26458-45-7

Upstream product

• 16504-44-2 2H-azirine-2,3-dicarboxylic acid dimethyl ester 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 613-91-2 acetophenone oxime 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 98-86-2 acetophenone 
• 57957-24-1 N-(1-phenylvinyl)acetamide 
• 19433-17-1 acetophenone O-acetyloxime 
• 26704-50-7 dimethyl 2-(((E)-(1-phenylethylidene)amino)oxy)maleate 
• 10341-75-0 (E)-1-phenylethanone oxime 
• 622-79-7 benzyl azide 
• 70-11-1 α-bromoacetophenone 
• 3433-56-5 1-(1-phenylvinyl)pyrrolidine 
• 89649-35-4 2'-Phenyl-2,3,4,5,2',3'-hexahydro-1'H-[1,2']bipyrrolyl-4',5'-dicarboxylic acid dimethyl ester 

Downstream Products

• 1240491-53-5 1-tert-butyl 2,3-dimethyl 5-phenyl-1H-pyrrole-1,2,3-tricarboxylate 

Relevant academic research and scientific papers

Copper-promoted oxidative coupling of enamides and alkynes for the synthesis of substituted pyrroles

An efficient copper-promoted oxidative coupling of enamides with alkynes has been developed for the synthesis of substituted pyrroles. The reaction proceeded through C-H and N-H bond functionalization of enamides under mild conditions.

An efficient synthesis of polysubstituted pyrroles via copper-catalyzed coupling of oxime acetates with dialkyl acetylenedicarboxylates under aerobic conditions

A Cu-catalyzed [3+2]-type condensation reaction of oxime acetates and dialkyl acetylenedicarboxylates that provides highly substituted pyrroles under aerobic conditions is described. The newly formed pyrroles are easily employed for further transformations to prepare pyrrolo[2,1-a]isoquinoline skeletons. The Royal Society of Chemistry 2013.

Development of a gold-multifaceted catalysis approach to the synthesis of highly substituted pyrroles: Mechanistic insights via Huisgen cycloaddition studies

A novel gold-catalyzed method for the regioselective synthesis of highly substituted pyrroles directly from oximes and alkynes was developed via independent optimization of two key steps of the process. Importantly, a cationic gold(I) species was shown to activate multiple steps along the reaction pathway and therefore act as a multifaceted catalyst. Initial gold-promoted addition of the oxime oxygen to the activated alkyne afforded the O-vinyloxime in situ. The O-vinyloxime was subsequently transformed into the pyrrole via a gold-catalyzed tautomerization, [3,3]-sigmatropic rearrangement, and cyclodehydration process. Notably, this method provides a functional group handle in the form of an ester at the 3/4-position for further exploitation. The proposed mechanistic pathway is supported by a novel application of the Huisgen cycloaddition click reaction, which was used to probe the relative stability of substituted O-vinyloximes. The intermediacy of N-alkenylhydroxylamine O-vinyl ethers and imino ketones or imino aldehydes along the reaction pathway were determined by high-temperature 1H, 2H{1H}, and 13C{1H} NMR experiments. X-ray crystallographic evidence was used to further support the mechanistic hypothesis.

Europium(III) triflate-catalyzed Trofimov synthesis of polyfunctionalized pyrroles

The synthesis of polyfunctionalized pyrroles by reaction of a ketoxime with dimethyl acetylenedicarboxylate using europium(III) triflate as the catalyst is described. Copyright

Novel and efficient supramolecular synthesis of pyrroles in the presence of β-cyclodextrin in water

A simple and efficient synthesis of highly substituted pyrroles was achieved in water medium via multi-component strategy, using amine, DMAD/DEAD as well as phenacyl bromide catalyzed by β-CD. Utilizing this protocol various pyrrole derivatives were synthesized in good to excellent yields.

Gold-catalysed rearrangement of O-vinyl oximes for the synthesis of highly substituted pyrroles

O-Vinyl oximes were synthesised from the reaction of oximes with activated alkynes and subsequently rearranged using gold catalysis to afford highly substituted pyrroles in an efficient and regiocontrolled process. Additionally, pyrroles were formed direc

Polyethylene glycol (PEG-400) as an efficient and recyclable reaction medium for one-pot synthesis of polysubstituted pyrroles under catalyst-free conditions

Polyethylene glycol (PEG) was found to be an inexpensive non-toxic and effective medium for the one-pot synthesis of highly functionalized pyrroles. Utilizing this protocol various pyrrole derivatives were synthesized in excellent yields. Environmental acceptability, low cost, high yields, and recyclability of the PEG are the important features of this protocol.

Pyrrole and oligopyrrole synthesis by 1,3-dipolar cycloaddition of azomethine ylides with sulfonyl dipolarophiles

A procedure for the synthesis of functionalized, substituted pyrroles by 1,3-dipolar cycloaddition of azomethine ylides has been developed. This protocol is based on the metal-catalyzed cycloaddition of α-iminoesters with sulfonyl dipolarophiles, followed by the base-promoted elimination of the sulfonyl groups. A wide variety of 2,5-disubstituted and 2,3,5- and 2,4,5trisubstituted pyrroles have been prepared in satisfactory yields from 1,2bis(sulfonyl ethylene), ss-sulfonylenones, and ss- sulfonylacrylates. This method can be applied in an iterative and straightforward manner to the construction of oligopyrroles, from bipyrroles to pentapyrroles. Iterative [n+1] and [n+2] approaches have been devised, the latter involves double 1,3-dipolar cycloaddition from pyrrolylbased bis(iminoesters).

An efficient new method for the synthesis of polysubstituted pyrroles

The three-component reactions of phenacyl bromide or its derivatives, amine, and dialkyl acetylenedicarboxylate in the presence of iron(III) chloride as a catalyst at room temperature afforded polysubstituted pyrroles in high yields. Georg Thieme Verlag Stuttgart.

The Synthesis and Chemistry of Azolenines. Part 2. A General Synthesis of Pyrrole-2-carboxylic Acid Derivatives by the Reaction of 2H-Azirines with Enamines, and the Crystal and Molecular Structure of Ethyl 3-Phenyl-4,5,6,7-tetrahydroindole-2-carboxylate

A new general synthesis of 1H-pyrrole-2-carboxylic acid derivatives is described.Reaction between appropriately substituted 2H-azirines and enamines gives a mixture of 2,3- and 3,4-dihydropyrroles, which on acid treatment yields the title compounds in mod