Beilstein J. Org. Chem.2007,3, No. 43, doi:10.1186/1860-5397-3-43
malononitrile and cyanoacetamide followed by cyclisation using anhydrous zinc chloride.
Background
The N-phenyl-3-substituted 5-pyrazolone derivatives are organic compounds that have been known since 1883; they are very useful as intermediates for pharmaceuticals and are used as anti-inflammatory agents and
Beilstein J. Org. Chem.2007,3, No. 12, doi:10.1186/1860-5397-3-12
cyclized into the corresponding oxadiazole 4 on refluxing in acetic anhydride. When refluxed in DMF in presence of piperidine, the corresponding 1,2,3-triazoleamine 5 was formed. The latter was acylated to 6 by addition of acetic anhydride while treatment of 5 with malononitrile gave the 1,2,3-triazolo
al, [14] and the possibility that the really formed product is the 5-amino-1,2,4-triazole 7. We decided to investigate further the chemical reactivity pattern of the cyclized product (Scheme 1) to support our conclusion.
Compound 5 was reacted with malononitrile in refluxing DMF to yield the