140137-33-3

Upstream product

• 110-13-4 2,5-hexanedione 
• 95-68-1 2,4-Xylidine 
• 109-49-9 5-Hexen-2-one 

Downstream Products

• 328028-87-1 C₁₅H₁₇NO 
• 471885-11-7 C₂₀H₂₃N₃OS 

Relevant academic research and scientific papers

Microwave assisted synthesis of pyrroles

The synthesis of pyrroles by reaction of hexane-2,5-dione with primary amines has been shown to occur in less than 2 minutes under microwave activation.

Synthesis of Pyrrole Derivatives Promoted by Fe(ClO4)3/SiO2 as an Environmentally Friendly Catalyst

N-Substituted pyrroles have been prepared in high isolated yields (702-99%) by the reaction of hexane-2,5-dione with amines or diamines in the presence of Fe(ClO4)3/SiO2 at ambient temperature under solvent-free conditions. The experimental procedure involves simple operations, and the products are readily separated by short column chromatography. The same reaction of hexane-2,5-dione with amines containing electron-acceptor substituents, such as 4-nitroaniline, resulted in fair yields of pyrrole derivatives.

Synthesis of Fe3O4@L-proline@SO3H as a novel and reusable acidic magnetic nanocatalyst and its application for the synthesis of N-substituted pyrroles at room temperature under ultrasonic irradiation and without solvent

N-Substituted pyrroles have been prepared in high isolated yields (65–90%) by the reaction of hexane-2,5-dione with amines or diamines in the presence of Fe3O4@L-proline@SO3H at ambient temperature under ultrasonic irradiation and without solvent. The experimental procedure involves simple operations, and the products are readily separated by external magnet. The same reaction of hexane-2,5-dione with amines containing electron-acceptor substituents, such as 4-nitroaniline, resulted in fair yields of pyrrole derivatives.

Naturally occurring organic acids for organocatalytic synthesis of pyrroles via Paal–Knorr reaction

Abstract: In this study, common naturally occurring organic acids, namely oxalic, malonic, succinic, tartaric and citric acid (as safe, inexpensive, and biodegradable organocatalysts), have been employed for Paal–Knorr pyrrole synthesis. The organocatalyzed reaction proved to be effective in ethanol at 60?°C. However, the reaction rate is mainly dominated by the nature and position of functional groups on the aromatic ring of substrate. This metal-free procedure tolerates a series of functional groups and should be considered as an asset to the pharmaceutical industry since no metal contamination could take place during the synthesis of pyrrole scaffolds. Graphic abstract: [Figure not available: see fulltext.].

Efficient synthesis of substituted pyrroles through Pd(OCOCF3)2-catalyzed reaction of 5-hexen-2-one with primary amines

An efficient and facile Pd(OCOCF3)2-catalyzed one-pot cascade protocol has been developed for the synthesis of multiple substituted pyrroles in good to excellent yields. Unlike the reported method starting from the 2-alkenal-1,3-carbonyl compounds, the process utilizes the less reactive 5-hexen-2-one and the method has great potential as a complement to the current developed methods.

The application of iron (III) phosphate in the synthesis of N-substituted pyrroles

A variety of N-substituted pyrroles have been prepared by reacting 2,5-hexadione with amines or diamines in the presence of iron (III) phosphate at room temperature under solvent-free conditions. The experiment protocol features simple operations, and the products are isolated in high yields (88-99%).

Discovery, synthesis and SAR analysis of novel selective small molecule S1P4-R agonists based on a (2Z,5Z)-5-((pyrrol-3-yl)methylene)-3- alkyl-2-(alkylimino)thiazolidin-4-one chemotype

High affinity and selective S1P4 receptor (S1P4-R) small molecule agonists may be important proof-of-principle tools used to clarify the receptor biological function and effects to assess the therapeutic potential of the S1P4-R in diverse disease areas including treatment of viral infections and thrombocytopenia. A high-throughput screening campaign of the Molecular Libraries-Small Molecule Repository was carried out by our laboratories and identified (2Z,5Z)-5-((1-(2-fluorophenyl)-2,5-dimethyl-1H- pyrrol-3-yl)methylene)-3-methyl-2-(methylimino) thiazolidin-4-one as a promising S1P4-R agonist hit distinct from literature S1P4-R modulators. Rational chemical modifications of the hit allowed the identification of a promising lead molecule with low nanomolar S1P4-R agonist activity and exquisite selectivity over the other S1P 1-3,5-Rs family members. The lead molecule herein disclosed constitutes a valuable pharmacological tool to explore the effects of the S1P4-R signaling cascade and elucidate the molecular basis of the receptor function.