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Molecules 2009, 14(11), 4406-4413; doi:10.3390/molecules14114406

Studies with Azinylacetonitriles: 2-Pyridylacetonitrile as a Precursor to Functionally Substituted Pyridines

Department of Chemistry, Girls College of Education, Jeddah, P. O. Box 138016, Jeddah 21323, Kingdom of Saudi Arabia
Department of Chemistry, Faculty of Science, Kuwait University, Kuwait
Author to whom correspondence should be addressed.
Received: 7 September 2009 / Revised: 27 October 2009 / Accepted: 28 October 2009 / Published: 3 November 2009
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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.
Keywords: 2-pyridylacetonitrile; enaminonitrile; arylhydrazones 2-pyridylacetonitrile; enaminonitrile; arylhydrazones
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Al-Sheikh, M.A.; Elnagdi, M.H. Studies with Azinylacetonitriles: 2-Pyridylacetonitrile as a Precursor to Functionally Substituted Pyridines. Molecules 2009, 14, 4406-4413.

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