95412-13-8

Upstream product

• 766-96-1 4-bromo-1-ethynylbenzene 
• 201230-82-2 carbon monoxide 
• 50-00-0 formaldehyd 
• 28131-17-1 2-(4-bromophenyl)acrylic acid 
• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 
• 452296-51-4 (Z)-3-(4-bromophenyl)-3-iodoprop-2-en-1-ol 
• 2028-85-5 (4-bromophenyl)diazonium chloride 
• 497-23-4 2-buten-4-olide 

Relevant academic research and scientific papers

Rhodium-Catalyzed Sequential Cycloisomerization/Aldol Addition of Cyclopropene Carboxylic Acids with Isatins

A unique, rhodium-catalyzed reaction of cyclopropene carboxylic acids with isatins has been developed, which takes place through a trapping process of transient cyclic carboxylic oxonium ylides. This reaction tolerates a wide variety of cyclopropene carboxylic acids and N-protected or unprotected isatins and represents a new, direct strategy to access valuable γ-substituted γ-butenolide architectures containing an oxindole moiety in very high yields under mild reaction conditions.

Synthesis method of butene lactone compound

The invention discloses a synthesis method of a butene lactone compound, which comprises the following steps: adding an acrylic acid compound, paraformaldehyde, pentamethyl cyclopentadienyl carbonyl cobalt diiodide, AgSbF6 and sodium acetate into an organic solvent, heating under an air condition to react, and after the reaction is completed, performing post-treatment to obtain the butene lactone compound. According to the method, the butene lactone compound is synthesized from simple and easily available raw materials through a one-pot method, the conversion efficiency is high, and the step economy is good; meanwhile, the synthesis method is simple to operate, high in reaction yield and wide in substrate universality.

Cobalt-Catalyzed Vinylic C-H Addition to Formaldehyde: Synthesis of Butenolides from Acrylic Acids and HCHO

A carboxyl-assisted C-H functionalization of acrylic acids with formaldehyde to give butenolides is described. It is the first time that the addition of an inert vinylic C-H bond to formaldehyde has been achieved via cobalt-catalyzed C-H activation. The unique reactivity of the cobalt species was observed when compared with related Rh or Ir catalysts. γ-Hydroxymethylated butenolides were produced by the treatment of Na2CO3 after the catalytic reaction in one pot.

Antifungal 3,5-disubstituted furanones: From 5-acyloxymethyl to 5-alkylidene derivatives

5-Acetoxymethyl-3-(4-bromophenyl)-2,5-dihydrofuran-2-one previously described as highly antifungally active was found to provide the corresponding 5-methylene derivative via an unusual DMSO-promoted elimination of the ester group at C5 under antifungal assay conditions. Since the latter possessed nearly the same antifungal effect as that originally reported for the former, the 5-acetoxymethyl furanone just served as a precursor of the actual antifungally active species. A few series of compounds with alkyloxy, aryloxy and alkylidene substituents at C5 of the parent furanone structure were therefore prepared and evaluated. In line with the ease of elimination of the substituent from C5, low activities of the 5-alkoxy compounds were observed. On the other hand, their 5-aryloxymethyl congeners were found to be capable of liberating the antifungally active 5-methylene furanone into the testing medium. The antifungal effect of the 5-alkylidene derivatives was highly sensitive to substitution of the alkylidene moiety; a substituent in the allylic position was necessary for a compound to retain high activity. Parallel evaluation of cytostatic activity showed moderate activities of the antifungally active derivatives against HeLa S3 and CCRF-CEM lines. Cell cycle analysis of CCRF-CEM cells following the treatment with 5-methylene-3-(4-bromophenyl)-2,5-dihydrofuran-2-one revealed that this compound is a necrotic agent.

A new regioselective synthesis of 3-substituted furan-2(5H)-ones by palladium-catalysed reductive carbonylation of alk-1-ynes

3-Alkyl- or 3-aryl-substituted furan-2(5H)-ones are obtained directly in fair yields by reductive carbonylation of alk-1-ynes in the presence of catalytic amounts of palladium iodide in conjunction with potassium iodide (10 eq.) and water (200 eq.). Simultaneous oxidation of CO to CO2 accounts for the stoichiometry of the process. Reactions are carried out in dioxane under mild conditions (80 °C and 10 atm of carbon monoxide).

INVESTIGATIONS IN THE SERIES OF SUBSTITUTED BUTAN- AND BUTENOLIDES. III. SYNTHESIS OF ARYLBUTAN- AND ARYLBUTENOLIDES AND THEIR PROPERTIES

A new method was developed for the synthesis of 2-aryl- and 3-aryl-2-buten-4-olides by the arylation of 2-buten-4-olide with diazonium halides in the presence of cupric chloride as catalyst.The intermediate products of the reaction are the corresponding arylchlorobutanolides. 4-R-Methylene-3-aryl-2-buten-4-olides and 4-hydroxy-3-aryl-2-butenamides were obtained in the reaction of 3-aryl-2-buten-4-olides with aldehydes and primary aliphatic amines respectively.Some of the synthesized compounds have antimicrobial and growth-stimulant activity.