1438-94-4Relevant 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)
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.
Sustainable Manganese-Catalyzed Solvent-Free Synthesis of Pyrroles from 1,4-Diols and Primary Amines
Borghs, Jannik C.,Lebedev, Yury,Rueping, Magnus,El-Sepelgy, Osama
supporting information, p. 70 - 74 (2019/01/11)
A general and selective metal-catalyzed conversion of biomass-derived primary diols and amines to the highly valuable 2,5-unsubstituted pyrroles has been developed. The reaction is catalyzed by a stable nonprecious manganese complex (1 mol %) in the absence of organic solvents whereby water and molecular hydrogen are the only side products. The manganese catalyst shows unprecedented selectivity, avoiding the formation of pyrrolidines, cyclic imides, and lactones.
A new facile approach to N-alkylpyrroles from direct redox reaction of 4-hydroxy-l-proline with aldehydes
Zou, Zhiqin,Deng, Zejun,Yu, Xinhong,Zhang, Manman,Zhao, Sihan,Luo, Ting,Yin, Xin,Xu, Hui,Wang, Wei
experimental part, p. 43 - 49 (2012/03/13)
An unprecedented acetic acid-catalyzed efficient access to N-alkylpyrroles from reaction of 4-hydroxy-l-proline with a variety of aldehydes has been achieved in good to excellent yields under mild reaction conditions.
Decarboxylative formation of N-alkyl pyrroles from 4-hydroxyproline
Deb, Indubhusan,Coiro, Daniel J.,Seidel, Daniel
scheme or table, p. 6473 - 6475 (2011/06/28)
N-Alkyl pyrroles are obtained in a single step from 4-hydroxyproline and aldehydes in just 15 min under microwave irradiation.
The effect of pH on the formation of aroma compounds produced by heating a model system containing l-ascorbic acid with l-threonine/l-serine
Yu, Ai-Nong,Zhang, Ai-Dong
experimental part, p. 214 - 219 (2011/12/14)
The identification of aroma compounds, formed from the reactions of l-ascorbic acid with l-threonine/l-serine at five different pH values (5.00, 6.00, 7.00, 8.00, or 9.55) and 143 ± 2 °C for 2 h, was performed using a SPME-GC-MS technique, and further use
Iron-catalyzed inexpensive and practical synthesis of N-substituted pyrroles in water
Azizi, Najmedin,Khajeh-Amiri, Alireza,Ghafuri, Hossein,Bolourtchian, Mohammad,Saidi, Mohammad Reza
experimental part, p. 2245 - 2248 (2009/12/03)
An operationally simple, practical, and economical protocol for iron(III) chloride catalyzed Paal-Knorr pyrrole synthesis in water in good to excellent yields has been developed. Several N-substituted pyrroles are readily prepared from the reaction of 2,5-dimethoxytetrahydrofuran and aryl/alkyl, sulfonyl and acyl amines under very mild reaction conditions. Georg Thieme Verlag Stuttgart.
