173260-04-3

Upstream product

• 5346-56-5 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carbonitrile 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 5417-82-3 (1-ethoxyethylidene)malononitrile 
• 100-63-0 phenylhydrazine 

Relevant academic research and scientific papers

Reaction of 5-Amino-1-phenylpyrazole-4-carbonitriles with Dimethyl Acetylenedicarboxylate. Synthesis and Structural Determination of Trimethyl 4,8-Dioxo-1-phenyl-4,5,5a,8-tetrahydro-1H-pyrazolo[3,4-e]indolizine-5,5a,6- tricarboxylate Derivatives

The reaction of 5-amino-1-phenylpyrazole-4-carbonitriles 1a-c with dimethyl acetylenedicarboxylate in the presence of potassium carbonate in dimethyl sulfoxide gave trimethyl 4,5,5a,8-tetrahydro-1-phenyl-4,8-dioxo-1H-pyrazolo[3,4-e]indolizine-5,5a,6- tric

Synthesis and chemiluminescence of 1,3-disubstituted pyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-diones and related compounds

Reactions of 1,3-disubstituted 5-aminopyrazole 5-aminopyrazole-4-carbonitrile derivatives (3a-o) with dimethyl acetylenedicarboxylate in the presence of potassium carbonate in dimethyl sulfoxide gave the corresponding dimethyl 1,3-disubstituted pyrazolo[3,4-b]pyridine-5,6-dicarboxylates (4a-o) which were allowed to react with excess hydrazine hydrate in ethanol under reflux followed by heating at 250-300°C to give 1,3-disubstituted 4-amino-1H-pyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-dione s (7a-s) in good yields. These tricyclic pyridazine derivatives were evaluated for chemiluminescence. Some were found to be more efficient than luminol in light production. 4-Amino-3-methylsulfonyl-1-phenyl-1H-pyrazolo[4',3':5,6]pyrido[2,3-d]p yridazine-5,8(6H,7H)-dione (7r) showed the greatest chemiluminescence intensity derivatives in the presence of H2O2, peroxidase, in a solution of phosphate buffer pH 8.0.