Synthesis of novel 3-pyridinecarbonitriles with amino acid function and their fluorescence properties

Abstract

A variety of N-[(4,6-diaryl-3-pyridinecarbonitrile)-2-yl] amino acid esters 2-4 were synthesized through the reaction of 2-bromo-3-pyridinecarbonitriles 1 with the appropriate alpha-amino acid ester hydrochloride in refluxing dioxane in the presence of triethylamine as dehydrohalogenating agent. Similarly, N'-glycylglycine analogues 5 were obtained through the reaction of 1 with the dipeptide ester. On the other hand, attempts were made towards the construction of amino acid derivatives 7 through the reaction of 1 with aqueous solution alpha-amino acids 6 in refluxing pyridine, but were unsuccessful, and instead the unexpected 2-amino-3-pyridinecarbonitriles 8 were isolated. The fluorescence properties of the newly synthesized pyridines 2-5 were evaluated. Some of the prepared compounds show considerable antibacterial activity.

Experimental and theoretical studies of the nanostructured {Fe3O4@SiO2@(CH2)3Im}C(CN)3catalyst for 2-amino-3-cyanopyridine preparationviaan anomeric based oxidation

“…Hence, in consequence of the aforementioned biological significances of these versatile structural motifs, a number of procedures have been reported on this topic like microwave or ultrasound irradiation [10][11][12][13], hexadecyldimethyl benzyl ammonium bromide and triethylamine [14], DMF [15], acetic acid [16], Fe 3 O 4 [17], Cellulose-SO 3 H [18]and using earth Lewis acid catalyst [19]. Although, several catalyst and protocol have been studied for the preparation of the 2-amino-3-cyanopyridine derivatives, the methods suffer from one or more imperfection such as toxic solvent like benzene [20], multi-steps reaction pathway [21], high temperature and microwave assistance [22,23], prolonged reaction times and harsh reaction conditions with low yields. In the light of these facts, surveying a straightforward and newer recyclable catalytic environmentally congruous approach for the synthesis of these compounds is still a great day required and an interesting mission to the methodologists and would be valuable.…”

"Polyethylene Glycol-400 Used as Phase Transfer Catalyst for One-Pot Synthesis of 2-Amino-3- Cyanopyridine Derivatives Under Aqueous Conditions"

“…The reaction was established by synthesis of various 2-Amino-3-cyano pyridine derivatives using simple starting materials. In general, all the obtained products were clean and structures were confirmed by 1 H NMR, 13 C NMR, IR and Mass Spectral Analysis. …”

“…2-amino-3-cyano pyridine derivatives have attracted considerable interest as bioactive agents, 7,8 such as A2A Adenosine receptor antagonists, 9 IKK-β inhibitors, 10 a potent inhibitors of HIV-1 integrase, 11 modulate androgen receptor function 12 and anticancer agents. 13 The focal point of research in organic chemistry is to investigate newer recyclable solvents, catalysts and environmentally friendly approaches. Various eco-hardships can be satisfied by using green catalyst and green solvents.…”

2-(4-Methylpiperazin-1-yl)-4-phenyl-6-(thiophen-2-yl)-pyridine-3-carbonitrile

“…2-Alkoxypyridine-3-carbonitrile derivatives were reported to be active antimicrobial agents against Gram-positive, Gram-negative and acid fast bacteria and yeast [10]. Also, pyridine-3carbonitriles with amino acid functions were reported to exhibit considerable antimicrobial properties [11]. 2-Amino-3-cyanopyridine derivatives were proved to have antitubercular activity against Mycobaterium tuberculosis H 37 RV ATCC 27294, in BACTEC 12 B medium using the ALAMAR OPEN ACCESS M794 (Page 2) radiometric system comparing with the standard drug rifampin [12].…”