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Part – B Studies on isatin derivatives…..
of 3-aminopropanol (1) with formaldehyde and 1, 1-dinitroethane or 2-bromo-
2, 2-dinitroethanol gave the 1, 3-oxazines (2) (R = Me, Br). Similar reaction of
(1) with oxalamide and succinamide gave the bis (oxazinyl) diamides (3) (X =
bond, CH2CH2) and reaction of 2-aminoethanol with formaldehyde and
benzotriazole gave the oxazolylmethylbenzotriazole. (Fig. B.1.19)
R
O2N
NO 2
1
N O
II
O O
O N N X N N O
H H
3
N
N
N
Furthermore they 250 reported that the reactions of RH (RH = isatin,
benzotriazole, and succinimide) with formaldehyde and methylamine yield
monoamines (RCH2N(Me)CH2R) and methylenediamines.
(RCH2N(Me)CH2N(Me)CH2R) The use of ethylenediamine as the amino
component affords N, N'-disubstituted imidazolidines, while the reactions with
3-aminopropanol give N-substituted tetrahydro-1, 3-oxazines. RCH2NBui2
was obtained from succinimide, formaldehyde, and diisobutylamine.
Nitrosative cleavage of the amines obtained was studied: monoamines and
methylenediamines give N-nitrosoamines. (RCH2N(NO)Me) RCH2NBui2
affords diisobutylnitrosamine, while imidazolidines transform into dinitroso
compounds. (RCH2N(NO)CH2CH2N(NO)CH2R) (Fig. B.1.20)
Department of Chemistry, Saurashtra University, Rajkot-360 005 126
N
O
2
Fig. B.1.20
IV
III
Fig. B.1.19