137596-50-0Relevant academic research and scientific papers
Synthesis of some diguanidino 1-methyl-2,5-diaryl-1H-pyrroles as antifungal agents
Jana, Gour Hari,Jain, Sanjay,Arora, Sudershan K.,Sinha, Neelima
, p. 3592 - 3595 (2005)
A series of novel 2,5-bis(guanidino-aryl)-1-methyl-1H-pyrroles 9a-h has been synthesized starting from 1-methyl-1H-pyrrole. The antifungal activities of compounds were evaluated by in vitro agar diffusion and broth dilution assay against Candida spp. and Aspergillus spp. Compound 9c from this series was found to be equipotent or more potent than fluconazole, whereas compound 9d was comparable to fluconazole against most of the tested strains.
Synthesis of 2,5-diarylpyrroles by ligand-free palladium-catalyzed ch activation of pyrroles in ionic liquids
Ehlers, Peter,Petrosyan, Andranik,Baumgard, Jens,Jopp, Stefan,Steinfeld, Norbert,Ghochikyan, Tariel V.,Saghyan, Ashot S.,Fischer, Christine,Langer, Peter
, p. 2504 - 2511 (2013/08/23)
The palladium-catalyzed CH activation and arylation of N-methylpyrrole and N-phenylpyrrole allowed a convenient synthesis of diarylpyrroles. The reactions were performed by using tetrabutylammonium acetate as an ionic solvent, which allowed for the application of a ligand-free catalytic system by using simple palladium salts or polyvinylpyrrolidone-stabilized palladium nanoparticles as the catalyst.
Palladium-Catalysed Direct Polyarylation of Pyrrole Derivatives
Zhao, Liqin,Bruneau, Christian,Doucet, Henri
, p. 255 - 262 (2013/03/28)
The palladium-catalysed direct polyarylation of 1-methylpyrrole and 1-phenylpyrrole was studied. As the C2 and C5 positions of pyrroles are more reactive for C-H bond functionalisation than the C3 and C4 positions, the formation of 2,5-diarylpyrroles was
Synthesis of dicationic 2,5-diarylpyrroles
Arafa, Reem K.,Brun, Reto,Werbovetz, Karl A.,Tanious, Farial A.,David Wilson,Boykin, David W.
, p. 423 - 428 (2007/10/03)
A new series of dicationic reversed amidine derivatives 4a-f and a substituted guanidine analog 7 of 2,5-diarylpyrrole obtained starting from the corresponding 2,5-bis(aminoaryl)pyrroles 3a-c are reported. The results of DNA binding studies and antimicrob
Intermediates in the Paal-Knorr Synthesis of Pyrroles
Amarnath, Venkataraman,Anthony, Douglas C.,Amarnath, Kalyani,Valentine, William M.,Wetterau, Lawrence A.,Graham, Doyle G.
, p. 6924 - 6931 (2007/10/02)
The mechanism of Paal-Knorr reaction between a 1,4-dicarbonyl compound and ammonia or a primary amine to form a pyrrole is explored.In aprotic solvents and in aqueous solutions near neutrality, d,l diastereomers of 3,4-dimethyl- and 3,4-diethyl-2,5-hexanediones (1r and 2r) formed pyrroles 1.3-57.0 times faster than the corresponding meso diastereomers (1m and 2m).This contradicts any intermediate, such as the enamine 15, which does not remain saturated at both the 3- and 4-positions through the rate-determining step.The demonstrated stereoisomeric difference in reactivity coupled with the following results support the hemiaminal (9) as the intermediate undergoing cyclization in the rate-limiting step of the Paal-Knorr reaction: (1) The reaction rate was adversely affected by increase in the size of the alkyl substituents on the dione. (2) Racemic 2,3-dimethyl-1,4-diphenyl-1,4-butanedione (3r) was more reactive toward ammonium acetate (2.2:1) and 2-aminoethanol (11.2:1) than the meso isomer (3m), ruling out the involvement of the less substituted enamine 14. (3) The relative rate of pyrrole formation of 1,4-diphenyl-1,4-butanedione (5) and its dimethoxy (6) and dinitro (7) derivatives (1:0.3:6) does not support cyclization of the imine (11) to the pyrrolinium ion (12). (4) The rates of reaction of 2,2,3,3-tetradeuterio-1,4-diphenyl-1,4-butanedione (5D) and perdeuterio-2,5-hexanedione (4D) were very close to those of unlabeled diketones, indicating the absence of a primary isotope effect in the reaction. (5) Neither the isomerization of the unreacted diastereomers of 1, 2, and 3 nor hydrogen exchange of 4D and 5D was detected during the reaction.
