3274-65-5

Upstream product

• 141-97-9 ethyl acetoacetate 
• 108-86-1 bromobenzene 
• 68999-91-7 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylic acid 2-benzyl ester 4-ethyl ester 
• 62664-59-9 ethyl 2-acetyl-3-methyl-4-oxo-4-phenylbutanoate 
• 111400-49-8 2-Benzoyl-2-methyl-4-oxo-pentanoic acid ethyl ester 
• 111400-61-4 3,5-Dimethyl-2-phenyl-3H-pyrrole-3-carboxylic acid ethyl ester 
• 111400-65-8 3-Methyl-5-methylene-2-phenyl-4,5-dihydro-3H-pyrrole-3-carboxylic acid ethyl ester 

Downstream Products

• 881675-24-7 ethyl 2,4-dimethyl-5-phenyl-1-(phenylsulfonyl)-1H-pyrrole-3-carboxylate 
• 257862-99-0 C₁₃H₁₃NO₂ 

Relevant academic research and scientific papers

Decarboxylative arylation of substituted pyrroles N -protected with 2-(trimethylsilyl)ethoxymethyl (SEM)

Palladium-catalyzed decarboxylative arylation is reported using pyrroles N-protected with the 2-(trimethylsilyl)ethoxymethyl (SEM) group and featuring 2-, 3-, and 4-substituents about the pyrrolic framework. In contrast to N-protected pyrroles previously

Proton pump inhibitors

A proton pump inhibitor containing a compound represented by the formula (I) wherein X and Y are the same or different and each is a bond or a spacer having 1 to 20 carbon atoms in the main chain, R 1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, R 2 , R 3 and R 4 are the same or different and each is a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted thienyl group, an optionally substituted benzo[b]thienyl group, an optionally substituted furyl group, an optionally substituted pyridyl group, an optionally substituted pyrazolyl group, an optionally substituted pyrimidinyl group, an acyl group, a halogen atom, a cyano group or a nitro group, R 5 and R 6 are the same or different and each is a hydrogen atom or an optionally substituted hydrocarbon group, which has a superior proton pump action and shows an antiulcer activity and the like after conversion to a proton pump inhibitor in the body, or a salt thereof. or a prodrug thereof is provided.

Further optimization of novel pyrrole 3-carboxamides for targeting serotonin 5-HT2A, 5-HT2C, and the serotonin transporter as a potential antidepressant

In the continuing search for novel compounds targeting serotonin 5-HT 2A, 5-HT2C, and serotonin transporter, new arylpiperazine-containing pyrrole 3-carboxamide derivatives were synthesized and evaluated. Based on the lead reported previously, structural modifications regarding N-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propyl)-1,2-dimethyl-5- phenyl-1H-pyrrole-3-carboxamide 5, were accomplished for improvements in not only binding affinity against serotonin receptors and transporter, but also in hERG channel inhibition. Along the line, both the forced swimming tests and spontaneous locomotor activity tests were performed to distinguish between antidepressant activity and false positive results. As potential antidepressant agents, both 2,4-dimethyl-5-phenyl-1H-pyrrole-3-carboxamide and 5-tert-butyl-2-methyl-1H-pyrrole-3-carboxamide derivatives exhibited favorable in vitro and in vivo activities, warranting further investigation around these scaffolds.

Mn(III)-catalyzed synthesis of pyrroles from vinyl azides and 1,3-dicarbonyl compounds

(Chemical Equation Presented) Polysubstituted N-H pyrroles with a wide variety of substituents were prepared from vinyl azides and 1,3-dicarbonyl compounds by using Mn(III) complexes as catalysts.

PROTON PUMP INHIBITORS

A proton pump inhibitor containing a compound represented by the formula (I) wherein X and Y are the same or different and each is a bond or a spacer having 1 to 20 carbon atoms in the main chain, R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, R2, R3 and R4 are the same or different and each is a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted thienyl group, an optionally substituted benzo[b]thienyl group, an optionally substituted furyl group, an optionally substituted pyridyl group, an optionally substituted pyrazolyl group, an optionally substituted pyrimidinyl group, an acyl group, a halogen atom, a cyano group or a nitro group, R5 and R6 are the same or different and each is a hydrogen atom or an optionally substituted hydrocarbon group, which has a superior proton pump action and shows an antiulcer activity and the like after conversion to a proton pump inhibitor in the body, or a salt thereof. or a prodrug thereof is provided.

THE SYNTHESIS AND CHEMISTRY OF AZOLENINES. PART 18. PREPARATION OF 3-ETHOXYCARBONYL-3H-PYRROLES VIA THE PAAL-KNORR REACTION, AND SIGMATROPIC REARRANGEMENTS INVOLVING COMPETITIVE ESTER MIGRATIONS TO C-2, C-4 AND N.

3H-Pyrrole-3-carboxylic esters (4) have been prepared, in some cases together with isomers (5) and (6) having exocyclic double bonds, by cyclization of suitably substituted 2-ethoxycarbonyl-1,4-diketones (1) with liquid ammonia, followed by dehydration of the isolable 2-hydroxy-3,4-dihydro-2H-pyrrole intermediates (2) and (3) with aluminia in boiling solvents.Prolonged heating in toluene or p-xylene converts the 3H-pyrroles (4) quantitatively into isomeric 4-esters (11) and N-esters (13) of 1H-pyrroles via competitive sigmatropic rearrangements.Isolable intermediate 2H-pyrrole-2-carboxylic esters (12) are converted similarly into the same products, under the same conditions.Detection of 3H-pyrroles (4) as intermediates in the latter reaction demonstrates for the first time the reversibility of the thermal 2H-pyrrole to 3H-pyrrole interconversion.

THERMAL REARRANGEMENT OF 3H-PYRROLES BY COMPETITIVE -SIGMATROPIC SHIFTS, AND THE REVERSIBILITY OF THE 3H- TO 2H-PYRROLE INTERCONVERSION

3-Ethoxycarbonyl-3H-pyrroles are converted via thermal -ester shifts to the isomeric 1H-pyrrole-4- and N-esters.Isolable intermediate 2H-pyrroles are converted into the same products, and also into the 3H-pyroles, demonstrating conclusively the reversibility of the 3H- to 2H-pyrrole interconversion.