59194-30-8

Upstream product

• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 6641-64-1 4,5-dichloro-2-nitroaniline 
• 6972-71-0 4,5-dimethyl-2-nitrobenzenamine 

Downstream Products

• 210222-89-2 7,8-Dichloro-4-((E)-styryl)-pyrrolo[1,2-a]quinoxaline-1-carbaldehyde 
• 210222-84-7 N-(4,5-dichloro-2-pyrrol-1-yl-phenyl)-3-phenylacrylamide 
• 210222-86-9 7,8-Dichloro-4-phenyl-pyrrolo[1,2-a]quinoxaline-1-carbaldehyde 
• 210222-82-5 N-(4,5-dichloro-2-pyrrol-1-yl-phenyl)benzamide 
• 210222-81-4 7,8-Dichloro-4-((E)-styryl)-pyrrolo[1,2-a]quinoxaline 
• 210222-79-0 7,8-dichloro-4-phenylpyrrolo[1,2-a]quinoxaline 
• 210222-76-7 2-chloro-N-(4,5-dichloro-2-pyrrol-1-ylphenyl)acetamide 
• 59194-31-9 4,5–dichloro–2–(1H–pyrrol–1–yl)aniline 

Relevant academic research and scientific papers

Simple and green synthesis of benzimidazoles and pyrrolo[1,2-: A] quinoxalines via Mamedov heterocycle rearrangement

A method for the synthesis of coupling compounds of benzimidazoles and pyrrolo[1,2-a]quinoxalines via Mamedov Heterocycle Rearrangement is reported here. This method was conducted at room temperature and only solvent (HOAc) was required. A series of 4-(1H-benzo[d]imidazol-2-yl)pyrrolo[1,2-a]quinoxaline derivatives were obtained in moderate to good yields.

Synthesis of oxazolidinones through ring-opening and annulation of vinylene carbonate with 2-pyrrolyl/indolylanilines under Rh(iii) catalysis

Herein, we have developed a rhodium-catalyzed C-H functionalization and subsequent intramolecular ring-opening/cyclization of vinylene carbonate with 2-pyrrolyl/indolylanilines, which leads to oxazolidinones in moderate to good yields. In this transformation, vinylene carbonate only eliminates one oxygen atom rather than -CO3 or CO2. Furthermore, some control experiments are conducted to elucidate the reaction mechanism. This journal is

Pyrrolo[1,2-a]quinoxalines: Insulin Mimetics that Exhibit Potent and Selective Inhibition against Protein Tyrosine Phosphatase 1B

PTP1B dephosphorylates insulin receptor and substrates to modulate glucose metabolism. This enzyme is a validated therapeutic target for type 2 diabetes, but no current drug candidates have completed clinical trials. Pyrrolo[1,2-a]quinoxalines substituted at positions C1–C4 and/or C7–C8 were found to be nontoxic to cells and good inhibitors in the low- to sub-micromolar range, with the 4-benzyl derivative being the most potent inhibitor (0.24 μm). Some analogues bearing chlorine atoms at C7 and/or C8 kept potency and showed good selectivity compared to TCPTP (selectivity index '40). The most potent inhibitors behaved as insulin mimetics by increasing glucose uptake. The 4-benzyl derivative inhibited insulin receptor substrate 1 and AKT phosphorylation. Molecular docking and molecular dynamics simulations supported a putative binding mode for these compounds to the allosteric α3/α6/α7 pocket, but inconsistent results in enzyme inhibition kinetics were obtained due to the high tendency of these inhibitors to form stable aggregates. Computational calculations supported the druggability of inhibitors.

Terminal methyl as a one-carbon synthon: Synthesis of quinoxaline derivatives: Via radical-type transformation

An iron-promoted method for the construction of pyrrolo[1,2-a]quinoxaline derivatives has been developed. Ferric chloride served as a promoter and as a Lewis acid in the reaction. Solvents provided the corresponding carbon sources simultaneously. The majority of solvents with terminal methyl groups, including ethers, amines and dimethyl sulfoxide, were reactive in the synthesis of quinoxaline derivatives at a certain yield via C-H(sp3) amination/C-O or C-N (C-S) cleavage. This method was applicable to a wide range of pyrrolo[1,2-a]quinoxaline and indolo[1,2-a]quinazoline substrates.

Copper-Catalyzed Synthesis of Alkyl-Substituted Pyrrolo[1,2- a ]quinoxalines from 2-(1 H -Pyrrol-1-yl)anilines and Alkylboronic Acids

A radical pathway for the construction of pyrrolo[1,2- a ]quinoxalines by using 2-(1 H -pyrrol-1-yl)anilines and alkylboronic acids has been developed. Features of this process include Cu catalysis, readily accessible starting materials, and simple operat

TFAA-Catalyzed Annulation Synthesis of Spiro Pyrrolo[1,2-a]quinoxaline Derivatives from 1-(2-Aminophenyl)pyrroles and Benzoquinones/Ketones

A metal-free trifluorosulfonate anhydride (TFAA)-catalyzed strategy for the synthesis of spiro pyrrolo[1,2-a]quinoxalines from 1-(2-aminophenyl)pyrroles and benzoquinones/ketones has been developed. With this general method, spiro pyrrolo[1,2-a]quinoxalin

Copper-catalyzed tandem aerobic oxidative cyclization for the synthesis of 4-cyanoalkylpyrrolo[1,2-a]quinoxalines from 1-(2-aminophenyl)pyrroles and cyclobutanone oxime esters

A copper-catalyzed tandem ring-opening/cyclization reaction for the synthesis of 4-cyanoalkylpyrrolo[1,2-a]quinoxalines from 1-(2-aminophenyl)pyrroles and cyclobutanone oxime esters has been developed. This reaction involves C-C bond cleavage and C-C and C-N bond constructions with good functional group tolerance. A wide range of products are obtained in moderate to good yields under mild conditions.

FeCl3-Catalyzed synthesis of pyrrolo[1,2-: A] quinoxaline derivatives from 1-(2-aminophenyl)pyrroles through annulation and cleavage of cyclic ethers

A straightforward Fe-catalyzed method for the synthesis of pyrrolo[1,2-a]quinoxalines from 1-(2-aminophenyl)pyrroles and cyclic ethers, which includes functionalization of C(sp3)-H bonds and the construction of C-C and C-N bonds, has been devel

Pyrroloquinoxaline derivatives as high-affinity and selective 5-HT3 receptor agonists: Synthesis, further structure-activity relationships, and biological studies

The synthesis, pharmacological evaluation, and structure-activity relationships (SARs) of a series of novel pyrroloquinoxalines and heteroaromatic-related derivatives are described. The new pyrroloquinoxaline- related ligands were tested in rat cortex, a tissue expressing high density of 5-HT3 receptors, and on NG108-15 cells and exhibited IC50 values in the low nanomolar or subnanomolar range, as measured by the inhibition of [3H]zacopride binding. The SAR studies detailed herein delineated a number of structural features required for improving affinity. Some of the ligands were employed as 'molecular yardsticks' to probe the spatial dimensions of the lipophilic pockets L1, L2, and L3 in the 5-HT3 receptor cleft, while the 7-OH pyrroloquinoxaline analogue was designed to investigate hydrogen bonding with a putative receptor site H1 possibly interacting with the serotonin hydroxy group. The most active pyrroloquinoxaline derivatives showed subnanomolar affinity for the 5-HT3 receptor. In functional studies ([14C]guanidinium accumulation test in NG108-15 hybrid cells, in vitro) most of the tested compounds showed clear-cut 5-HT3 agonist properties, while some others were found to be partial agonists. Several heteroaromatic systems, bearing N-substituted piperazine moieties, have been explored with respect to 5-HT3 affinity, and novel structural leads for the development of potent and selective central 5-HT3 receptor agonists have been identified. Preliminary pharmacokinetic studies indicate that these compounds easily cross the blood brain barrier (BBB) after systemic administration with a brain/plasma ratio between 2 and 20, unless they bear a highly hydrophilic group on the piperazine ring. None of the tested compounds showed in vivo anxiolytic-like activity, but potential analgesic-like properties have been possibly disclosed for this new class of 5-HT3 receptor agonists.

Synthesis of new pyrrolo[l,2-a]quinoxalines: Potential non-peptide glucagon receptor antagonists

Synthesis of new pyrrolo[1,2-a]quinoxaline derivatives was achieved starting from various nitroanilines or orthophenyle-nediamines. Their affinity towards glucagon receptors was evaluated. Elsevier, Paris.