79421-35-5

Upstream product

• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 101730-62-5 1,3-bis(4-methoxyphenyl)-4-nitrobutan-1-one 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 1220957-72-1 (2Z)-4-bromo-1,3-bis(4-methoxyphenyl)-but-2-en-1-one 
• 2876-08-6 1,2-dimethyl-1H-benzimidazole 
• 219920-47-5 [3,5-Bis-(4-methoxy-phenyl)-furan-2-yl]-(4-methoxy-phenyl)-methanone 

Relevant academic research and scientific papers

β-Bromoenol phosphate as a new precursor for the modular regioselective synthesis of substituted furans

Owing to its importance in various realms of chemistry, furan occupies a position of eminence among heterocycles. Despite the availability of many methodologies for the synthesis of variably substituted furans, a modular convenient synthesis of 2,4-disubstituted furans remains challenging. The present work attempts to bridge that gap through a novel annulation-based approach using feedstock chemicals such as methyl ketones and their easily available derivatives, β-bromoenol phosphates. We have demonstrated a hitherto unknown reactivity of β-bromoenol phosphates which is responsible for the observed regioselectivity. The reaction requires only sodium hydride as the base under mild conditions. The scope of the reaction was found to be broad with the possibility of obtaining even tri-substituted furans besides a variety of 2,4-disubstituted furans. The methodology was applied to obtain synthetically challenging 3-acylfuran derivatives as well. The newly developed methodology is characterized by the modularity, regioselectivity as well as its practicality owing to easily available starting materials and fast reaction times.

Synthesis of new antineoplastic agents based on imidazo[2,1-a]pyridine

[Figure not available: see fulltext.] 2-Aryl-2-(2-aryl-2-oxoethyl)-1H,2H,3H-imidazo[1,2-a]pyridin-4-ium bromides were obtained in the reaction of (2Z)-4-bromo-1,3-diphenylbut-2-en-1-one derivatives with 2-aminopyridines in benzene. The effect of the structure of the starting reagents on the results of the reactions was studied. Antitumor activity of 2-(4-chlorophenyl)-2-[2-(4-chlorophenyl)-2-oxoethyl]-1H,2H,3H-imidazo[1,2-a]pyridin-4-ium bromide was determined, which showed high antitumor potential of the test compound on 60 human cancer cell lines.

Synthesis of azepino[1,2-a]benzimidazoles and imidazo[1,2-a]azepines

Fusion of 4-bromo-1,3-diphenyl-2-buten-1-ones (γ-bromodypnones) with 1,2-dimethyl-1H-benzimidazole and further treatment of the reaction product with a base (morpholine) gives 7,9-diaryl-5-methyl5,10-dihydroazepino[1,2-a] benzimidazol-11-ium bromides. The

Synthesis and properties of Z-1, 3-bis- (aryl)-4-bromo-2-buten-1-ones

Bromination of 1, 3-bis(aryl)-2-buten-1-ones by N-bromosuccinimide in anhydrous carbon tetrachloride gives Z-1, 3-bis(aryl)-4-bromo-2-buten-1-ones. The effect of the nature of substituent in the benzene ring on the course of a reaction with nucleophiles h

Silylation of γ-nitro ketones as a convenient approach to the synthesis of 2-[N,N-bis(silyloxy)amino]-2,3-dihydrofurans and conjugated enoximes

Silylation of γ-nitro ketones of the general formula R 1COCH(R2)CH(R3)CH(R4)NO2 proceeded stereoselectively to give 2-[N,N-bis(trimethylsilyloxy)amino]-2,3- dihydrofurans, conjugated enoximes, silylation products of the carbonyl group or both functional groups, or N,N-bis(trimethylsilyloxy)enamine depending on the nature and positions of the substituents in the carbon skeleton. Dihydrofuran derivatives are formed for R1 = Ar or cyclo-C 3H5. Enoximes are generated as the silylation products of the starting ketones with enhanced β-proton mobility (R3 = CO2Me or 4-NO2C6H4). The presence of an alkyl group at the carbonyl function (R1 = Alk) is favorable for the formation of enoximes. Finally, the introduction of a substituent at the α position with respect to the nitro group (R4 = Me, CO2Me, or Ph) leads to the formation of silyl enolates. Under the action of NH4F in MeOH, dihydrofurans can be transformed into substituted furans in moderate yields.

A convenient regioselective synthesis of 2,4-diarylfurans

A facile three step process, under mild conditions, for the synthesis of 2,4-diarylfurans with the same or different substituents on the two aryl rings, starting from benzaldehydes and acetophenones, employing Haller-Bauer type cleavage of 2-aroyl-3,5-diarylfurans is described.