170939-11-4Relevant articles and documents
Pyrrolo[1,2-a]quinoxalines from chalcones: An alternate route
Togiti, Uday Kumar,Shukla, Adarash Kumar,Bhattacharya, Anupam
supporting information, (2021/04/02)
The synthesis of 2,4-disubstituted pyrrolo[1,2-a]quinoxalines from chalcones is reported. The key steps used are polyphosphoric acid (PPA) assisted acyl rearrangement of the pyrrole ring and Fe catalyzed reduction-cyclization leading to 2,4-disubstituted
Application of Polyphosphoric Acid-Mediated Acyl Migration for Regiospecific Synthesis of Diverse 2-Acylpyrroles from Chalcones
Kumar, Togiti Uday,Thigulla, Yadagiri,Rangan, Krishnan,Bhattacharya, Anupam
, p. 1283 - 1290 (2019/03/07)
A metal-free approach for the synthesis of 2-acylpyrroles is reported in this paper. Synthesis of the target molecule started from chalcones and was carried out in two steps. Initial step involved the conversion of chalcones to corresponding 4-substituted-3-acylpyrroles by reaction with TosMIC. In the subsequent step, target molecules were obtained in modest to good yields by polyphosphoric acid-mediated acyl rearrangement of 3-acylpyrroles to their 2-acyl congeners. The crucial final step was amenable to diverse substitutions on pyrrole ring. Preliminary experiment for the determination of mechanism indicated the involvement of acylium ion.
Lithium hydroxide mediated synthesis of 3,4-disubstituted pyrroles
Sharma, Ratnesh,Kumar, Kapil,Chouhan, Mangilal,Grover, Vikas,Nair, Vipin A.
, p. 14521 - 14527 (2013/09/02)
LiOH·H2O in ethanol was found to be an effective reagent for the synthesis of 3,4-disubstituted pyrrole derivatives by the van Leusen method. In situ formation of chalcones from aromatic aldehydes and enolisable ketones, and their subsequent reaction with tosylmethyl isocyanide resulted in the formation and precipitation of pyrrole derivatives from the reaction medium, in good yields. The solvation effect of the polar medium facilitates the reaction. The Royal Society of Chemistry 2013.
Antifungal agents. 9. 3-Aryl-4-[α-(1H-imidazol-1-yl)arylmethyl]pyrroles: A new class of potent anti-Candida agents
Artico,Di Santo,Costi,Massa,Retico,Artico,Apuzzo,Simonetti,Strippoli
, p. 4223 - 4233 (2007/10/03)
A new class of potent antifungal agents, namely, 3-aryl-4-[α-(1H- imidazol-1-yl)arylmethyl]-pyrroles, is described. These compounds are related to bifonazole and pyrrolnitrin, two compounds belonging to the class of antimycotic drugs. The synthesis of the title pyrroles has been performed starting from 1,3-diaryl-2-propen-1-ones, which were reacted with tosylmethyl isocyanide to give 3-aroyl-4-arylpyrroles. Reduction of the resulting compounds by lithium aluminum hydride furnished the related alcohols, which were treated with 1,1'-carbonyldiimidazole to afford the required imidazole derivatives. Forty-four new pyrroles which incorporate an (arylmethyl)imidazole moiety in the 3-arylpyrrole structure were prepared by the above procedure and tested in vitro against Candida albicans and Candida spp. Among test compounds, 10 were found to be highly active against C. albicans. The most active derivative (27) was twice as potent (MIC90) as bifonazole, and its activity was 4 times greater than those of miconazole and ketoconazole. The other nine compounds showed antifungal activity of the same order of that of bifonazole and were ca. 2 times as active as miconazole and ketoconazole. Derivatives 21 and 27 tested in vivo against C. albicans A170 were shown to be highly effective in rabbit skin candidosis. Pharmacological studies on compounds 27 and other related pyrroles (19, 35, 36, 38, 39, and 49) are in progress to select one of them as a potential candidate for clinical experiments.
