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Part – B Studies on isatin derivatives…..
The same group 240 also prepared aminoacetylindolediones (1) (R = 5-
F, 6-F; NR 1 R 2 = NMe2, NEt2, morpholino, piperidino) by cyclizing
fluoroisonitrosoacetanilides with acid, chloroacetylating the
fluoroindolediones, and aminating the chloroacetyl derivatives. (2) [R 3 = 4-F,
4-Cl, 4-NO2, 2, 4-(NO2)2] were obtained by Mannich reaction of the
fluoroindolediones with morpholine and reaction with phenyl hydrazines.
(R 3 C6H4NHNH2) (Fig. B.1.11)
R
R
R
N
H
N N
O
O
N
CH 2
N
O
HN
O
N
COCH 2 NR 1R 2
2
S
I
N
N
O
N
1
CHR 2
R
SCH 2CH 2 N(R 1 )2
They 241 further reported that Mannich reaction of indolediones (1) (R =
H; R 1 = 4-CF3, 5-F, 6-F; X = O) and amines (R 2 H = morpholine, piperidine)
gave 46-73 % (1) (R = CH2R 2 ). Treating (1) (R = H; R 1 = 4-CF3, 5-F, 6-F; X =
O) with R 3 NH2 (R 3 = 4-FC6H4, 3-CF3C6H4) gave 71-82 % (1) (X = NR 3 ), which
underwent Mannich reaction with R 2 H to give 50-64 % (1) (R = CH2R 2 ).
Refluxing thiosemicarbazide with (1) (R =H, X = O) in K2CO3-H2O gave 78-82
% 1, 2, 3-triazino [5, 6-b] indole-3-thiones (2). Successive treatment of (2) with
Department of Chemistry, Saurashtra University, Rajkot-360 005 122
II
R
NNH
O
I
N
CH 2 N O
1 2
Fig. B.1.11
Fig. B.1.10
O
N O
H III
R 3
3
II