Research on the reaction of furil with ammonium acetate

Abstract

KEYWORDSThe direct reaction of furil with ammonium acetate in refluxing glacial acetic acid under the absence of appropriate aldehydes was systematically studied. The principal product with furan rings and imidazole ring 2,4,5-tri(furan-2-yl)-1H-imidazole (I) was obtained in moderate yield, and two new byproducts containing furan rings were successfully purified by C18 reversed phase column. All compounds were characterized by elemental analysis, MS, IR, 1 H and 13 C NMR spectroscopy. The structure of I was further confirmed by the 13 C-1 H COSY spectroscopy. The putative reaction mechanism via stable 1,2-di(furan-2-yl)ethane-1,2-diimine, furan-2-yl-(2,4,5-tri-furan-2-yl-2H-imidazol-2-yl)-methanone and intermediate 5 traced by GC-MS was proposed.

Analytical method for lipoperoxidation relevant reactive aldehydes in human sera by high-performance liquid chromatography–fluorescence detection

“…Blank peaks were observed in all chromatograms, this might be attributed to the presence of short chain aliphatic aldehydes as impurities either in solvents or reagents, or incorporated from the air during the derivatization procedure [27]. Additionally, 2,2'-furil was reported to react with ammonium acetate in the presence of glacial acetic acid, in the absence of any aldehydes, producing trifurylimidazole fluorescent product [28]. Meanwhile, when injecting ACR following derivatization, two peaks were observed at t R of 8.0 and 24.8 min.…”

Microwave-assisted solvent-free synthesis and luminescence properties of 2-substituted-4,5-di(2-furyl)-1H-imidazoles

“…zole derivatives includes 1,2-diketone and appropriate aldehydes reflux in the presence of ammonium acetate and glacial acetic acid Parveen et al, 2007;Wang et al, 2011). In fact, these reactions commonly require higher temperature (over 118 • C) and the reaction time of 5-6 hours, whereas similar or higher yields and cleaner reaction profiles can be obtained using microwave heating for 10 minutes on solid support acidic alumina under solvent-free conditions (Table 2).…”

Synthesis of amine derivatives from furoin and furil over a Ru/Al2O3 catalyst

“…2,3,5,6-Tetra(furan-2-yl)pyrazine is generated as the main product at a temperature higher than 130 °C (Scheme 1), which is in accordance with an earlier report. 14 The yield is about 15–18% at full furoin conversion by reacting furoin at 140 °C for 4 h, using 0.06 g of furoin, 6 mL of DMF and 1 g of ammonium acetate (or 0.22 g NH 3 ). A myriad of minor products are generated with low yield (<5%), including 2-amino-1,2-di(furan-2-yl)ethan-1-ol.…”