Guanidine derived ionic liquids: catalyst free medium for N-formylation of amines

Abstract

A remarkable improvement of both the chemical yield and the reaction condition, of Nformylation of amines with formic acid was found, when tetra-substituted guanidinium salts were added as ionic liquids. Effects of amount and the type of guanidinium salts on the outcome of the reaction were investigated. This procedure works well for sterically hindered primary amine as well as electron-deficient primary arylamines, primary and secondary amino alcohols, α-amino acid esters, hydroxylamines and N,N-dimethylhydrazine. The recovered ionic liquid can be recycled for four runs without loss of activity

Sulfonic Acid Functionalized Ionic Liquid in Combinatorial Approach, a Recyclable and Water Tolerant-Acidic Catalyst for One-Pot Friedlander Quinoline Synthesis

“…These ILs are miscible in water, and their homogeneous system is readily separated from the reaction product, combining advantages of both homogeneous and heterogeneous catalysis. In continuation of our interest in ionic liquid mediated chemical and biochemical transformations, we herein report the one pot domino approach for the synthesis of quinoline derivatives in Friedlander manner using TSIL as a catalyst (Scheme ). In this reaction, the catalyst plays a dual role; it ensures an effective condensation and cyclization of 2-aminoaryl ketone with second carbonyl group and it also promotes the aromatization to the final product.…”

Au NPs fabricated on biguanidine-modified Zr-UiO-66 MOFs: a competent reusable heterogeneous nanocatalyst in the green synthesis of propargylamines

“…In continuation of our previous studies in the field of nanocatalysts in organic synthesis, 33 after the successful synthesis of the UiO-66-bigua/Au(0) material using a post-synthetic modification method, we focused on its structural and physicochemical characteristics using different analytical techniques like FT-IR spectroscopy, SEM, TEM, EDX spectroscopy, elemental mapping and XRD. Fig.…”

“…The vibrations observed at 1259 cm −1 and 1665 cm −1 are assigned to the –NH 2 scissoring and C–NH 2 stretching of aromatic amines, respectively. 33 The broad band in the region of 3400–3500 cm −1 results from the symmetric and asymmetric stretching vibrations of free amines. 34,35 In Fig.…”

Highly efficient N-formylation of amines with ammonium formate catalyzed by nano-Fe3O4in PEG-400

“…Also, formamides are valuable intermediates for the synthesis of pharmaceutically active compounds such as substituted aryl imidazoles, 1 1,2-dihydroquinolines, 2 oxazolidinones 3 etc. 4,5 The formylation of amines is usually achieved by reacting amines with formic acid catalyzed by ZnO, 6 [TMG] + , 7 ZnCl 2 , 8 sulfated titania, 9 Amberlite IR-120, 10 indium metal, 11 iodine, 12 and sulfonic acid supported hydroxyapatite encapsulated g-Fe 2 O 3 . 13 Derivatives of formic acid like formate esters in the presence metal triates, 14 Bi(III) salts, 15 heteropoly acids, 16 Al(HSO 4 ) 3 , 17 silphos[PCl 3 -(SiO 2 ) n ], 18 or orthoformates 19,20 have also been used for the conversion of amines into formamides.…”