1417697-01-8

Upstream product

• 4648-54-8 trimethylsilylazide 
• 221909-90-6 3-(2-aminophenyl)-1-(4-methoxyphenyl)prop-2-yn-1-one 
• 199454-06-3 (2-ethynylphenyl)carbamic acid 1,1-dimethylethyl ester 
• 100-07-2 4-methoxy-benzoyl chloride 
• 132725-52-1 (E)-3-(2-bromophenyl)-1-(4-methoxyphenyl)-prop-2-en-1-one 
• 6630-33-7 ortho-bromobenzaldehyde 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 1417697-00-7 2-(4-(4-methoxyphenyl)-1H-[1,2,3]triazolo[4,5-c]quinolin-1-yl)-1-phenylethanone 

Relevant academic research and scientific papers

Copper-Catalyzed Multicomponent Domino Reaction of 2-Bromobenzaldehydes, Aryl Methyl Ketones, and Sodium Azide: Access to 1 H-[1,2,3]Triazolo[4,5- c]quinoline Derivatives

A practical copper-catalyzed multicomponent reaction has been developed for the synthesis of 1H-[1,2,3]triazolo[4,5-c]quinoline derivatives from commercially available 2-bromobenzaldehydes, aryl methyl ketones, and sodium azide. This protocol integrated consecutive base-promoted condensation, [3 + 2] cycloaddition, copper-catalyzed SNAr, and denitrogenation cyclization sequences. Preliminary mechanistic studies revealed that CuBr2 acted as a multifunctional catalyst to streamline this domino process. The mild catalytic system enabled effective construction of one C-C and four C-N bonds in one operation.

TBAF-Catalyzed Tandem Synthesis of Triazolo[4,5-c]quinolines at Ambient Temperature

A mild, efficient and metal-free synthetic method for 1H-[1,2,3]triazolo[4,5-c]quinolines has been developed via intermolecular [3+2] cycloaddition of β-(2-aminoaryl)-α,β-ynones and TMS-N3, followed by intramolecular dehydration annulation sequential reactions. With 5 mmol-% of TBAF as catalyst, the reaction can smoothly proceed in DMF at ambient temperature to afford a wide range of functionalized 1H-[1,2,3]triazolo[4,5-c]quinolines in good to excellent yields.

Method for preparing 1H-[1,2,3]-triazolo[4,5-c]quinoline compounds

The invention discloses a method for preparing 1H-[1,2,4]triazole compounds. The method comprises the following steps: mixing beta-(2-aminoaryl)-alpha,beta-acetylenone (1), azidotrimethylsilane (2), afluorine-containing catalyst and a reaction solvent, reacting at 0-60 DEG C for 3-8 h, monitoring by TLC until the raw materials are completely converted, and carrying out post-treatment on the reacted solution to obtain the product (I). The cheap and easily available fluorine-containing reagent is used as a catalyst, the dosage of the catalyst is small, and no metal reagent is used, so post-treatment is simple, and the quality requirements of medicines and electronic materials are easily met; azidotrimethylsilane is used for replacing sodium azide to serve as an azido source, so toxicity issmall, safety is high, reaction conditions are mild, the reaction can be smoothly carried out at the room temperature, the substrate range is wide, and the yield is high.

One-pot synthesis of 4-substituted 1H-[1,2,3]triazolo[4,5-c]quinolines through CuO-promoted tandem cyclization reactions of (e)-3-(2-bromoaryl)-1- arylprop-2-en-1-ones with Sodium Azide

A facile and efficient protocol for the synthesis of 4-substituted-1H-[1,2, 3]triazolo[4,5-c]quinolines through a CuO-promoted tandem cyclization reaction has been developed. This method allows for the construction of two heterocyclic rings in a one-pot reaction of readily available (E)-3-(2-bromoaryl)-1-arylprop- 2-en-1-ones and sodium azide without the addition of any additive. A series of triazole-fused N-heterocyclic compounds could be prepared in moderate to good yields. Copyright