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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

1,*  and 2
1 Department of Chemistry, Girls College of Education, Jeddah, P. O. Box 138016, Jeddah 21323, Kingdom of Saudi Arabia 2 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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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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