137116-92-8

Upstream product

• 23686-03-5 1,3,6-triphenyl-1,4-dihydro-pyridazine 
• 100-42-5 styrene 
• 98-86-2 acetophenone 
• 583-11-9 N-(1-phenylethylidene)phenylhydrazine 
• 59130-82-4 acetophenone phenylhydrazone 

Downstream Products

• 100-52-7 benzaldehyde 
• 137117-04-5 4-benzoyl-2-phenyl-1,2,3,4-tetrahydroquinoline 
• 768-03-6 Phenyl vinyl ketone 
• 137117-00-1 N-<4'-(3-phenyl-4,5-dihydropyrazol-1-yl)biphenyl-4-yl>acetamide 
• 137117-01-2 N-<4'-(3-phenylpyrazol-1-yl)biphenyl-4-yl>acetamide 
• 137117-06-7 phenyl(2-phenylquinolin-4-yl)methanone 

Relevant academic research and scientific papers

TEMPO-mediated Aza-diels-alder reaction: Synthesis of tetrahydropyridazines using ketohydrazones and olefins

A novel, facile, and efficient method for the synthesis of tetrahydropyridazines by a one-pot tandem reaction of easily accessible ketohydrazones and olefins in the presence of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) has been successfully developed. The reaction involves the initial generation of azoalkenes from direct oxidative dehydrogenation of ketohydrazones using TEMPO as the commercially available oxidant, followed by a subsequent aza-Diels-Alder reaction with olefins.

A new method for the generation of azoalkenes from ketohydrazones and its application to the synthesis of tetrahydropyridazine derivatives

The reaction of ketohydrazones containing an α-methylene group with chloramine-T followed by treatment with triethylamine leads to the formation of azoalkenes via an α-chloroazo-compound, which can react intermolecularly and in situ with olefinic compounds to produce tetrahydropyridazine derivatives in good yield.

Studies on the Fischer Indole Synthesis: Rearrangements of Five-, Six- and Seven-membered Cyclic Hydrazones of Pyrazoline, Tetrahydropyridazine and Tetrahydro-1,2-diazepine Series in Polyphosphoric Acid

The rearrangements of a few cyclic phenylhydrazones structurally related to 1-phenyl-Δ2-pyrazoline, 1-phenyl-1,4,5,6-tetrahydropyridazine, and 1-phenyl-4,5,6,7-tetrahydro-1,2-diazepine in hot polyphosphoric acid (PPA) are described.The five-membered-ring substrates (the pyrazolines) did not undergo the sigmatropic rearrangement typical of the Fischer indolization, the main reaction course being homolytic N-N bond cleavage, leading to benzidine and its 4-(2-benzoylethyl)-4'-(3-phenyl-Δ2-pyrazolin-1-yl) derivative.The six-membered heterocycles underwent two different reactions, both involving the tautomeric enehydrazine form: the first one is the sigmatropic rearrangement, expected for open-chain hydrazones, affording 4-acyl-1,2,3,4-tetrahydroquinoline derivatives; the second one is a retro-Diels-Alder reaction producing methyleneaniline and α,β-unsaturated carbonyl compounds.The seven-membered-ring substrate gave a 5-acyltetrahydrobenzazepine, resulting from the rearrangement, together with both a pyrrolidine and a pyrazine by-product; their formation involves homolytic N-N bond cleavage of the ring, a δ hydrogen abstraction, followed by intramolecular or intermolecular ring closure.Chemical proofs are given for the new structures.