1,2,4-triazole carboxylic-acid or ester
Additional step: nucleophile substitution with hydrazine.
SMARTS: [CH0;$(C-[#6]):1]#[NH0:2].[CH0;$(C-[#6]);R0:5](=[OD1])-[#8;H1,$(O-[CH3]),$(O-[CH2]-[CH3])]>>[N:2]1-[C:1]=N-N-[C:5]=1
Conditions
Reactant 1: nitrile.
Reactant 2: carboxylic acid or ester.
R1, R2: aryl, alkyl. R3: H, methyl, ethyl.
References
G. M. Castanedo, P. S. Seng, N. Blaquiere, S. Trapp, S. T. Staben, J. Org. Chem., 2011, 76, 1177-1179.
Other sources
Organic chemistry