62128-32-9

Upstream product

• 96-54-8 N-Methylpyrrole 
• 14062-80-7 N,N-dimethyl-4-chlorobenzamide 
• 112925-42-5 2-[2-(4-Chloro-phenyl)-benzo[1,3]oxathiol-2-yl]-1-methyl-1H-pyrrole 
• 637-87-6 1-Chloro-4-iodobenzene 
• 201230-82-2 carbon monoxide 
• 58948-38-2 2-(4-Chlorophenyl)-1,3-benzoxathiolium tetrafluoroborate 
• 122-01-0 4-chloro-benzoyl chloride 

Downstream Products

• 62128-44-3 N-methyl-3-(4-chlorobenzoyl)-1H-pyrrole 
• 76024-67-4 2,4-bis(4-chlorobenzoyl)-1-methylpyrrole 
• 157847-06-8 2-chloro-1-[5-(4-chlorobenzoyl)-1-methyl-1-H-pyrrol-3-yl]-ethanone 
• 157847-13-7 4-chloro-1-[5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]-butanone 
• 157847-44-4 1-[5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]-2-(1-pyrrolidinyl)ethanone 
• 560088-42-8 [5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]pyridin-4-ylmethanone 

Relevant academic research and scientific papers

An Electrophilic Approach to the Palladium-Catalyzed Carbonylative C-H Functionalization of Heterocycles

A palladium-catalyzed approach to intermolecular carbonylative C-H functionalization is described. This transformation is mediated by PtBu3-coordinated palladium catalyst and allows the derivatization of a diverse range of heterocycles, including pyrroles, indoles, imidazoles, benzoxazoles, and furans. Preliminary studies suggest that this reaction may proceed via the catalytic formation of highly electrophilic intermediates. Overall, this provides with an atom-economical and general synthetic route to generate aryl-(hetero)aryl ketones using stable reagents (aryl iodides and CO) and without the typical need to exploit pre-metalated heterocycles in carbonylative coupling chemistry.

Solvent free synthesis of 2-acylpyrroles and its derivatives catalysed by reuseable zinc oxide

A highly efficient procedure for preparing 2-acylpyrroles and its derivatives is described. The products were obtained through regioselective Friedel-Crafts reactions of pyrroles and its derivatives with alkyl or aryl acid chlorides catalysed by zinc oxide under solvent-free conditions. This method has the advantages of green chemistry, operational simplicity, solvent-free conditions, and recoverable catalyst.

Aroyl(aminoacyl)pyrroles, a new class of anticonvulsant agents

2-Aroyl-4-(ω-aminoacyl)- (4) and 4-aroyl-2-(ω-aminoacyl)pyrroles (9) represent a new, structurally novel class of anticonvulsant agents. Compounds of type 4 were prepared by Friedel-Crafts acylation of a 2-aroylpyrrole with an ω-chloroacyl chloride followed by displacement of the chloro group by a primary or secondary amine. Compounds of type 9 were prepared by Friedel- Crafts aroylation of a 2-(ω-chloroacyl)pyrrole followed by displacement by an amine. These compounds were active in the mouse and rat maximal electroshock tests but not in the mouse metrazole test. The lead compound, RWJ-37868, 2-(4-chlorobenzoyl)-4-(1-piperidinyl-acetyl)-1,3,5- trimethylpyrrole (4d), showed potency and therapeutic index comparable to those of phenytoin and carbamazepine and greater than those of sodium valproate. This compound blocked bicuculline induced seizures, did not elevate seizure threshold following iv infusion of metrazole, and blocked influx of Ca2+ ions into cerebellar granule cells induced by K+ or veratridine.

Acylation of Pyrrole and N-Methylpyrrole with 1,3-Benzoxathiolium Tetrafluroborates. A High-Yield Method for the Synthesis of Diacylpyrroles

2-Substituted 1,3-benzoxathiolium tetrafluoroborates (I) were used as masked acylating agents for pyrrole and N-methylpyrrole.The reactions on pyrrole (II) were regiospecific, and according to the molar ratio of the reagents (I:II = 1:3 or 2.5-3:1), 2-acylpyrroles were obtained in moderate to good yields (38-82percent) and 2,5-diacylpyrroles were obtained in excellent yields (in most cases, quantitative).The reactions on N-methylpyrrole (III) were not regioselective, and both α- and β-positions were attacked.So, depending on the molar ratio of the reagents (I:III = 1:3 or 2,5-3:1), 2- and 3-acyl-N-methylpyrroles (9-51percent and 27-68percent yields, respectively) and 2,4- and 2,5-diacyl-N-methylpyrroles (60-93percent and 17-40percent, respectively) were obtained.A very interesting feature of the new method is the possibility of introducing two identical or different acyl groups in the pyrrole ring under mild conditions. 1H and 13C NMR spectra of all the new compounds and IR spectra, recorded in the gas phase, of 2- and 3-acylpyrroles and of 2,4- and 2,5-diacylpyrroles are reported.

Acid-Mediated Rearrangement of Acylpyrroles

N-Alkyl-2-acylpyrroles are converted by strong anhydrous acid to 1-alkyl-3-acylpyrroles.An equilibrium mixture of 2- and 3-acylpyrrole is produced by treatment of a 2- or 3-acyl NH pyrrole with acid.Pyrrolecarboxaldehydes similarly afford isomeric mixtures.A cross-ring migration, 7->8, is observed when the adjacent position is blocked.The mechanism of acid-mediated rearrangement of acylpyrroles is discussed.