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Title: Recent Developments in the Chemistry of 3-Oxoalkanenitriles
Other Titles: آخر التطورات في آيمياء 3-أوآسو ألكان النيتريل
Authors: Aisha Yousif Adam Mohammed 
Supervisor: Dr. Hamad M. Al-Mater
Keywords: 3-Oxoalkanenitriles
Issue Date: 2011
Publisher:  Kuwait university - college of graduate studies
Abstract: The reaction of N-methylpyrrole with cyanoacetic acid and acetic anhydride mixture afforded 2-cyanoacetyl-1-methylpyrrole. The synthesized 2-cyanoacetyl-1-methylpyrrole was found to react with acetylacetone and ethyl acetoacetate in glacial acetic acid in presence of ammonium acetate to yield a polysubstituted pyridine derivative and a pyran derivative respectively. The pyran derivative was formed via unprecedented rearrangement process. The enaminonitrile, generated by reaction of 2-cyanoacetyl-1-methylpyrrole with the dimethylformamide dimethylacetal (DMFDMA), undergoes condensation with malononitrile to yield a pyrrole-substituted pyridine again via novel rearrangement pathway. Structural assignments of 2-cyanoacetyl-1-methylpyrrole, enaminonitrile, pyrrole-substituted pyran, and pyridine were made by X-ray crystallographic analysis. 2-Cyanoacetyl-1-methylpyrrole undergoes coupling with benzenediazonium chloride to yield the arylhydrazone that reacts with hydroxylamine hydrochloride to yield an amidoxime that readily cyclize to pyrrole-substituted 1,2,3-triazole whose structure could be also established by X-ray.
Appears in Programs:0420 Chemistry (M.Sc.)

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