Page 210 - 80_01
P. 210
Krishna
Naik&
col.
NaNO2 + HCl R NH2
0 - 5 oC
R N=N Cl
(I)
+
CH3COCH2COOC2H5
CH3COONa
+R H2N NH OH
NH N=C COCH3
COOC2H5
Microwave
irradiation DMF
(II) 150W
ClCH2COOC2H5 + R NH N CH3
O N
K2O3 (anhydrous) N
DMF
(III)
OH
R NH N CH3 N2H4, H2O R NH N CH3
O N Ethanol O N
N N
(IV) (V)
H
O CO
O O C N NH2
R=H, CH3, OCH3, OC2H5, Cl, Br. O
Scheme
1.--Synthesis
of
{4--[3--Methyl--5--oxo--4--(4|--substituted
phenyl
hydrazono)--4,5--dihydro--
pyrazol--1--yl]--phenoxy}--acetic
acid
hydrazide
(V).
R NH N CH3 R NH N CH3
O N O N
N Acetophenone / N
glacial AcOH
(V) (VI) NH N=C
O C NH NH2
O O C R1
O
R2
R NH N CH3 R NH N CH3
N N
Acetic anhdride
ON ON
(VI) NH N=C (VII) R1
O C R1 O O R2 O
O R2 N C CH3
N
R = -H, -CH3, -OCH3, -OC2H5, -Cl, -Br, R1 = -CH3, R2 = -C6H5, p-
CH3C6H4,p-ClC6H4, p-OCH3C6H4,p-NO2C6H4.
Scheme
2.--
Synthesis
of
2--(4--acetyl--5--methyl--5--phenyl--4,5--dihydro--[1,3,4]oxadiazole--2--
yl(methyl)--5--methyl--4(4|--phenyl
hydrazono)--2,4--dihydrazono--pyrazol--3--one
(VII).
2
04
