Synthesis of Some New Antipyrine Derivatives

الملخص

In this work, 4-chloro acet amide derivative [2] was prepared from 4-amino
antipyrine [1] and chloro acetyl chloride then converted into thiozolidine-4-one [3] on
reaction with KSCN. Subsequent refluxing of compound [3] with 3-nitrobenzaldehyde
in the presence of NaOAC-acetic acid gave the derivative [4]. The hydrazide derivative
[5] was prepared from the 4-chloro acet amide derivative [2] and hydrazine hydrate,
which upon refluxing with acetyl aceton in absolute ethanol yielded antipyrine
containing pyrazol moiety [6], refluxing of compound [2] with some amines in absolute
ethanol afford the corresponding acetamide derivatives [7-10]. Moreover, reaction of [1]
with CS2 and KOH afforded the salt [11], which upon reaction with hydrazine hydrate at
45-55oC for 1hr, yielded the fused ring derivative [12].
The Schiff base [13] was prepared from 3-nitro benzaldehyde and compound [1], and
then oxidized by KMno4 into the acid derivative [14]. Diazotization of compound [1]
with NaNo2/HCl led to azo derivative [15] which is reacted with acetyl acetone to give
compound [16]. Reaction of compound [[16] with hydrazine led to ring closure giving
derivative with pyrazole moiety [17]. Furthermore, reaction of [1] with tetrahydrofuran
in acetic acid gave derivative with pyrrolidin moiety [18].