74204-92-5

Upstream product

• 5891-21-4 5-chloro-2-pentanone 
• 100-63-0 phenylhydrazine 
• 768-60-5 4-methoxyphenylacetylen 
• 765-43-5 Cyclopropyl methyl ketone 
• 59-88-1 phenylhydrazine hydrochloride 
• 39998-48-6 1-phenyl-3-methylhexahydropyridazine 

Downstream Products

• 6220-79-7 4-phenylamino-butan-2-one 
• 137117-02-3 4-acetyl-1,2,3,4-tetrahydroquinoline 
• 137117-03-4 4-(4-acetyl-1,2,3,4-tetrahydroquinolin-1-yl)butan-2-one 

Relevant academic research and scientific papers

Synthesis of 1-Aza-6,7-dehydrotropanes via Copper(I)-Catalyzed Coupling of 5-Chloropentan-2-one with Hydrazines and Terminal Alkynes

A one-pot, three-component, Cu(I)-catalyzed coupling of primary hydrazines, 5-chloropentan-2-one, and terminal alkynes was developed. The resulting 1-aza-6,7-dehydrotropanes compose a new class of substances while related 1-azatropanes are scarcely described in literature and closely resemble tropane alkaloids. Hydrogenation of the double bond in 1-aza-6,7-dehydrotropanes triggered a rearrangement, involving a [1,3]-hydride shift, forming cyclic hydrazones.

Synthesis and cytotoxic properties of tryptamine derivatives

Abstract The cyclopropyliminium and subsequent Grandberg rearrangements of cyclopropylketone hydrozones lead to the formation of tryptamines, which were additionally substituted at either the aromatic ring atoms or the amino group. The products were tested for their cytotoxic properties against HepG2, Jurkat and HEK293 cell lines using MTT assay. The highest activity as well as the highest selectivity was found amongst the compounds derived with one benzyl substituent at the amino group. The flow cytometry technique revealed cell-type specificity in terms of the mechanism of viability inhibition. Thus, the compounds were found to induce mainly apoptosis in HEK293 and HepG2 cells, while Jurkat cells displayed late apoptotic and necrotic responses. The apoptosis pathway is most likely to include mitochondrial damage.

The rearrangement of cyclopropylketone arylhydrazones. Synthesis of tryptamines and tetrahydropyridazines

The cyclopropyliminium rearrangement of cyclopropylketone arylhydrazones may result in two possible products. The first one forms via cyclopropane ring-opening and ring-closure to give six-membered tetrahydropyridazines. The second is formed via ring-closure resulting in a five-membered ring and subsequent Grandberg rearrangement into a tryptamine. The product ratio depends on the nature of the starting hydrazones.

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.

CYCLIZATION OF 1-THIOCARBAMOYL-2-PHENYLPYRAZOLIDINES

Thiocarbamoyl derivatives of N-phenylpyrazolines are converted under the influence of acidic agents to mixture of tetrahydropyrimidobenzothiazoles and 2-imino-3-aminoalkylbenzothiazoles and not only to tetrahydropyrimidobenzothiazoles, as previousl