Journal
JOURNAL OF HETEROCYCLIC CHEMISTRY
Volume 53, Issue 3, Pages 859-864Publisher
WILEY-BLACKWELL
DOI: 10.1002/jhet.2355
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The chemical reactivity of 6-methylchromone-3-carbonitrile (1) was studied towards some nucleophilic reagents. Reaction of carbonitrile 1 with malononitrile dimer and N'-[(4-methoxyphenyl)methylidene]-2-cyanoacetohydrazide (5) gave the unexpected chromeno[4,3-b]pyridine 2 and benzoxocine-3-carbohydrazide 6, respectively. Reaction of carbonitrile 1 with 3-amino-1,2,4-triazole, 2-aminobenzimidazole, 7-chloro-4-hydrazinoquinoline and 3-hydrazino-5,6-diphenyl-1,2,4-triazine proceeds via gamma-pyrone ring opening followed by cycloaddition onto the nitrile function leading to a variety of heterocyclic systems. Structures of the new synthesized products were deduced on the basis of their analytical and spectral data.
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