89096-77-5Relevant academic research and scientific papers
Sustainable Pathways to Pyrroles through Iron-Catalyzed N-Heterocyclization from Unsaturated Diols and Primary Amines
Yan, Tao,Barta, Katalin
, p. 2321 - 2325 (2016/10/24)
Pyrroles are prominent scaffolds in pharmaceutically active compounds and play an important role in medicinal chemistry. Therefore, the development of new, atom-economic, and sustainable catalytic strategies to obtain these moieties is highly desired. Direct catalytic pathways that utilize readily available alcohol substrates have been recently established; however, these approaches rely on the use of noble metals such as ruthenium or iridium. Here, we report on the direct synthesis of pyrroles using a catalyst based on the earth-abundant and inexpensive iron. The method uses 2-butyne-1,4-diol or 2-butene-1,4-diol that can be directly coupled with anilines, benzyl amines, and aliphatic amines to obtain a variety of N-substituted pyrroles in moderate-to-excellent isolated yields.
L-(+)-Tartaric acid and choline chloride based deep eutectic solvent: An efficient and reusable medium for synthesis of N-substituted pyrroles via Clauson-Kaas reaction
Wang, Ping,Ma, Fei-Ping,Zhang, Zhan-Hui
, p. 259 - 262 (2014/11/07)
l-(+)-Tartaric acid-choline chloride based deep eutectic solvent has been found to be an effective promoted medium for Clauson-Kaas reaction of aromatic amines and 2,5-dimethoxytetrahydrofuran. Structurally diverse N-substituted pyrroles were obtained in high to excellent yields under mild conditions. The deep eutectic solvent is inexpensive, non-toxic, reusable and biodegradable.
A recyclable magnetic nanoparticles supported antimony catalyst for the synthesis of N-substituted pyrroles in water
Ma, Fei-Ping,Li, Pei-He,Li, Bao-Le,Mo, Li-Ping,Liu, Ning,Kang, Hui-Jun,Liu, Ya-Nan,Zhang, Zhan-Hui
, p. 34 - 41 (2013/06/26)
A new magnetic nanoparticle-supported antimony catalyst was prepared and evaluated as a recoverable catalyst for Clauson-Kaas reaction. The reaction proceeds efficiently in aqueous medium to give the corresponding N-substituted pyrroles in high yield. The immobilized catalyst could be easily recovered by magnetic separation and recycled for six times without significant loss of its catalytic activity.
A convenient synthesis of pyrrolo[2,1-c][1,4] benzoxazines
Sanchez, Isabel,Pujol, Maria Dolors
, p. 5593 - 5598 (2007/10/03)
The pyrrolo[2,1-c][1,4]benzoxazine system was synthesized from 2- fluoroaniline involving an intramolecular nucleophilic displacement of the fluoride atom. The intermediate alcohols 7a and 10 were treated in basic media under strictly controlled condition
The special directing effect of fluorine: Ligand independent ortho lithiation of 1-(fluorophenyl)pyrroles
Faigl, Ferenc,Fogassy, Katalin,Szanto, Zoltan,Lopata, Antal,Toeke, Laszlo
, p. 4367 - 4374 (2007/10/03)
Lithiation of l-(fluorophenyl)pyrroles occurred exclusively ortho to the fluorine substituent independently of the structure of the tertiary amine type ligands use. Semiempirical quantum chemical calculations confirmed that the special directing effect of
Polycondensed heterocycles. VII. A convenient synthesis of pyrrolo[1,2-a]quinoxaline derivatives by intramolecular aromatic nucleophilic displacement
Campiani,Nacci,Corelli,Anzini
, p. 1567 - 1576 (2007/10/02)
4-(4-Methyl-1-piperazinyl)-7- trifluoromethylpyrrolo[1,2-a]quinoxaline (CGS 12066B) and related analogs were prepared in good overall yield through a reaction sequence involving as a key step in the intramolecular substitution of aromatic fluoride or nitr
Polycondensed Heterocycles. VI. A New Efficient Synthesis of 4H-Pyrrolobenzothiazines
Nacci, V.,Campiani, G.,Garofalo, A.
, p. 3019 - 3029 (2007/10/02)
A novel and efficient method to obtain 4H-pyrrolo benzothiazine and its 4-alkyl and 4-aryl derivatives via an intramolecular nucleophilic aromatic fluoride displacement has been developed.
