94129-62-1

Usage

InChI:InChI=1/C15H14N2/c1-2-16-15-11-7-3-5-9-13(11)17-14-10-6-4-8-12(14)15/h3-10H,2H2,1H3,(H,16,17)

Upstream product

• 73302-63-3 9-ethoxyacridine 
• 75-04-7 ethylamine 
• 110166-26-2 aminacrine 
• 75-03-6 ethyl iodide 
• 1207-69-8 9-Chloroacridine 
• 7788-69-4 1-phenyl-1H-indazole 
• 10407-11-1 2-Brom-benzaldehyd-phenylhydrazon 
• 271-44-3 benzimidazole 
• 591-50-4 iodobenzene 

Relevant academic research and scientific papers

Preparation method of 9-aminoacridine and derivatives thereof

The invention relates to a preparation method of 9-aminoacridine and derivatives thereof, and belongs to the technical field of organic synthesis. The preparation method of 9-aminoacridine and derivatives thereof comprises the following steps: adding a compound represented by a formula III into a polar aprotic solvent, then introducing a compound represented by a formula II, carrying out a reaction at a temperature of 70-120 DEG C, and after the reaction is finished, separating and purifying an obtained reaction solution to obtain 9-aminoacridine represented by a formula I and the derivativesthereof. The preparation method can be used for preparing the final product by a one-pot method, and is short in synthetic route, simple and convenient to operate, free of intermediates, high in yieldand low in cost. The method has the advantages of mild reaction conditions, low solvent corrosivity, low price, easy availability and recyclability, ensures the long-term operation of reaction equipment, enhances the operation safety factor, further lowers the production cost, and is suitable for large-scale production and application.

2-Ethyl-1-phenylindazolium hexafluorophosphate. N-heterocyclic carbene formation, rearrangement, ring-cleavage reactions, and rhodium complex formation

2-Ethyl-1-phenylindazolium hexafluorophosphate was deprotonated by potassium 2-methylbutan-2-olate to give the N-heterocyclic carbene of indazole, i.e., indazol-3-ylidene. This N-heterocyclic carbene undergoes a ring transformation to 9-ethylaminoacridine

Pericyclic rearrangements of N-heterocyclic carbenes of indazole to substituted 9-aminoacridines

On deprotonation, 1-arylindazolium salts form 1-arylindazol-3-ylidenes which rearrange spontaneously via ring cleavage, ring closure and subsequent proton transfer to substituted 9-aminoacridines. By contrast, the N-heterocyclic carbene of 2-phenylindazol