Synthesis and characterization of some new derivatives of 2-mercapto benzothiazole and evaluation their biological activity

Abstract

This work involves the synthesis of some 2-mercapto benzothiazole [1] (2-
MBT) derivatives. Compound [1] was reacted with α,β-unsaturated carbonyl
compounds (Micheal reaction) to give five new derivatives [2-6], then amide [2] reacted
with phenacyl bromide or 4-nitro phenacyl bromide in absolute ethanol to give oxazole
derivatives [7-8]. Furthermore, the reaction of amide [2] with α-chloro acetic acid or α-
bromo propionic acid in absolute ethanol afforded oxazolone derivatives [9-10].
Moreover, 2-MBT [1] reacted with ethyl α-bromo acetate in absolute ethanol giving
ester [11] which on reaction with hydrazin hydrate afforded the corresponding
hydrazide [12]. The hydrazide [12] was converted to pyrazole derivatives [13] and [14]
when reacted with acetyl acetone or ethyl aceto acetate, respectively. In addition,
treatment of hydrazide [12] with malic anhydride or phthalic anhydride in acetic acid
afforded pyridazine [15], and phthalazine derivatives [16].
The synthesized compounds were characterized by their IR, UV spectra and
C.H.N. analysis data. Some of these derivatives showed biological activities.