الفهرس 
Cyanoacetamide in heterocyclic chemistry:Only 14 pages are availabe for public view
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Abstract
Cyanoacetamide in heterocyclic chemistry: Synthesis of new
heterocycles with anticipated biological activity
This part describes the utility of 2-cyanoacetamide-N-(2-hydroxy
ethyl) (1) in the synthesis of many heterocyclic compounds such as
pyridine, imidazole, benzothiazole, chromon and thiazole derivatives.
This was achieved through the following reactions:
1. Aminopyridone derivative 2 could be obtained through condensation
of 2-cyanoacetamide-N-(2-hydroxyethyl) 1 with benzylidene
malononitrile under basic conditions.
2. Compound 2 reacted with thionyl chloride to give the corresponding
chloro derivative 3 which could be cyclized by refluxing in
dimethylformamide in the presence of anhydrous sodium carbonate to
give finally the imidazolo pyridine compound 4.
3. Compound 5 has been obtained via the reaction of ethanolamine and
benzothiazole acetyl ethyl ester which then reacted with
ethylacetoacetate, in glacial acetic acid as a solvent, in presence of
ammonium acetate to produce compound 6.
4. Coumarine derivatives 7a, b were obtained when 1 was allowed to
react with an equimolecular amount of salicylaldehyde and/or
visnaginaldehyde in boiling ethanol in the presence of triethylamine.
5. Thioglycolic acid reacted with 2-cyanoacetamide-N-(2-hydroxyethyl)
1 in dioxane to give thiazole derivative 8.
6. Similarly, compound 8 was allowed to react with salicylaldehyde to
give the Coumarine derivatives 9.
7. Other thiazole derivative 10 could be obtained upon reacting
compound 8 with equimolar amounts of benzylidene malononitrile
under basic conditions.
Summary
IV
8. The oxime and hydrazone derivatives 11a, b have been obtained via
the reaction of 1 with NaNO2 / HCl or phenyl diazonium chloride
respectively.
9. Therefore, several new products 2-11 were prepared and many of
these compounds have been biologically examined as antibacterial and
antifungal. It was found that some of them showed good results where
the more activity was associated with certain specific structural
characteristics. The assigned structures of the new products were
established by analytical and spectroscopic data, such as IR, 1H-NMR,
mass spectra and elemental analyses.
Cyanoacetyl urea in heterocyclic Synthesis: New uracils
used as antioxidants in synthetic rubber
This part describes the synthesis of some new uracil derivatives through
one step reaction as follows:
1-Cyano acetyl urea 11, as a precursor, was prepared in a good yield
from cheap and available chemicals.
2-Treatment of compound 11 with triethylorthoformate and aryl amine
derivatives in dioxane affording the uracil derivatives 13a-d.
3-Samiliraly, compound 15 and 17could also be obtained upon reacting
cyromazine 14 and / or 4-aminoantipyrene 16 respectively, with
triethylorthoformate in dioxane.
4-When, replacement of the cyano group in compound 11 by
benzothiazole has been carried out, the interesting benzothiazole uracil
derivatives 13e, f were obtained in an excellent yield.
Some of the new synthesized compounds were evaluated as antioxidants
in synthetic rubber mixes (styrene butadiene rubber) and this evaluation
confirmed by phisco-mechincal properties of vulcanizates and scanning
electron microscope.
The assigned structures of the new products were established by
analytical and spectroscopic data, such as IR, 1H-NMR, mass spectra and
elemental analyses.