Novel Synthesis of Some New Fluorescent 2-Amino-3-cyanopyridines

Synthesis of Fluorescent 2,6‐Dicyano‐3,5‐Disubstituted Anilines Using Cellulose Sulfuric Acid in Aqueous Media

“…They suggested that under acidic conditions, contrary to basic media, the primary amines which could not act as a base, reacted as a reactant and appeared in the structure of the products. In agreement to their suggestion, we have recently reported the synthesis of some new fluorescent 2‐amino‐3‐cyanopyridines using pentane‐1,4‐dione, malononitrile, and amines in the presence of organic acids ( N ‐hydroxybenzamide or TsOH) . When Cellulose‐SA was used as the catalyst, the only products were 2,6‐dicyanoaniline derivatives instead of 2‐amino‐3‐cyano pyridines.…”

“…When Cellulose‐SA was used as the catalyst, the only products were 2,6‐dicyanoaniline derivatives instead of 2‐amino‐3‐cyano pyridines. We have already used some acidic catalysts in organic synthesis . In this report, we used 1,3‐diketones 1 and malononitrile in the aqueous media and presence of secondary amines (Me 2 NH, Et 2 NH, and piperidine) for the synthesis of some fluorescent 2,6‐dicyanoanilines 2 .…”

“…In contrast to our previous report, the amine did not act as the reactant; it played its interesting role twice, first, by producing enamine 4 as precursor of the more effective Michael acceptor 5 in the presence of Cellulose‐SA, and second, by deprotonation of intermediates 7 and 8 . Comparing our previous report on 2‐aminopyridines using the same reactants , in the present reaction, Cellulose‐SA prevents nucleophilic addition to the nitrile group and controls the reaction path.…”

“…It seems that designing a highly efficient environmentally benign procedure for the preparation of fluorescent‐substituted cyanobenzene derivatives is of great interest. Following our interest in the synthesis of fluorescent compounds , here we wish to report the synthesis of fluorescent 2,6‐dicyano‐3,5‐dialkyl anilines using environmentally benign cellulose sulfuric acid as the catalyst in aqueous media ( Scheme ).…”

3-Cyano-4,6-diphenyl-2-(phenethylamino)pyridine

“…Literature shows some reports on the synthesis of 2-amino-3-cyano-4,6-dialkylpyridines but there are few reports on diaryl ones [8][9][10][11]. Recently we have reported the synthesis of 2-amino-3-cyano-4,6-dialkyl pyridines by the one-pot multi-component reaction of 2,4-pentanedione, malononitrile and primary or secondary amines in the presence of Nhydroxy benzamide or p-toluenesulfonic acid as the acidic catalyst [12]. In continuation of our research on the synthesis of fluorescent compounds [12][13][14], we herein report the synthesis of 3-cyano-4,6-diphenyl-2-(phenethylamino) pyridine using N-hydroxybenzamide and ZnCl 2 as an organic acid and Lewis acid catalysts respectively (Scheme 1).…”