Am. Radwan et al., A NEW ROUTE FOR THE SYNTHESIS OF 1,2,4-TRIAZOLE AND 3,4-DISUBSTITUTEDCINNOLINE DERIVATIVES, Journal of the Chemical Society of Pakistan, 17(2), 1995, pp. 113-117
The behaviour of 4-aryl-hydrzono-2-phenyl-2-oxozolin-5-one towards phe
nols, aromatic amines, 1,2,4-triazol-5-amino and acylhydrazines to giv
e the 1,2,4-triazol derivatives have been studied. Fries rearrangement
products have been obtained by refluxing the products resulting from
the starting material and phenols or amines with anhydrous zinc chlori
de and acetic acid. Reactions of Fries rearrangement products with mal
ononitrile have also been studied. Interestingly, reaction of oxazolin
one derivative with or without acetophenone give one and the same prod
uct benzoylamino-6-methyl-cinnolin-4-ol. The mechanism of the later re
action has been discussed. The structure of the products has been stud
ied by different spectroscopic methods.