N-Carbamimidoyl-2,2,2-Trifluoro-N′-Arylacetimidamides as Important Intermediates for the Synthesis of 3-Amino-4-Aryl-5-(Trifluoromethyl)-1H-1,2,4-Triazoles

IF 2 3区 化学 Q2 CHEMISTRY, ORGANIC Journal of Heterocyclic Chemistry Pub Date : 2024-11-25 DOI:10.1002/jhet.4934
Salimeh Abdinasab, Ali Darehkordi, Alireza Abbasi
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Abstract

A novel series of N-carbamimidoyl-2,2,2-trifluoro-N′-arylacetimidamides (3a–j) have been prepared via condensation of 2,2,2-trifuoroacetimidoyl chlorides with guanidine in the presence Na and in dry EtOH solvent at ambient temperature. Then, these key intermediates were applied for the synthesized of 3-amino-4-aryl-5-(trifluoromethyl)-1H-1,2,4-triazoles (4a–j) under oxidative cyclization reaction in the presence of KI/I2 as an oxidant system and DMSO solvent. The target compounds were produced in high yields and without the need for isolation.

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n -氨基甲酰-2,2,2-三氟- n ' -芳基乙酰胺作为合成3-氨基-4-芳基-5-(三氟甲基)- 1h -1,2,4-三唑的重要中间体
以2,2,2-三氟乙酰氨基甲酰氯为原料,在Na存在下,在干燥的乙醚溶剂中,在常温下与胍缩合,制备了一系列新的n -氨基氨基甲酰-2,2,2-三氟- n′-芳基乙酰氨基甲酰(3a-j)。然后,将这些关键中间体应用于KI/I2作为氧化剂体系和DMSO溶剂存在下的氧化环化反应合成了3-氨基-4-芳基-5-(三氟甲基)- 1h -1,2,4-三唑(4a-j)。目标化合物产率高,无需分离。
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来源期刊
Journal of Heterocyclic Chemistry
Journal of Heterocyclic Chemistry 化学-有机化学
CiteScore
5.20
自引率
4.20%
发文量
177
审稿时长
3.9 months
期刊介绍: The Journal of Heterocyclic Chemistry is interested in publishing research on all aspects of heterocyclic chemistry, especially development and application of efficient synthetic methodologies and strategies for the synthesis of various heterocyclic compounds. In addition, Journal of Heterocyclic Chemistry promotes research in other areas that contribute to heterocyclic synthesis/application, such as synthesis design, reaction techniques, flow chemistry and continuous processing, multiphase catalysis, green chemistry, catalyst immobilization and recycling.
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