In water organic synthesis: Introducing itaconic acid as a recyclable acidic promoter for efficient and scalable synthesis of quinoxaline derivatives at room temperature

Abstract

Substituted quinoxaline derivatives are traditionally synthesized by co‐condensation of various starting materials. Herein, we describe a novel environmentally benign in water synthetic route for the synthesis of structurally and electronically diverse ninety quinoxalines with readily available substituted o‐phenylenediamine and 1,2‐diketones using cheap and biodegradable itaconic acid as a mild acid promotor in 1 hours. The reaction is performed at room temperature, which proceeds through cyclo‐condensation reaction followed by obtaining the aforesaid nitrogen‐containing heterocyclic adducts without performing the column chromatography up to 96% total yields. The simplicity, high efficiency, and reusable of the catalyst merits this reaction condition as “green synthesis” which enables it to be useful in synthetic transformations upto gram scale level.

Efficient Ru-Catalyzed Electrochemical Homo- and Heterocoupling Reaction of Terminal Alkynes: Synthesis, In Vitro Anticancer Activity, and Docking Study

“…Melting points were measured with a Buchi-540 micro melting point apparatus. Reactions were monitored using pre-coated silica gel 60 F 254 sheets (Merck) thin-layer chromatography (TLC) . For the MTT assay, cell lines were displayed and micrographed under an inverted microscope (Motic-AE30).…”

“…Reactions were monitored using pre-coated silica gel 60 F 254 sheets (Merck) thin-layer chromatography (TLC). 74 For the MTT assay, cell lines were displayed and micrographed under an inverted microscope (Motic-AE30). The absorbance was recorded on an enzyme-linked immunosorbent assay plate reader (FilterMax F3 Multi-Mode Microplate Readers, Molecular Devices).…”

Thiourea Dioxide Catalyzed Sustainable Synthesis of Diverse Quinoxaline and Pyrazine Derivatives in Aqueous Medium at Ambient Temperature

“…These include montmorillonite K-10, [17] o-iodoxybenzoic acid, [18] Itaconic acid, [19] polyaniline sulfate, [20] PTSA (p -Toluenesulfonic acid), [21] molecular iodine, [22,23] aqueous HF, [24] sulfamic acid, [25,26] acetic acid, [27,28] NH 4 Cl-CH 3 OH, [29] Amberlyst-15, [30] and metal catalysts such as silica-supported antimony(III) chloride, [31] cerium(IV) ammonium nitrate (CAN), [32] ZnO, [33] gallium(III) triflate, [34] zirconium(IV) chloride, [35] FeCl 3 , [36] sulfated polyborate [37] and SnCl 2 /SiO 2 . [38] A few methods for the synthesis of quinoxalines have also been reported by ultrasound irradiation [39,40] and microwave irradiation.…”