53646-85-8

Upstream product

• 149217-19-6 2-chloro-1,4-diphenylpyrrole 
• 10034-85-2 hydrogen iodide 
• 92500-59-9 α-(2,2-diethoxyethyl)benzyl cyanide 
• 140-29-4 phenylacetonitrile 
• 591-50-4 iodobenzene 
• 103204-12-2 1-phenyl-2,5-dihydro-1H-pyrrole 
• 62-53-3 aniline 
• 635-90-5 1-phenylpyrrole 
• 6006-81-1 3-hydroxy-2-phenylpropene 
• 56865-72-6 2-Phenyl-3-(phenylamino)-1-propene 
• 4411-89-6 (E/Z)-2-phenylcrotonaldehyde 
• 98-80-6 phenylboronic acid 
• 939-21-9 3-phenyl-4-pentenal 
• 80816-24-6 (E)-[3-(vinyloxy)prop-1-en-1-yl]benzene 

Relevant academic research and scientific papers

Iron-catalyzed sustainable synthesis of pyrrole

Efficient, sustainable, highly regiospecific substituted pyrroles were synthesized using a well-defined, air stable, molecular iron(0) complex. The developed methodology is broadly applicable and tolerates a variety of functional groups. C-2, C-3, and C-2 & C-4 substituted pyrroles were synthesized in good yield. Symmetrical bis-pyrroles were accessible for the first time using an iron catalyst. On the basis of the experimental observation, we propose that the reaction proceeds through a hydrogen autotransfer process followed by second oxidation/ intramolecular dehydrative condensation to provide the pyrrole.

Synthesis of 1,3- and 1,2,3-functionalized pyrroles via Ir(I)-catalyzed vinylation of allyl alcohols

[Figure not available: see fulltext.] An efficient method for the preparation of 1,3-disubstituted and 1,2,3-trisubstituted pyrroles was developed through a sequence involving O-vinylation of allyl alcohols followed by Claisen rearrangement and further ozonolysis, concurring in a Paal–Knorr reaction with primary amines. Hg(II) and Ir(I) catalysts and different vinylating reagents were tested. The best results were consistently obtained with the [Ir(cod)Cl]2–vinyl acetate system. The featured methodology gives access to functionalized pyrroles in overall good yields, whose chemical architecture may awake interest for assorted applications.

Synthesis of Multisubstituted Pyrroles from Enolizable Aldehydes and Primary Amines Promoted by Iodine

1,2,4-Trisubstituted pyrroles were synthesized from enolizable aliphatic aldehydes and primary aliphatic amines by using iodine as the dual Lewis acid/mild oxidant. In the presence of 3.0 equiv of TBHP, enolizable α,β-unsaturated aldehyde, for example, co

Synthetic method of 3-aryl substituted pyrrole compound

The invention discloses a synthetic method of a 3-aryl substituted pyrrole compound, and belongs to the technical field of organic synthesis. The method includes the steps: adding N-substituted piperidine 1 into a solvent; performing heating reaction in o

A General Route to β-Substituted Pyrroles by Transition-Metal Catalysis

An atom-efficient route to pyrroles substituted in the β-position has been achieved in four high yielding steps by a combination of Pd, Ru, and Fe catalysis with only water and ethene as side-products. The reaction is general and gives pyrroles substitute

β-selective C-H arylation of pyrroles leading to concise syntheses of lamellarins C and I

The first general β-selective C-H arylation of pyrroles has been developed by using a rhodium catalyst. This C-H arylation reaction, which is retrosynthetically straightforward but results in unusual regioselectivity, could result in de novo syntheses of

Multistep reactions using microreactor chemistry

A microflow system for the investigation of multistep syntheses involving Pd-catalysed Heck reactions and Ru-catalysed ring-closing metathesis is described. A successful provision of reagent and catalyst delivery in a consecutive fashion allowed control over reaction parameters leading to fast optimisation. The performance of Heck reactions in multistep procedures was not as successful as in the single step coupling, whereas the ring-closing metathesis proved to be successful in the production of the desired compounds for further functionalisation. ARKAT-USA, Inc.

A new synthesis of monosubstituted succinaldehydes and 3-substituted pyrroles from acetonitriles. Formal synthesis of 2,3-dihydro-7-methyl-2H-pyrrolizidin-1-one (Danaidone), a semiochemical of Danaid butterflies

A convenient and versatile synthesis of monosubstituted succinaldehydes and 3-substituted pyrroles from acetonitriles was devised. The methodology was applied to the preparation of 9, the penultimate intermediate in the Meinwald and Meinwald synthesis of Danaidone.12 Copyright

Thermal rearrangement of N-alkyl-, and N-aryl-(2,2-dihalo-1-phenylcyclopropyl)methyleneamines to 1-alkyl-, and 1-aryl-2 (or 3)-halo-4-phenylpyrroles

The thermolysis of N-t-alkyl-, and N-aryl-(2,2-dichlorocyclopropyl)methyleneamines yielded directly 1-t-alkyl, and 1-aryl-3-chloropyrroles as the major products along with a slight amount of the 2-chloro isomers. The transformation to the 3-chloropyrroles was enhanced in polar solvents. But basic additives directed the thermal rearrangement into the 1,2-bond cleavage of the cyclopropane ring, leading to the 2-chloropyrroles. On the other hand, (difluorocyclopropyl)methyleneamines were pyrolyzed exclusively to 3-fluoropyrroles under 1,3-bond cleavage. The ionic mechanism involving a heterolytic dissociation of chlorine atom under 1,3-bond scission of the cyclopropane ring is proposed for the rearrangement to 3-chloropyrroles, while a homolytic cleavage pathway is proposed for 3-fluoropyrroles. The present thermolysis supplies a unique preparative tool for 2-, and 3-halo-4-phenylpyrrole derivatives.