Intramolecular oxidative cyclization of N -(2,2,2-trifluoro-1-(phenylimino)ethyl)benzimidamide
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ORIGINAL ARTICLE
Intramolecular oxidative cyclization of N‑(2,2,2‑trifluoro‑1‑(phenylimino)ethyl)benzimidamide Elham Kazemi1 · Ali Darehkordi1 Received: 19 July 2019 / Accepted: 16 September 2019 © Springer Nature Switzerland AG 2019
Abstract A fast and convenient method for synthesis of 1,3-diaryl-5-(trifluoromethyl)-1H-1,2,4-triazole compounds has been described via intramolecular oxidative cyclization of the N-(2,2,2-trifluoro-1-(arylimino)ethyl)benzimidamide intermediates by I 2/KI in excellent yields without any purification. N-(2,2,2-Trifluoro-1-(arylimino)ethyl)benzimidamide intermediates which are used in this project have been synthesized from the reaction of N-aryl-2,2,2-trifluoroacetimidoyl chlorides and benzamide hydrochloride derivatives at room temperature for the first time. Graphic abstract
Keywords 2,2,2-Trifluoro acetimidoyl chloride · Amidine · Oxidative cyclization · 1,2,4-Triazoles
Introduction Amongst heterocyclic compounds, nitrogen heterocycles are very important [1]. 1,2,4-Triazoles as the most stable, nitrogen-rich heterocyclic compounds and also N-heterocycles, show high levels of biological activities such as antifungal, antibacterial, anticancer, antimicrobial, anticoagulant, Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11030-019-09995-8) contains supplementary material, which is available to authorized users. * Ali Darehkordi [email protected]; [email protected] 1
Department of Chemistry, Vali-e-Asr University, Rafsanjan 77176, Iran
anticonvulsant, and antidepressant [2–8]. For example, rizatriptan [9] as agent for acute treatment of migraine headaches and 3-(2-ethyl phenyl)-5-(3-methoxyphenyl)1H-1,2,4-triazole (DL111-IT) [10–12] as a non-hormonal antifertility agent are commercially available drugs (Fig. 1). Furthermore, 1,2,4-triazoles can be used as amide bond isostere for the design of receptor ligands that show antitumor and anticancer activity. Figure 1 shows some of the heterocyclic structures which have a 1,2,4-triazole core and are used in pharmaceutical applications [13]. There are various methods for synthesis of 1,2,4-triazoles [14–16]. For example, in 2003, Holla and et al. [17] reported synthesis of 1,2,4-triazole compounds in the presence of secondary amines and formaldehyde. Amidines, in addition to being used in the synthesis
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and lipophilicity of the molecule [28–31]. In recent years, reactions of trifluoromethylation have been extensively investigated, in order to synthesis new organofluorine compounds [32–34]. Also heterocyclic compounds bearing a 3-trifluoromethylphenyl substituent protect chlorophyll from photooxidative degradation during photosynthesis [35]. Because of above mentioned reasons and in continues of our research for the synthesis of heterocyclic compounds contain trifluoromethyl group with biological activity [32, 33], herein, we report an I2/KI-mediated oxidative N–N bond formation reaction to produce trifluoromethylphenyl-substitu
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