
%0 Journal Article
%A Woodruff, M 
%A Polya, JB 
%T Pyrazolidine-3,5-diones with heterocyclic substituents. II. Acylation of 5-Hydrazino-3-phenyl-1H-1,2,4-triazoles
%J Australian Journal of Chemistry
%D 1975/01/01
%V 28
%N 1
%P 133-141
%K 
%R https://doi.org/10.1071/CH9750133
%U https://www.publish.csiro.au/paper/CH9750133 
%X Basic condensation of 5-hydrazino-1-methyl-3-phenyl-1H-1,2,4-triazole with diethyl malonates gives &#946;-hydrazides of malonic acids, their decarboxylated products and dihydrazides as the main products in low yields; diethyl monophenylmalonate and diethylmalonate also afford the expected pyrazolidinediones in poor yield. The corresponding &#946;-benzoyl derivative resists pyrazolidinedione formation. N1-Benzoyl derivatives of hydrazinotriazoles transacylated to the more basic hydrazine nitrogen. The 4-phenylamino derivative of 6,6-diethyl-2-phenyl-s- triazolo[1,5-a]pyrimidine-5,7(4H,6H)-dione rearranges to the corresponding pyrazolidinedione but the analogous 4- benzoyl-amino compound is demalonylated under the same conditions. Catalytic hydrogenation of the 4-(2?-propylideneimino) analogue fails and attempted reduction by sodium borohydride cleaves the pyrimidine ring. 
