3885-40-3

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 3-(TRIFLUOROMETHYL)QUINOXALINE-2-CARBOXYLATE is used as a trifluoromethylating reagent for the synthesis of pharmaceutical compounds. The trifluoromethyl group is a valuable moiety in medicinal chemistry, often enhancing the lipophilicity, metabolic stability, and bioavailability of drug candidates.
Used in Chemical Research:
In the field of chemical research, ETHYL 3-(TRIFLUOROMETHYL)QUINOXALINE-2-CARBOXYLATE serves as a versatile intermediate for the preparation of various quinoxaline-based derivatives. These derivatives can be further explored for their potential applications in material science, agrochemicals, and other specialty chemical areas.
Used in Fluorine Chemistry:
ETHYL 3-(TRIFLUOROMETHYL)QUINOXALINE-2-CARBOXYLATE is utilized in fluorine chemistry as a source of the trifluoromethyl anion, which can be used to alkylate a wide range of organic and inorganic substrates. This reagent contributes to the development of novel fluorinated molecules with unique properties and potential applications.

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 4544-43-8 Ethyl 2-Bromo-4,4,4-trifluoro-3-oxobutanoate 
• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 94609-23-1 ethyl 4,4,4-trifluoro-2-(hydroxyimino)-3-oxobutanoate 
• 79424-03-6 ethyl 4,4,4-trifluoro-2-butynate 
• 62-53-3 aniline 
• 1700-88-5 ethyl 4,4,4-trifluoro-3-(phenylamino)but-2-enoate 
• 49679-45-0 ethyl 3-chloroquinoxaline-2-carboxylate 

Downstream Products

• 1142190-60-0 3-(trifluoromethyl)quinoxaline-2-carboxylic acid 

Relevant academic research and scientific papers

Mechanistic Insight into Copper-Mediated Trifluoromethylation of Aryl Halides: The Role of CuI

The synthesis, characterization, and reactivity of key intermediates [Cu(CF3)(X)]-Q+ (X = CF3 or I, Q = PPh4) in copper-mediated trifluoromethylation of aryl halides were studied. Qualitative and quantitative studies showed [Cu(CF3)2]-Q+ and [Cu(CF3)(I)]-Q+ were not highly reactive. Instead, a much more reactive species, ligandless [CuCF3] or DMF-ligated species [(DMF)CuCF3], was generated in the presence of excess CuI. On the basis of these results, a general mechanistic map for CuI-promoted trifluoromethylation of aryl halides was proposed. Furthermore, on the basis of this mechanistic understanding, a HOAc-promoted protocol for trifluoromethylation of aryl halides with [Ph4P]+[Cu(CF3)2]- was developed.

Potassium Iodide-Promoted One-Pot Synthesis of Fluoroalkylated Quinoxalines via a Tandem Michael Addition/Azidation/Cycloamination Approach

Fluoroalkylated quinoxlines with various groups were efficiently synthesized via a one-pot tandem Michael addition/azidation/cycloamination process. Under the mild and metal-free conditions, a bis-imine intermediate (4a) was detected and isolated for the

Synthesis of new 2-substituted 3-(tri(di)fluoromethyl)-quinoxalines from 3-(trifluoromethyl)quinoxalin-2(1H)-oneand 3-(tri(di)fluoromethyl)quinoxaline-2-carboxylic acids

[Figure not available: see fulltext.] Starting from 3-(trifluoromethyl)quinoxalin-2(1H)-one, a wide range of new 2-substituted 3-(trifluoromethyl)quinoxalines were obtained, including amino, bromo, chloro, hydrazino, phenyl, α-furyl, formyl, methylsulfanyl, and methylsulfonyl derivatives. 3-(Tri(di)-fluoromethyl)quinoxaline-2-carboxylic acids were obtained for the first time and used for the synthesis of 2-amino-3-(tri(di)-fluoromethyl)quinoxalines and 2-(2-aminothiazol-4-yl)-3-(trifluoromethyl)quinoxaline.

Quinoxaline synthesis in novel tandem one-pot protocol

A variety of quinoxalines were synthesized via tandem one-pot procedure for the first time in water medium. The key strategy was the in situ preparation of α-halo-β-keto esters by the reaction of N-bromo succinimide with β-keto esters and further condensa

One-pot synthesis of quinoxaline-2-carboxylate derivatives using ionic liquid as reusable reaction media

The catalyst-free one-pot synthesis of quinoxaline-2-carboxylate is reported by the reaction of α-halo-β-ketoesters with 1,2-diamines using an ionic liquid as an environmentally benign solvent. The recovered ionic liquid was reused for four to five cycles

Reactions of Fluoroalkyl-Containing 2-Hydroxyimino-1,3-Dicarbonyl Compounds with o-Phenylenediamine

Fluoroalkyl-containing 2-hydroxyimino-3-oxo esters react with o-phenylenediamine in methanol (benzene, toluene) with formation of substituted quinoxalines. The same reaction in diethyl ether affords the corresponding 4-fluoroalkyl-4-hydroxy-3-hydroxyimino-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin- 2-ones. The reaction of 1,1,1-trifluoro-3-hydroxyimino-4-phenyl-2,4-butanedione in methanol results in cleavage of the latter and formation of 3-trifluoromethylquinoxalin-2-one; the same reactants in diethyl ether give rise to 2-hydroxy-3-hydroxyimino-4-phenyl-2-trifluoromethyl-2,3-dihydro-1H-1,5- benzodiazepine.