Turkish Journal of Chemistry, Vol.28, No.3, 311-323, 2004
A convenient synthesis of 3,6-disubstituted-1,4-dihydro-[1,2,4,5] tetrazines and preparation of new acetic acid derivatives containing 5-oxo-4-phenylamino-4,5-dihydro-[1,2,4]triazole
series of compounds 8a-e, was synthesized by condensation of compounds 7a-e with ethyl bromoacetate. The treatment of compounds 8a-e with hydrazine hydrate afforded the corresponding hydrazide derivatives (9a-e). Subsequently, compounds 9a-e were converted to alkylidene hydrazides (10a-e). Moreover, upon heating in the presence of carboxylic acids, compounds 9a-e unexpectedly gave 1,4dihydro-(1,2,4,5)tetrazine derivatives (11a-e).
Keywords:conformer;geometrical isomer;ethyl bromoacetate;imine bond;5-oxo-[1,2,4]triazole;[1,2,4,5)tetrazine