Rad a 2-Amino-4,6-diphenylnicotinonitriles were prepared by using Fe3O4@SiO2@(CH2)3Im}C(CN)3 as a nanostructured catalyst with an ionic liquid tag under solvent free and benign conditions. Experimental evidences and theoretical studies confirmed that the final step of the synthetic pathway is proceeded via an anomeric based oxidation mechanism. A good range of aromatic aldehydes were condensed with acetophenone derivatives, malononitrile and ammonium acetate to afford their corresponding products in short reaction times and good to high yields.
The oxidative aromatization of 1,3,5-trisubstituted pyrazolines and 1,4-dihydropyridines using 1,2,4-triazolinediones as oxidizing agents was studied. It is confirmed that the “anomeric-based oxidation” passes through a concerted oxidation via hydrogen abstraction–addition.
Experimental and computational studies in the synthesis of 2-amino-4,6-diphenylnicotinonitrile using HBF 4 as an oxidizing promoter catalyst under mild and solvent free conditions were carried out. The suggested anomeric based oxidation (ABO) mechanism is supported by experimental and theoretical evidence. The theoretical study shows that the intermediate isomers with 5R-and 5S-chiral positions have suitable structures for the aromatization through an anomeric based oxidation in the final step of the mechanistic pathway.
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