129298-14-2

Upstream product

• 2213-63-0 2,3-dichloroquinoxaline 
• 100-46-9 benzylamine 

Downstream Products

• 1223415-78-8 1-benzyl-2-propyl-1H-pyrrolo[2,3-b]quinoxaline 
• 1223415-71-1 1-benzyl-2-phenyl-1H-pyrrolo[2,3-b]quinoxaline 
• 1223415-76-6 1-benzyl-2-butyl-1H-pyrrolo[2,3-b]quinoxaline 
• 1458658-69-9 N-allyl-N-benzyl-3-chloroquinoxaline-2-amine 
• 1234370-94-5 1-benzyl-1H-pyrrolo[2,3-b]quinoxaline-2-carbaldehyde 
• 1436860-23-9 N-benzyl-3-(morpholin-4-yl)quinoxalin-2-amine 
• 125103-17-5 2-Amino-1-benzyl-3-(4-methylthiazol-2-yl)pyrrolo<2,3-b>quinoxaline 

Relevant academic research and scientific papers

Synthesis of unexpected pyrrolo[2,3- b ]quinoxaline-2-carbaldehydes via sonogashira coupling reaction

The reaction of a number of N-alkyl-3-chloroquinoxaline-2-amines with propargyl bromide in the presence of PdClPPhand copper(I) iodide in wet morpholine leads to the formation of the unexpected N-substituted pyrrolo[2,3-b]quinoxaline-2-carbaldehydes in good yields. A possible mechanism for the conversion is suggested. Georg Thieme Verlag Stuttgart.

Ligand-free MCR for linking quinoxaline framework with a benzimidazole nucleus: A new strategy for the identification of novel hybrid molecules as potential inducers of apoptosis

We report a true MCR involving the reaction of N-(prop-2-ynyl)quinoxalin-2- amine derivatives with 2-iodoanilines and tosyl azide in the presence of 10 mol% of CuI and Et3N in DMSO to afford the pre-designed hybrid molecules containing quinoxaline framework linked with a benzimidazole nucleus. The MCR proceeds in the absence of any ligand and/or lateral addition of the catalyst/base affording products within 30 min in good yields, some of which showed encouraging apoptosis inducing properties in zebrafish. This journal is the Partner Organisations 2014.

Ligand/PTC-free intramolecular Heck reaction: Synthesis of pyrroloquinoxalines and their evaluation against PDE4/luciferase/oral cancer cell growth in vitro and zebrafish in vivo

A series of 1,3-disubstituted pyrrolo[2,3-b]quinoxalines has been designed for the potential inhibition of PDE4 without inhibiting luciferase. A ligand/PTC (phase transfer catalyst) free intramolecular Heck cyclization strategy was used to prepare these compounds, some of which showed significant inhibition of PDE4B (IC50 ≈ 5-14 μM) and growth inhibition of oral cancer cells (CAL 27) but not inhibition of luciferase in vitro. They also showed acceptable safety profiles but no apoptosis in zebrafish embryos.

AlCl3 induced C-N bond formation followed by Pd/C-Cu mediated coupling-cyclization strategy: Synthesis of pyrrolo[2,3-b]quinoxalines as anticancer agents

AlCl3 facilitated C-N bond forming reaction between 2,3-dichloroquinoxaline and anilines affording a convenient method for the preparation of N-aryl substituted 3-chloroquinoxalin-2-amines. A related N-benzyl derivative, however, was prepared via a conventional method. These N-alkyl/aryl substituted 3-chloroquinoxalin-2-amines on coupling with terminal alkynes in toluene under Pd/C-Cu catalysis afforded a range of 1,2-disubstituted pyrrolo[2,3-b]quinoxalines within 3-5 h in good to excellent yields. Some of the compounds synthesized showed promising anti-proliferative properties when tested in vitro against two cancer cell lines. Docking studies indicated that these molecules interact well with human Akt in silico.

One-pot synthesis of 1,2-disubstituted pyrrolo[2,3-b]quinoxalines via palladium-catalyzed heteroannulation in water

The reaction of N-alkyl-3-chloroquinoxaline-2-amines with 1-alkynes, catalyzed by Pd-Cu, in the presence of sodium lauryl sulfate as the surfactant in water, leads to the one-pot formation of 1,2-disubstituted pyrrolo[2,3-b]quinoxalines in good-to-high yields.

HETEROARYLATION OF ACETONITRILES. 3. HETREOARYLATION OF PYRIDIN-2-YL AND QUINOLIN-2-YLACETONITRILES BY CHLOROQUINOXALINES

It has been shown that α-chloroquinoxalines heteroarylate pyridin-2-yl and quinolin-2-ylacetonitriles primarily at the methylene group.A method has been developed for synthesizing 1-R-2-amino-3-heteroarylpyrroloquinoxalines permitting the preparation of compounds containing the pyridine and quinoline nuclei.