5044-40-6

Upstream product

• 52768-17-9 4-(1H-pyrrol-1-yl)aniline 
• 50-00-0 formaldehyd 
• 6117-80-2 1,4-butenediol 
• 99-98-9 4-amino-N,N-dimethylaniline 
• 110-65-6 1,4-dihydroxybut-2-yne 
• 109-97-7 pyrrole 
• 698-70-4 4-Iodo-N,N-dimethylaniline 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 586-77-6 4-bromo-N,N-dimethylaniline 

Relevant academic research and scientific papers

Base-Mediated Borylsilylation/Silylation of Ammonium Salts with Silylborane

This work describes a base-mediated borylsilylation of benzylic ammonium salts to synthesize geminal silylboronates bearing benzylic proton under mild reaction conditions. Deaminative silylation of aryl ammonium salts was also achieved in the presence of

A facile synthesis of diaryl pyrroles led to the discovery of potent colchicine site antimitotic agents

Three different series of cis-restricted analogues of combretastatin A-4 (CA-4), corresponding to thirty-nine molecules that contained a pyrrole nucleus interposed between the two aryl rings, were prepared by a palladium-mediated coupling approach and evaluated for their antiproliferative activity against six human cancer cell lines. In the two series of 1,2-diaryl pyrrole derivatives, results suggested that the presence of the 3′,4′,5′-trimethoxyphenyl moiety at the N-1 position of the pyrrole ring was more favorable for antiproliferative activity. In the series of 3,4-diarylpyrrole analogues, three compounds (11i-k) exhibited maximal antiproliferative activity, showing excellent antiproliferative activity against the CA-4 resistant HT-29 cells. Inhibition of tubulin polymerization of selected 1,2 pyrrole derivatives (9a, 9c, 9o and 10a) was similar to that observed with CA-4, while the isomeric 3,4-pyrrole analogues 11i-k were generally from 1.5- to 2-fold more active than CA-4. Compounds 11j and 11k were the only compounds that showed activity as inhibitors of colchicine binding comparable to that CA-4. Compound 11j had biological properties consistent with its intracellular target being tubulin. This compound was able to block the cell cycle in metaphase and to induce significant apoptosis at a concentration of 25 nM, following the mitochondrial pathway, with low toxicity for normal cells. More importantly, compound 11j exerted activity in vivo superior to that of CA-4P, being able to significantly reduce tumor growth in a syngeneic murine tumor model even at the lower dose tested (5.0 mg/kg).

Sustainable Pathways to Pyrroles through Iron-Catalyzed N-Heterocyclization from Unsaturated Diols and Primary Amines

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.

Electronically Strongly Coupled Divinylheterocyclic-Bridged Diruthenium Complexes

Complexes [{Ru(CO)Cl(PiPr3)2}2(μ-2,5-(CH=CH)2-cC4H2E] (E=NR; R=C6H4-4-NMe2 (10a), C6H4-4-OMe (10b), C6H4-4-Me (10c), C6H5 (10d), C6H4-4-CO2Et (10e), C6H4-4-NO2 (10f), C6H3-3,5-(CF3)2 (10g), CH3 (11); E=O (12), S (13)) are discussed. The solid state structures of four alkynes and two complexes are reported. (Spectro)electrochemical studies show a moderate influence of the nature of the heteroatom and the electron-donating or -withdrawing substituents R in 10a-g on the electrochemical and spectroscopic properties. The CVs display two consecutive one-electron redox events with ΔE°′=350-495 mV. A linear relationship between ΔE°′ and the σp Hammett constant for 10a-f was found. IR, UV/Vis/NIR and EPR studies for 10+-13+ confirm full charge delocalization over the {Ru}CH=CH-heterocycle-CH=CH{Ru} backbone, classifying them as Class III systems according to the Robin and Day classification. DFT-optimized structures of the neutral complexes agree well with the experimental ones and provide insight into the structural consequences of stepwise oxidations.

Designing conducting polymer films for electrochemical energy storage technologies

The search for new materials for electrical energy storage (EES) is one of the most active research areas today. In terms of materials for electrochemical (super)capacitors, most work has focused on high surface area carbons (HSAC) (surface areas in exces

Influencing the electronic interaction in diferrocenyl-1-phenyl-1H-pyrroles

Functionalised diferrocenyl-1-phenyl-1H-pyrroles were synthesised using Negishi C,C cross-coupling reactions. The influence of different substituents at the phenyl moiety on the electronic interaction was studied using electrochemistry (cyclic and square-

Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles

This paper details the copper-catalyzed N-arylation of π-excessive nitrogen heterocycles. The coupling of either aryl iodides or aryl bromides with common nitrogen heterocycles (pyrroles, pyrazoles, indazoles, imidazoles, and triazoles) was successfully performed in good yield with catalysts derived from diamine ligands and CuI. General conditions were found that tolerate functional groups such as aldehydes, ketones, alcohols, primary amines, and nitriles on the aryl halide or heterocycle. Hindered aryl halides or heterocycles were also found to be suitable substrates using the conditions reported herein.