13169-72-7

Upstream product

• 109-97-7 pyrrole 
• 393-52-2 2-Fluorobenzoyl chloride 
• 79477-86-4 2-fluorophenylglyoxylic acid 
• 655-15-2 2-bromo-2'-fluoroacetophenone 
• 445-27-2 2'-Fluoroacetophenone 

Downstream Products

• 1528751-46-3 ethyl {2-[(2-fluorophenyl)carbonyl]-1H-pyrrol-1-yl}acetate 

Relevant academic research and scientific papers

Facile Synthesis of 9,10,19,20-Tetraarylporphycenes

A simple route was developed for the synthesis of 9,10,19,20-tetraarylporphycenes by combining both McMurry and oxidative synthetic strategies and using readily available precursors. The desired 5,6-diaryldipyrroethenes, which were prepared in multigram quantities over two steps, were used to prepare 9,10,19,20-tetraarylporphycenes under mild acid-catalyzed conditions. As 5,6-diaryldipyrroethene precursors can easily be prepared in multigram quantities, this method is useful for the preparation of meso-tetrarylporphycenes that contain different aryl substituents. The molecular structures of these macrocycles were determined by HRMS analysis as well as 1D and 2D NMR studies. The tetraarylporphycenes exhibited a strong Soret band at approximately 380 nm and three Q bands in the region of 580-655 nm. The tetraarylprophycenes are reasonably fluorescent and stable under redox conditions. A simple, rapid method was developed for the synthesis of meso-tetraarylporphycenes by employing a McMurry coupling followed by an oxidation reaction as the key steps. This synthetic strategy uses readily available precursors to afford 9,10,19,20-tetraarylporphycenes. The absorption, fluorescence, and electrochemical properties of these macrocycles were also studied.

Aroylation of Electron-Rich Pyrroles under Minisci Reaction Conditions

The development of Minisci acylation on electron-rich pyrroles under silver-free neutral conditions has been reported featuring the regioselective monoacylation of (NH)-free pyrroles. Unlike conventional Minisci conditions, the avoidance of any acid that could result in the polymerization of pyrroles was the key to success. The umpolung reactivity of the nucleophilic acyl radical, generated in situ from arylglyoxylic acid, could help explain the mechanism of product formation with electron-rich pyrroles. Alternatively, the nucleophilic substitution of the acyl radical on the electron-deficient pyrrole radical cation is proposed.

Design, synthesis and anxiolytic-like activity of 1-arylpyrrolo[1,2-a]pyrazine-3-carboxamides

Abstract A series of 1-arylpyrrolo[1,2-a]pyrazine-3-carboxamides were designed and synthesized as 18 kDa translocator protein (TSPO) ligands. Anxiolytic-like activity of compounds was evaluated in the open field test and elevated plus maze test. Compounds 1a and 1b demonstrated high anxiolytic-like effect in the dose range of 0.1-1.0 mg/kg comparable with that of diazepam. The involvement of TSPO receptor in the mechanism of anxiolytic-like activity of new compounds was proved by antagonism of the most active compound 1a with TSPO selective inhibitor PK11195. In vitro binding studies demonstrated high TSPO affinities for compounds 1a and 1b.

Synthesis of a new compound family, 1-aryl-3H-pyrrolo[2,1-d][1,2,5] triazepin-4(5H)-ones

Representatives of a new family, 1-aryl-3H-pyrrolo[2,1-d][1,2,5]triazepin- 4(5H)-ones have been synthesized at our laboratory as bioisosters of biologically active 1-aryl-2,3-benzodiazepine-4-ones. The efficient synthetic route described applies the synth

Silver(I)-Catalyzed conia-ene reaction: Synthesis of 3-pyrrolines via a 5-endo-dig cyclization

A novel method has been developed for the synthesis of 3-pyrrolines from β-ketopropargylamines via a 5-endo-dig carbocyclization. This transformation involves a silver-catalyzed Conia-ene type reaction tolerating broad substrate scope with good to excellent yields. Furthermore, this methodology has been extended for the construction of 2-substituted pyrroles under base-mediated conditions. Copyright

Zinc-mediated acylation and sulfonation of pyrrole and its derivatives

Pyrrole and its derivatives react smoothly with acid chlorides and sulfonyl chlorides in the presence of zinc metal in toluene at ambient temperature to afford the corresponding 2-acetyl and 2-sulfonyl pyrrole derivatives in high yields with high regioselectivity.