Abstract
Nitrogen-comprising heterocyclic compounds and their derivatives have empirically been invaluable as therapeutic agents. Fundamentally, 4-chloro-6-nitro-2-amino-1,3-benzothiazole 1 was synthesized via bromination of 2-chloro-4-nitro aniline with ammonium thiocyanate. This new heterocyclic haloorganoamino-1,3-benzothiazole derivative, was a starting material, which condensed and tethered with three different aromatic aldehyde pendant arm in presence of ethanol and glacial acetic acid isolating an interesting sequence of tridentate Schiff bases 2-4. These compounds were used for complexation reactions in 1:1 (metal: ligand) stoichiometry to obtain heteroleptic Al(III), Ni (II) and K(I) benzothiazole chelates 5-7(a-c) of the type [Al(L)Cl2, Ni(L)Cl, K(L) {L = Schiff base derivatives}]. The newly synthesized complexes were characterized by the melting points, IR and some of them by 1H-NMR spectroscopy and only one by X-ray techniques. The structures of complexes were anticipated from the spectroscopic studies.
Highlights
Benzothiazole is an organic heterobicyclic compound consists of a five-membered 1,3-thiazole ring comprising nitrogen and Sulphur atoms fused to a benzene ring
4-chloro-6-nitro-2-amino-1,3-benzothiazole 1 was synthesized via bromination of 2-chloro-4-nitro aniline with ammonium thiocyanate. This new heterocyclic haloorganoamino-1,3-benzothiazole derivative, was a starting material, which condensed and tethered with three different aromatic aldehyde pendant arm in presence of ethanol and glacial acetic acid isolating an interesting sequence of tridentate Schiff bases 2-4
The key functional groups were identified via Fouriertransform infrared spectroscopy analysis, and recorded in the scanning range of 400−4000 cm-1 at room temperature on Shimadzu (FT-IR-8300S) spectrophotometer by KBr disc in Ibn Sina State Company (ISSC). 1H-NMR spectra have been used to confirm the placement of protons stating signals as δ-values in ppm for the achieved compounds, and the values are recorded on a BRUKER (400 MHz) instrument operating at 300 MHZ with tetra methyl silane as an internal standard in CDCl3 and DMSOd6 as solvent, measurements were made at the Chemistry Department, Al Baath University-Syria
Summary
Benzothiazole is an organic heterobicyclic compound consists of a five-membered 1,3-thiazole ring comprising nitrogen and Sulphur atoms fused to a benzene ring. Benzothiazole nucleus are valuable for their biological activities and found as anticancer, antimicrobial, antidiabetic, anti-inflammatory, antiviral, antileishmanial, and antiviral 4. It is known as a plant metabolite, a xenobiotic and an environmental contaminant 5. Benzothiazole derivatives linked with some heterocyclic ring such as thiadiazole have a high biological activity against some bacterial 9. Benzothiazole Schiff's base is a nitrogen analogue of an aldehyde/ketone in which the carbonyl group has been switched by an imine or azomethine group. They have been used widely as antioxidant, antimicrobial, antifungal, antiinflammatory, anticancer and cytotoxic activity 10-13
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