O-iodoxybenzoic acid in water: optimized green alternative for multicomponent one-pot synthesis of 2-amino-3,5-dicarbonitrile-6-thiopyridines

Abstract

Uma reação multicomponente do tipo one-pot de aldeído aromático, melanonitrilo e tiofenol na presença de ácido iodoxibenzóico (IBX) em meio aquoso forneceu 2-amino-3,5-dicarbonitrilo-6-tiopiridina em bons a excelentes rendimentos. Eventualmente, um catalisador poderia ser facilmente recuperado e reutilizado sem perda de sua propriedade catalítica.A multicomponent one-pot reaction of aromatic aldehyde, malononitrile and thiophenol in the presence of iodoxybenzoic acid (IBX) in aqueous media furnished 2-amino-3,5-dicarbonitrile-6-thiopyridine in good to excellent yield. Eventually, a catalyst could be easily recovered and reused without loss of its catalytic property.

Picolylamine–Ni(ii) complex attached on 1,3,5-triazine-immobilized silica-coated Fe3O4core/shell magnetic nanoparticles as an environmentally friendly and recyclable catalyst for the one-pot synthesis of substituted pyridine derivatives

“…37–39 Recently, the reaction between aldehyde, malononitrile, and thiol via a one-pot pseudo-four component reaction was evaluated as an efficient and simple method for the preparation of 2-amino-3,5-dicarbonitrile-6-thio-pyridines in the presence of a catalyst. In recent years, more effective catalysts for the preparation of pyridine derivatives have been reported, such as ZnCl 2 , 40 NAP-MgO, 41 iodoxybenzoic acid (IBX), 42 DBU, 43 KF/alumina, 44 scandium( iii ) triflate, 45 [bmIm]OH, 46 DABCO, 47 WEB, 48 Fe 2 O 3 @Fe 3 O 4 @Co 3 O 4 , 49 NaNH 2 , 50 Cu( i ) nanoparticles, 51 Zn( ii ) and Cd( ii ) MOFs, 52 microporous molecular sieves 4A, 53 and phosphotungstic acid/CTAB. 54 Nevertheless, some previously reported procedures remain valuable, albeit many of these procedures have significant drawbacks, such as low yields, tedious workup procedures, high temperatures, long reaction times, and the use of phosphine ligands and copper salts.…”

Non-Nucleoside Agonists of the Adenosine Receptors: An Overview

“…The increasingly eco-friendly requirements for synthetic protocols pushed several researchers to also look for new materials and conditions. Takale and co-workers [89] investigated the use of iodoxybenzoic acid (IBX) in aqueous media as an oxidant catalyst. The activity of IBX was compared with other compounds such as β-cyclodextrin, ceric ammonium nitrate or sulfate, tetrabutylammonium hydrogen sulphate, urea hydrogen peroxide, and cupreous chloride at reflux conditions for 3-5 h, but the yields of recovered product were 32-60%, while with IBX at 70 • C, for a 1.5 h reaction time, the yield was 80%.…”

A one-pot multicomponent K-10 clay catalyzed synthesis of 2-Amino-3,5-dicarbonitrile-6-thiopyridines

“…In addition, they are often used as anti-bacterial and anti-prion agents [10] (Figure 1). The multicomponent condensation of aldehyde, malononitrile, and thiol has been accomplished by using various organocatalysts such as Et3N [11], diethylamine [12], deep eutectic solvent (DES) [13], Baker's yeast [14], water extract of banana [15], tetra-n-butylammonium fluoride [16], o-Iodoxybenzoic acid [17], diethylamine [18], piperidine [19], imidazole [20], L-Arginine [21], N,N'-Di(1H-tetraazol-5-yl)-6H,12H-5,11ethanedibenzo[b,f][1,5]diazocine-3,9-dicarboxamide [22], choline methoxide [23] procuring target pyridines in 80-98% yields. Apart from organocatalysts, various nanomaterial-based catalysts have also been employed [24][25][26][27][28][29][30][31][32][33].…”