73654-16-7

Upstream product

• 73654-17-8 4-((Z)-3-Oxo-3-phenyl-propenyl)-benzaldehyde 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 1122-91-4 4-bromo-benzaldehyde 
• 100-52-7 benzaldehyde 
• 623-27-8 terephthalaldehyde, 
• 98-86-2 acetophenone 
• 583-06-2 3-benzoylacrylic acid 
• 66885-68-5 (E)-p-formylcinnamic acid 
• 611-73-4 Benzoylformic acid 

Downstream Products

• 73654-17-8 4-((Z)-3-Oxo-3-phenyl-propenyl)-benzaldehyde 
• 1414806-50-0 (S)-2-((Z)-4-oxo-5-(4-((E)-3-oxo-3-phenylprop-1-en-1-yl)benzylidene)-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid 

Relevant academic research and scientific papers

Iron-facilitated oxidative radical decarboxylative cross-coupling between α-oxocarboxylic acids and acrylic acids: An approach to α,β-unsaturated carbonyls

The first Fe-facilitated decarboxylative cross-coupling reaction between α-oxocarboxylic acids and acrylic acids in aqueous solution has been developed. This transformation is characterized by its wide substrate scope and good functional group compatibility utilizing inexpensive and easily accessible reagents, thus providing an efficient and expeditious approach to an important class of α,β-unsaturated carbonyls frequently found in bioactive compounds. The synthetic potential of the coupled products is also demonstrated in subsequent functionalization reactions. Preliminary mechanism studies suggest that a free radical pathway is involved in this process: the generation of an acyl radical from α-oxocarboxylic acid via the excision of carbon dioxide followed by the addition of an acyl radical to the α-position of the double bond in acrylic acid then delivers the α,β-unsaturated carbonyl adduct through the extrusion of another carbon dioxide.

Synthesis and evaluation of the antibacterial activities of aryl substituted dihydrotriazine derivatives

Five series of dihydrotriazine derivatives containing chalcone (13a–i), phenoxy acetophenone (14a–b), benzyl benzene (15a–c), naphthoxyl acetophenone (16a–b) and benzyl naphthalene (17a–h) moieties were designed and synthesized. The antibacterial and antifungal activities of these compounds were evaluated against several strains of Gram-positive and Gram-negative bacteria, as well as a single fungus. Compound 17h was found to be the most potent of all of the compounds tested, with an MIC value of 0.5 μg/mL against several Gram-positive (Staphylococcus aureus 4220 and QRSA CCARM 3505) and Gram-negative (Escherichia coli 1924) strains of bacteria. However, this compound was inactive against Pseudomonas aeruginosa 2742 and Salmonella typhimurium 2421, indicating that its antibacterial spectrum is similar to those of the positive controls gatifloxacin and moxifloxacin. The cytotoxic activity of the compound 13i, 16b and 17h was assessed in Human normal liver cells.

Palladium-catalyzed decarboxylative arylation of benzoylacrylic acids toward the synthesis of chalcones

It has been found that readily available 3-benzoylacrylic acids undergo palladium-catalyzed decarboxylative arylation with arylboronic acids in the presence of a copper salt oxidant to produce chalcone derivatives. The decarboxylative arylation could also be achieved using aryl halides as the alternative aryl source to expand the applicable scope.

Synthesis and antimicrobial evaluation of L-phenylalanine-derived C5-substituted rhodanine and chalcone derivatives containing thiobarbituric acid or 2-thioxo-4-thiazolidinone

Four novel series of compounds, including the l-phenylalanine-derived C5-substituted rhodanine (6a-q, 7a-j) and chalcone derivatives containing thiobarbituric acid or 2-thioxo-4-thiazolidinone (9a-e, 11a-e) have been designed, synthesized, characterized, and evaluated for their antibacterial activity. Some of these compounds showed significant antibacterial activity against Gram-positive bacterias, especially against the strains of multidrug-resistant clinical isolates, among which compounds 6c-e, 6g, 6i, 6j and 6q exhibiting high levels of antimicrobial activity against Staphylococcus aureus RN4220 with minimum inhibitory concentration (MIC) values of 2 μg/mL. Compound 6q showed the most potent activity of all of the compounds against all of the test multidrug-resistant clinical isolates tested. Unfortunately, however, none of the compounds were active against Gram-negative bacteria at 64 μg/mL.

Synthesis of new chalcone derivatives containing a rhodanine-3-acetic acid moiety with potential anti-bacterial activity

With an intention to synergize the anti-bacterial activity of chalcones and rhodanine-3-acetic acid, several hybrid compounds possessing chalcone and rhodanine-3-acetic acid moieties were synthesized and tested for their anti-bacterial activity. Some comp

Coupling-isomerization synthesis of chalcones

The Sonogashira coupling of electron-deficient (hetero)aryl halides 1 and (hetero)aryl or alkenyl 1-propargyl alcohols 2 does not terminate at the stage of the expected internal propargyl alcohols, but rather gives rise to the formation of α,β-unsaturated ketones 3 with a variety of acceptor substituents. This new domino reaction, a coupling-isomerization reaction (CIR), can be rationalized as a sequence of rapid Pd/Cu-catalyzed alkynylation followed by a slow amine-base-catalyzed propargyl alcohol-enone isomerization. Performing the CIR in deuterated protic solvents or with a selectively deuterated propargyl alcohol revealed that the base-catalyzed isomerization step proceeds through a formal 1,3-H shift with minimal H/D exchange with the surrounding solvent. Additionally, 19F NMR kinetic measurements on the isomerization step with the fluorinated propargyl alcohol 4r support the mechanistic rationale.

An unexpected coupling-isomerization sequence as an entry to novel three-component-pyrazoline syntheses

A novel retrosynthetic approach to 3,5-diaryl-2-pyrazolines is provided by a three-component, one-pot reaction initiated by a palladium/copper- catalyzed cross-coupling (see scheme). The initially formed enone cyclocondenses in situ with the hydrazine to