92961-15-4

Usage

Uses

Used in Organic Chemistry:
9-Phenyl-1,7-diazabicyclo[4.3.0]nona-2,4,6,8-tetraene is utilized as a building block for the synthesis of complex organic molecules. Its unique structure allows for the formation of various chemical entities through reactions with other compounds, contributing to the advancement of organic chemistry.
Used in Drug Development:
In the pharmaceutical industry, 9-phenyl-1,7-diazabicyclo[4.3.0]nona-2,4,6,8-tetraene is employed as a precursor for the development of new pharmaceutical compounds. Its reactivity and structural features make it a valuable component in the design and synthesis of innovative drugs, potentially leading to breakthroughs in medicinal chemistry.
Further research and testing are essential to fully explore and harness the capabilities of 9-phenyl-1,7-diazabicyclo[4.3.0]nona-2,4,6,8-tetraene across different applications, ensuring its potential is optimally utilized in both scientific and industrial settings.

InChI:InChI=1/C13H10N2/c1-2-6-11(7-3-1)12-10-14-13-8-4-5-9-15(12)13/h1-10H

Upstream product

• 504-29-0 2-aminopyridine 
• 70-11-1 α-bromoacetophenone 
• 307503-19-1 3-iodo-imidazo[1,2-a]pyridine 
• 98-80-6 phenylboronic acid 
• 274-76-0 imidazo[1,2-a]pyridine 
• 591-50-4 iodobenzene 
• 108-86-1 bromobenzene 
• 6200-60-8 imidazo[1,2-a]pyridine-3-carboxylic acid 
• 7436-90-0 2,2-dibromostyrene 
• 71-43-2 benzene 
• 122-78-1 phenylacetaldehyde 
• 108-90-7 chlorobenzene 
• 536-74-3 phenylacetylene 
• 59-88-1 phenylhydrazine hydrochloride 

Downstream Products

• 1609180-34-8 C₂₁H₁₈N₃O⁽¹⁺⁾*Cl^(1-) 

Relevant academic research and scientific papers

Cobalt-Catalyzed Direct Arylation of Imidazo[1,2-a]pyridine with Aryl Iodides

The Co(II)Cl2·6H2O catalyzed C–H activation/direct arylation of imidazo[1,2-a]pyridine with aryl/heteroaryl iodide is reported. The cost effective, ligand and additive free protocol using KOAc successfully afforded 3-arylimidazo[1,2-

Diversity-oriented synthesis toward aryl- And phosphoryl-functionalized imidazo[1,2-a]pyridines

We report herein an efficient synthesis of diversely polysubstituted imidazo[1,2-a]pyridines, a family of aza-heterocycles endowed with numerous biological properties, through a sequence involving two consecutive palladium-catalyzed cross-coupling reactions. First, we demonstrated that a Hirao coupling occurred straightforwardly in high yields at positions 3, 5, and 6 of imidazopyridine derivatives, giving access to a wide variety of substituted phosphonates, phosphinates, and phosphine oxides. In a second step, direct CH-arylation of phosphorylimidazopyridines with aryl halides was found to be effective and fully selective, leading to 3-aryl-substituted imidazopyridines in moderate to high yields depending on steric hindrance.

Facile synthesis of 3-substituted imidazo[1,2-: A] pyridines through formimidamide chemistry

A facile entry to 3-aryl/alkenyl/alkynyl substituted imidazo[1,2-a]pyridines (3a-p, 6a-d & 9a-9e) has been developed from readily available benzyl/allyl/propargyl halides and 2-amino pyridines as substrates via formimidamide chemistry that is devoid of caustic or expensive reagents, such as transition metal complexes. Quantum chemical calculations performed to understand the underlying mechanism of the transformation revealed a preference for intramolecular Mannich-type addition over pericyclic 1,5-electrocyclization for the systems reported herein that enable a Baldwin allowed 5-exo-trig cyclization instead of a formally anti-Baldwin 5-endo-trig process.

Iron(II)-Based Metalloradical Activation: Switch from Traditional Click Chemistry to Denitrogenative Annulation

A unique concept for the intermolecular denitrogenative annulation of 1,2,3,4-tetrazoles and alkynes was discovered by using a catalytic amount of Fe(TPP)Cl and Zn dust. The reaction precludes the traditional, more favored click reaction between an organic azide and alkynes, and instead proceeds by an unprecedented metalloradical activation. The method is anticipated to advance access to the construction of important basic nitrogen heterocycles, which will in turn enable discoveries of new drug candidates.

Virtual Screening Identifies Irreversible FMS-like Tyrosine Kinase 3 Inhibitors with Activity toward Resistance-Conferring Mutations

The use of covalent irreversible binding inhibitors is an established concept for drug development. Usually, the discovery of new irreversible kinase inhibitors occurs serendipitously, showing that efficient rational approaches for the rapid discovery of new drugs are needed. Herein, we report a virtual screening strategy that led to the discovery of irreversible inhibitors of FMS-like tyrosine kinase 3 (FLT3) involved in the pathogenesis of acute myeloid leukemia. A virtual screening library was designed to target the highly conserved Cys828 residue preceding the DFG motif by modification of reported reversible inhibitors with chemically reactive groups. Prospective covalent docking allowed the identification of two lead series, resulting in a massive increase in inhibition of kinase activity and cell viability by irreversible inhibitors compared to the corresponding reversible scaffolds. Lead compound 4b (BSc5371) displays superior cytotoxicity in FLT3-dependent cell lines to compounds in recent clinical trials and overcomes drug-resistant mutations.

Metal-free, base catalyzed oxidative amination and denitration reaction: Regioselective synthesis of 3-arylimidazo[1,2-a]pyridines

A metal-free, regioselective strategy for the synthesis of 3-arylimidazo[1,2-a]pyridines from β-nitrostyrenes and 2-aminopyridines using triethylamine as the catalyst and H2O2 (30% aq.) as the oxidant is reported. The use of an inexp

Metal-free C-H arylation of imidazoheterocycles with aryl hydrazines

A simple and efficient metal-free arylation of imidazo[1,2-a]pyridines at the C-3 position with arylhydrazine has been achieved at room temperature under ambient air conditions. Various 2,3-disubstituted imidazopyridines and imidazothiazoles were synthesized with high yields. The present methodology demonstrates the usefulness of commercially available aryl hydrazine as an arylating agent.

Metal- and base-free synthesis of imidazo[1,2-: A] pyridines through elemental sulfur-initiated oxidative annulation of 2-aminopyridines and aldehydes

The elemental sulfur-promoted oxidative cyclization reaction for the efficient synthesis of substituted imidazo[1,2-a]pyridines has been developed. Easily available 2-aminopyridines and aldehydes were directly assembled in a highly atom-economical fashion through oxidative annulation under metal- and base-free conditions. Besides arylacetaldehydes, aliphatic aldehydes were also compatible with this system to deliver the alkyl-substituted imidazo[1,2-a]pyridines in excellent yields with the capability of gram-scale synthesis.