252006-48-7

Upstream product

• 110-52-1 1,4-dibromo-butane 
• 2657-25-2 (E)-1-(4-hydroxyphenyl)-3-phenylprop-2-en-1-one 
• 100-52-7 benzaldehyde 
• 99-93-4 4-Hydroxyacetophenone 
• 97921-46-5 1,1'-((butane-1,3-diylbis(oxy))bis(4,1-phenylene))diethanone 

Downstream Products

• 1262136-54-8 C₃₄H₃₄N₄O₂ 

Relevant academic research and scientific papers

Syntheses and reactions of 4'-[(ω-bromoalkyl)oxy]-and 4',4'''-(polymethylenedoxy)-bis substituted chalcones

Base catalyzed condensation of 4-hydroxyacetophenone (1) with several aldehydes resulted 4'-hydroxychalcones (2a-c). Reaction of α,ω-dibromoalkanes (3, n=2, 4 & 6) with (2a-c) in equimolar ratio resulted a mixture of 4'-[(ω-bromoalkyl)oxy]- substituted chalcones (4a-i) and 4',4'''-(polymethylenedioxy)-bis substituted chalcones (5a-i) separated by ethanol as soluble (4a-i) and insoluble (5a-i) products. Compounds (5a-i) were also synthesized by another route. Compound 1 on treatment with 3 in molar ratio 2:1 resulted 4',4'''-(polymethylenedioxy)-diacetophenone (4#a-c) which on base catalyzed condensation gave compounds (5a-i). Reaction of 4d with substituted phenols and thiophenols gave corresponding phenoxy and thiophenoxy substituted chalcones (6a-f) where as compounds 5a, 5b, 5d, 5h and 5e on treatment with hydrazine hydrate furnished corresponding bis-2-pyrazolines (7a-e). The structures of all synthesized compounds were confirmed on the basis of analytical and spectral data.

Difunctional Heterocycles: A Convenient Synthesis of Bis(4,5-dihydropyrazolyl) ethers from Their Precursors Bis(chalcones)

The new bis(4,5-dihydropyrazolyl)ethers 18-22, 26, 27 and 40-44 were prepared in 30-80 percent yields by condensation of the corresponding bis(chalcones) 13-17 and 34-37 with each of hydrazine and phenylhydrazine. Attemptes to prepare compound 20 by alkylation of 24 with 1,4-dibromobutane were unsuccessful and instead the monoalkylated derivatives 25 was obtained in 45 percent yield. Compound 24 was obtained in 63 percent yield by reacting 23 with hydrazine hydrate in refluxing acetic acid. The bis(chalcones) 13-17 and 34-37 were obtained in 65-80 percent yields by basic condensation of each of the bis(acetyl) derivatives 8-12 and the bis(aldehyde) derivatives 30-33 with benzaldehyde and acetophenone respectively. Compounds 14, 15, 35 and 36 were alternatively obtained in 32-44 percent yields by alkylation of each of the 4-cinnamoylphenol 23 and 4-benzoylvinylphenol 38 with the appropriate dibromoalkane.