Synthesis and antimicrobial screening of 2-alkyl(aryl)-7-chloro-6-fluoro-4-(trifluoromethyl)-quinolines and their phenylacetylene derivatives, promoted by Sonogashira cross-coupling reaction

Bromo‐Substituted Diazenyl‐pyrazolo[1,5‐a]pyrimidin‐2‐amines: Sonogashira Cross‐Coupling Reaction, Photophysical Properties, Bio‐interaction and HSA Light‐Up Sensor

“…To proceed with the C−C cross‐coupling reaction, precursor 1 b was also used, which led to the formation of compounds 3 a – e . We attempted to use the same method used by our research group to obtain the compounds 2 a – e , [28] although it was impossible to obtain the respective alkynes. In some cases, the formation of compounds may not occur due to the trifluoromethylated group (CF 3 ), which is an EWG that makes the pyrazole‐pyrimidine system more deactivated.…”

“…In addition, the presence of the trifluoromethylated group (CF 3 ) in several organic compounds generates stereo‐electronic changes since this substituent has high electronegativity due to fluorine being a very electronegative atom. Given this scenario, inserting this group affects the electronic density of the heterocycles in which it is inserted, changing the electronic densities and affecting the biological and photophysical properties of the molecules [27–33] …”

Synthesis of N-Pyrrolyl(furanyl)-Substituted Piperazines, 1,4-Dizepanes, and 1,4-Diazocanes

“…The 1,3diaminopropane was chosen for this stage because of the possibility of preparing seven-membered heterocycles. The addition of the diamine was performed at 0 °C in order to favor the addition at the 4-position rather than substitution at the 5-position of enone 30 However, when using EtOH, the formation of other byproducts was observed; therefore, we decided to perform the reactions in CHCl 3 , which was more suitable for the synthesis of 4a because of the higher reflux temperature that is usually required to induce the cyclocondensation reactions. Using the solvents THF and CH 3 CN led to lower yields and the formation of a complex mixture of products, respectively.…”

“…Common solvents reported for the synthesis of trifluoromethyl enaminones are CH 2 Cl 2 and EtOH . However, when using EtOH, the formation of other byproducts was observed; therefore, we decided to perform the reactions in CHCl 3 , which was more suitable for the synthesis of 4a because of the higher reflux temperature that is usually required to induce the cyclocondensation reactions.…”

Synthesis of Alkyne-Substituted Dihydropyrrolones as Bacterial Quorum-Sensing Inhibitors of Pseudomonas aeruginosa

“…It is sometimes considered as important as the Suzuki–Miyaura reaction for the synthesis of compounds that are useful for medicinal chemistry research [ 32 ]. The Sonogashira cross-coupling reaction was featured in the synthesis of acetylenic derivatives of furanones [ 31 , 33 ] and quinolines with potential antimicrobial activity [ 34 ], as well as 2-aminoimidazole with antibiofilm activity [ 35 ]. It was also employed in the total synthesis of enediyne-containing antibiotics such as calicheamicin and dynemicin [ 36 ].…”