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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Studies with azinylacetonitriles: 2-pyridylacetonitrile as a precursor to functionally substituted pyridines
Mariam Abdullah Al-Sheikh1, Mohamed Hilmy Elnagdi
1Department of Chemistry, Girls College of Education, Jeddah, Kingdom of Saudi Arabia. r1425@hotmail.com
Abstract:
2-Pyridylacetonitrile (1) couples with aromatic diazonium salts to yield arylhydrazones 2a-c, that were shown to exist in the syn-form 2 rather than the anti-form 4. Compounds 2a,c reacted with hydroxylamine in refluxing DMF to yield the interesting 1,2,3-triazolylpyridines 6. Attempts to cyclize 2 to give the corresponding fused pyrazolopyridines 9 failed. On the other hand, compound 1 condensed with dimethylformamide dimethyl acetal to yield enaminonitrile 10 that could be converted into pyrazolylpyridine 11.
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