128259-47-2

Usage

Uses

Used in Pharmaceutical Industry:
1-Benzylpyrrole-3-carboxylic acid ethyl ester is used as a reactant in the synthesis of various heterocyclic compounds, such as furo-, thieno-, and pyrroloazepines. These compounds have potential applications in the development of new pharmaceuticals, particularly in the treatment of various diseases and disorders.
Used in Chemical Research:
In the field of chemical research, 1-Benzylpyrrole-3-carboxylic acid ethyl ester serves as a valuable intermediate for the preparation of complex organic molecules. Its unique structure allows for further functionalization and modification, making it a versatile building block for the synthesis of novel compounds with potential applications in various industries.
Used in Material Science:
1-Benzylpyrrole-3-carboxylic acid ethyl ester can also be utilized in the development of new materials with specific properties. Its ability to form stable complexes and interact with other molecules makes it a promising candidate for use in the creation of advanced materials with applications in areas such as electronics, coatings, and adhesives.

Synthesis Reference(s)

Synthesis, p. 753, 1990 DOI: 10.1055/s-1990-27004

InChI:InChI=1/C14H15NO2/c1-2-17-14(16)13-8-9-15(11-13)10-12-6-4-3-5-7-12/h3-9,11H,2,10H2,1H3

Upstream product

• 5747-92-2 1-benzyl-3-carboethoxypyrrolidine 
• 37964-17-3 pyrrole-3-carboxylic acid ethyl ester 
• 100-39-0 benzyl bromide 
• 29897-82-3 N-benzylpyrrolidine 
• 140-88-5 ethyl acrylate 
• 3783-61-7 diethyl 2-azabutane-1,4-dicarboxylate 
• 795-18-6 3-(benzyl-ethoxy-carbonylmethyl-amino)-propionic acid ethyl ester 
• 1027-35-6 1-Benzyl-4-oxo-pyrrolidine-3-carboxylic Acid Ethyl Ester 
• 100-46-9 benzylamine 
• 128259-46-1 ethyl 1-benzyl-2,5-dihydro-1H-pyrrole-3-carboxylate 

Downstream Products

• 18159-17-6 1-benzyl-1H-pyrrole-3-carboxylic acid 
• 56559-61-6 ethyl 1-benzyl-1H-indole-3-carboxylate 
• 84092-58-0 (1-benzyl-1H-pyrrol-3-yl)methanol 

Relevant academic research and scientific papers

Direct synthesis of: N -aryl/alkyl 3-carbonylpyrroles from the Morita-Baylis-Hillman acetate of 2,2-dimethoxyacetaldehyde and a primary amine

N-Aryl/alkyl 3-carbonylpyrroles are ubiquitous in compounds of biological and material significance, whereas their synthesis traditionally requires a multistep protocol. Herein a kalinite catalyzed direct synthesis of N-substituted 3-carbonylpyrroles from a 2,2-dimethoxyacetaldehyde derived Morita-Baylis-Hillman acetate and a primary amine in ethanol is developed. This reaction is scalable and also applicable to the synthesis of JMH-030, JMC-2004 and other bioactive compounds. This journal is

An aza-nucleoside, fragment-like inhibitor of the DNA repair enzyme alkyladenine glycosylase (AAG)

The DNA repair enzyme AAG has been shown in mice to promote tissue necrosis in response to ischaemic reperfusion or treatment with alkylating agents. A chemical probe inhibitor is required for investigations of the biological mechanism causing this phenomenon and as a lead for drugs that are potentially protective against tissue damage from organ failure and transplantation, and alkylative chemotherapy. Herein, we describe the rationale behind the choice of arylmethylpyrrolidines as appropriate aza-nucleoside mimics for an inhibitor followed by their synthesis and the first use of a microplate-based assay for quantification of their inhibition of AAG. We finally report the discovery of an imidazol-4-ylmethylpyrrolidine as a fragment-sized, weak inhibitor of AAG.

Br?nsted Acid Catalyzed Cyclization of Aminodiazoesters with Aldehydes to 3a'Carboxylatea'Na'Heterocycles

A Br?nsted acid catalyzed cyclization of aminodiazoesters with aldehydes is described. This reaction features broad substrate generality and functional group compatibility, affording a wide range of 5a'7-membered 3-carboxylate-N-heterocycles containing different functional groups. The title products are able to be further elaborated through simple functional group transformations to produce synthetically useful N-heterocycles.

C(sp3)-H dehydrogenation and C(sp2)-H alkoxy carbonylation of inactivated cyclic amines towards functionalized N-heterocycles

A novel and efficient synthesis of tetrahydropyridine (THP)-, dihydropyrrole (DHP)-, or tetrahydroazepine (THA)-3-carboxylates via cascade reactions of inactivated cyclic amines with CO and alcohols is presented. To our knowledge, this should be the first

Synthetic method of pyrrole-3-formic acid ester compound

The invention discloses a synthetic method of a pyrrole-3-formic acid ester compound and belongs to the field of organic synthesis technology. The main point of the scheme is as follows: according to the synthetic method of the pyrrole-3-formic acid ester compound, a dihydropyrrole-3-formic acid ester compound is dissolved in a solvent, and in the presence of an oxidizing agent, reacts at the temperature of 60-120 DEG C so as to prepare the pyrrole-3-formic acid ester compound. In comparison with the prior art, the invention has the following advantages: (1) by the adoption of one-step reaction, waste emission is decreased and environmental burden is reduced; (2) by using oxygen or air as the oxidizing agent, the condition is green and environment-friendly; (3) the reaction is carried out at the temperature of minus 120 DEG C, condition is mild, and operation is simple; (4) the application range of a substrate is wide; and (5) atom economy of the reaction is high.

Synthesis of novel furo-, thieno-, and pyrroloazepines

The synthesis of novel furo-, thieno-, and pyrroloazepine compounds, using the oxidative radical alkylation of three five-membered heterocyclic 3-acetic acid derivatives, is described. The bicyclic systems were obtained, via a small number of steps, directly from commercially available materials. Georg Thieme Verlag Stuttgart New York.

Pyrroloazepine derivatives

A method for treating a circulatory disease or condition in a mammal, which entails administering to the mammal an effective amount of a compound of the formula (I) or a pharmaceutically acceptable salt thereof: wherein the ring P represented by ?is a pyrrole ring having the following structure: wherein R1represents C1-C8alkyl, C3-C8cycloalkyl, C4-C8cycloalkyl-alkyl, C6-C14aryl or C7-C22aralkyl, which are optionally substituted; and R2represents H or C1-C8alkyl, which is optionally substituted; the dashed line indicates the presence or absence of a bond; and, when the bond is present, Z2is not present and Z1represents H, but, when the bond is absent, Z1and Z2are both H; Z1represents H and Z2represents a group OR3, in which R3represents H, C1-C8alkyl, or C7-C22aralkyl, which are optionally substituted; Z1and Z2both represent groups SR4, in which R4represents C1-C8alkyl or C7-C22aralkyl, which are optionally substituted; or Z1and Z2are combined together to represent O, a group NOR5, in which R5represents H, or C1-C8alkyl or C2-C3alkylenedithio, which are optionally substituted; A represents alkylene, alkenylene or alkynylene; and Y represents a group in which W is CH, C═ or N, m is for 0 or 1, n is for 1, 2 or 3, G is O, S, C═O, sulfinyl, sulfonyl, alkylene, alkenylene or acetal; E1and E2is H or C1-C8alkyl; and D represents an aromatic hydrocarbon or an aromatic heterocyclic ring. The compound (I) has strong serotonin-2 receptor antagonistic action and low toxicity and less side effects, and is therapeutically useful in the treatment of circulatory diseases and/or conditions related thereto.

Pyrroloazepine derivatives

A pyrroloazepine compound having the following formula (I): wherein the ring P represented by STR1 is a pyrrole ring having the following structure: STR2 wherein R1 represents C1 -C8 alkyl, C3 -C8 cycloalkyl, C4 -C8 cycloalkyl-alkyl, C6 -C14 aryl or C7 -C22 aralkyl, which are optionally substituted; and R2 represents H or C1 -C8 alkyl, which is optionally substituted; the dashed line indicates the presence or absence of a bond; and, when the bond is present, Z2 is not present and Z1 represents H, but, when the bond is absent, Z1 and Z2 are both H; Z1 represents H and Z2 represents a group OR3, in which R3 represents H, C1 -C8 alkyl, or C7 -C22 aralkyl, which are optionally substituted; Z1 and Z2 both represent groups SR4, in which R4 represents C1 -C8 alkyl or C7 -C22 aralkyl, which are optionally substituted; or Z1 and Z2 are combined together to represent O, a group NOR5, in which R5 represents H, or C1 -C8 alkyl or C2 -C3 alkylenedithio, which are optionally substituted; A represents alkylene, alkenylene or alkynylene; and Y represents a group in which W is CH, C= or N, m is for 0 or 1, n is for 1, 2 or 3, G is O, S, C=O, sulfinyl, sulfonyl, alkylene, alkenylene or acetal; E1 and E2 is H or C1 -C8 alkyl; and D represents an aromatic hydrocarbon or an aromatic heterocyclic ring. The compound (I) has strong serotonin-2 receptor antagonistic action and low toxicity and less side effects, and is therapeutically useful in the treatment of circulatory diseases and/or conditions related thereto.

Process for preparing 1-substituted pyrrole-3-carboxylic acid derivatives

A simple and industrially viable process for preparing a 1-substituted pyrrole-3-carboxylic acid derivative of formula (I) is provided. The process comprises reacting a compound of formula (II), a compound of formula (III), and an acid anhydride according

Process for preparing 1-substituted pyrrole-3-carboxylic acid derivatives

A simple and industrially viable process for preparing a 1-substituted pyrrole-3-carboxylic acid derivative of formula (I) is provided. The process comprises reacting a compound of formula (II), a compound of formula (III), and an acid anhydride according