-
nitroisoxazole for the retro-Henry type reaction.
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Acknowledgments
SN thanks UGC-New Delhi for the fellowship. KS thanks DST for
the INSPIRE fellowship. BP thanks MHRD-NITW for fellowship.
DK thanks DST (SERB), New Delhi for the financial support
(SB/FT/CS-136/2012and SB/EMEQ-103/2014).
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