Studies with azinylacetonitriles: 2-pyridylacetonitrile as a precursor to functionally substituted pyridines.
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.
Al-Sheikh
Mariam Abdullah
MA
Department of Chemistry, Girls College of Education, Jeddah, Kingdom of Saudi Arabia. r1425@hotmail.com
Elnagdi
Mohamed Hilmy
MH
D000097:Acetonitriles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry*
D000097:Acetonitriles; D011725:Pyridines; C032159:acetonitrile