31172-40-4

Upstream product

• 74-96-4 ethyl bromide 
• 98-86-2 acetophenone 
• 109-94-4 formic acid ethyl ester 
• 98-88-4 benzoyl chloride 
• 109-92-2 ethyl vinyl ether 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 64724-29-4 tributyl-((Z)-2-ethoxy-vinyl)-stannane 
• 64-67-5 diethyl sulfate 
• 41125-10-4 benzoylacetaldehyde sodium salt 

Downstream Products

• 143304-11-4 1-Ethoxycarbonyl-7-methyl-4-phenyl-quinolizinylium; bromide 
• 936352-88-4 3-benzoyl-1,4-dihydroquinolin-4-one 
• 143304-14-7 3-(6-Methyl-pyridin-2-yl)-6-phenyl-pyran-2-one; hydrobromide 
• 143304-07-8 1-Ethoxycarbonyl-4-phenyl-quinolizinylium; bromide 

Relevant academic research and scientific papers

Pharmacomodulations around the 4-oxo-1,4-dihydroquinoline-3-carboxamides, a class of potent CB2-selective cannabinoid receptor ligands: Consequences in receptor affinity and functionality

CB2 receptor selective ligands are becoming increasingly attractive drugs due to the potential role of this receptor in several physiopathological processes. Thus, the development of our previously described series of 4-oxo-1,4-dihydroquinoline-3-carboxamides was pursued with the aim to further characterize the structure-affinity and structure-functionality relationships of these derivatives. The influence of the side chain was investigated by synthesizing compounds bearing various carboxamido and keto substituents. On the other hand, the role of the quinoline central scaffold was studied by synthesizing several 6-, 7-, or 8-chloro-4-oxo-1,4-dihydroquinolines, as well as 4-oxo-1,4-dihydronaphthyridine and 4-oxo-1,4-dihydrocinnoline derivatives. The effect of these modifications on the affinity and functionality at the CB2 receptor was studied and allowed for the characterization of new selective CB2 receptor ligands.

Condensed heteroaromatic ring systems. XX. Palladium-catalyzed carbonylative coupling of iodobenzenes with (Z)-1-ethoxy-2-(tributylstannyl)ethene

Palladium-catalyzed cross-coupling reaction of iodobenzene and its 4-substituted derivatives, except for 4-nitroiodobenzene, with (Z)-1-ethoxy-2-(tributylstannyl)ethene under a carbon monoxide atmosphere (5 atm) gave the corresponding (E)-3-ethoxy-1-arylprop-2-en-1-ones in considerable yields. Syntheses of chromone and 4(1H)-quinolinone were accomplished by application of this method to 2-(methoxymethoxy)iodobenzene and ethyl 2-iodophenylcarbanylate, respectively. The results obtained on the carbonylative coupling reaction of halopyridines are also described.

1-ETHOXYCARBONYLQUINOLIZINIUM SALTS CONDENSATION OF β-KETOENOL ETHERS WITH 2-PYRIDYLACETATES

A general route to some 1-ethoxycarbonylquinolizinium bromides has been worked out.The method allow to conduct the condensation between β-ketoenol ethers and substituted 2-pyridylacetates in homogenous conditions in the presence of trifluoroacetic acid in an aprotic solvent.The substitution at C-6 in 2-pyridylacetates completely changes the reaction course affording 3,6-disubstituted 2-pyrones.

Palladium-Catalyzed Aroylation of Alkyl Vinyl Ethers. An Entry to Monoprotected 1-Aryl-1,3-dicarbonyl Equivalents

Reaction of aromatic and heteroaromatic acid chlorides with alkyl vinyl ethers in the presence of a palladium catalyst and an amine base gives the E-β-aroylated vinyl ethers 3 in moderate to good yield.The reaction proceeds under mild conditions and toler

A REGIOSPECIFIC BENZOYLATION OF ALKYL VINYL ETHERS CATALYSED BY PALLADIUM

A series of (E)-3-alkoxy-1-arylpropene-1-ones has been prepared by a regiospecific palladium-catalysed aroylation of alkylvinyl ethers.