[TEATNM] and [TEATCM] as novel catalysts for the synthesis of pyridine-3,5-dicarbonitriles via anomeric-based oxidation

Abstract

The synthesis of 2-amino-4-aryl-6-(arylamino)pyridine-3,5-dicarbonitriles was carried out using [TEATNM] and [TEATCM] as catalysts via anomeric-based oxidation.

Multicomponent Reactions, Solvent-Free Synthesis of 2-Amino-4-aryl-6-substituted Pyridine-3,5-dicarbonitrile Derivatives, and Corrosion Inhibitors Evaluation

“…From the synthetic aspect, most of the existing studies on 2-amino-4-aryl-6-substituted pyridine-3,5-dicarbonitrile derivatives [22] were synthesized by ZnCl 2 -catalyzed multistep methods [23] and one-pot multicomponent reactions [24] with good yield. e addition of corrosion inhibitors is a useful approach to protect mild steel (MS) surfaces from corrosion damage [25].…”

1,10‐Phenanthroline‐Based Molten Salt as a Bifunctional Sulfonic Acid Catalyst: Application to the Synthesis of N‐Heterocycle Compounds via Anomeric Based Oxidation

“…Very recently we have introduced a new concept entitled “anomeric based oxidation (ABO) ” susceptible molecules and intermediates which can released H 2 in the presence of acidic catalysts . Based on this concept, driving force of aromatization to support losing H 2 molecule from intermediate ( III ) via anomeric based oxidation (ABO) and the desired product was obtained (Scheme ).…”

“…Very recently we have introduced a new concept entitled "anomeric based oxidation (ABO) " susceptible molecules and intermediates which can released H 2 in the presence of acidic catalysts. [51][52][53][54][55][56][57][58][59] Based on this concept, driving force of aromatization to support losing H 2 molecule from intermediate (III) via anomeric based oxidation (ABO) and the desired product was obtained (Scheme 4). In contrast to the reported aerobic oxidation mechanism for the final step of above said reaction, [22] we carried out the target reaction under argon atmosphere for approving anomeric based oxidation (ABO).…”

Synthesis of a novel and reusable biological urea based acidic nanomagnetic catalyst: Application for the synthesis of 2‐amino‐3‐cyano pyridines via cooperative vinylogous anomeric based oxidation

“…In these situations, anomeric effect leads to axial preference for acceptor groups at the anomeric positions (Scheme 1). [53] In this paper, in the following of our interest to expand new established term entitled anomeric based oxidation (ABO) [61][62][63][64][65][66][67][68][69] and also presenting new and efficient protocols for synthesis of biological valuable structures using nanomagnetic based catalysts, [70][71][72][73][74][75][76][77][78][79] we reported the rational design, synthesis, characterization and catalytic performance of a novel biological urea based nano magnetic catalyst namely Fe 3 O 4 @SiO 2 @(CH 2 ) 3 -urea-benzimidazole sulfonic acid in the synthesis of 2-amino-3-cyano pyridines via vinylogous anomeric based oxidation pathway (Scheme 5, 6). In triazaphenalene three anomeric interactions assisted the hydride removal and generated a stable guanidinium cation in acidic conditions (Scheme 2).…”

“…The obtained data show that compare to the C-N bond of the model compound SCHEME 1 Axial preference for acceptor group at the anomeric position SCHEME 2 Cooperative anomeric effect assisted the hydride removal from triazaphenalene SCHEME 3 Anomeic effect versus cooperative vinylogous anomeric effect SCHEME 4 Elongation of exocyclic C-N bond due to the existence of vinylogous anomeric effect SCHEME 5 General route towards the synthesis of Fe 3 O 4 @SiO 2 @(CH 2 ) 3 -urea-benzimidazole sulfonic acid SCHEME 6 Synthesis of 2-amino-3cyano pyridines using Fe 3 O 4 @SiO 2 @(CH 2 ) 3 -urea-benzimidazole sulfonic acid as catalyst FIGURE 1 FT-IR spectra of Fe 3 O 4 @SiO 2 @(CH 2 ) 3 -urea-benzimidazole sulfonic acid and corresponding intermediates without oxygen, the exocyclic C-N bond is 0.02-0.03 Å longer (Scheme 4). [53] In this paper, in the following of our interest to expand new established term entitled anomeric based oxidation (ABO) [61][62][63][64][65][66][67][68][69] and also presenting new and efficient protocols for synthesis of biological valuable structures using nanomagnetic based catalysts, [70][71][72][73][74][75][76][77][78][79] we reported the rational design, synthesis, characterization and catalytic performance of a novel biological urea based nano magnetic catalyst namely Fe 3 O 4 @SiO 2 @(CH 2 ) 3 -urea-benzimidazole sulfonic acid in the synthesis of 2-amino-3-cyano pyridines via vinylogous anomeric based oxidation pathway (Scheme 5, 6).…”