14251-91-3

Upstream product

• 4548-45-2 2-chloro-5-nitropyridine 
• 104-94-9 4-methoxy-aniline 
• 4487-59-6 2-bromo-5-nitropyridine 
• 2530-26-9 3-nitropyridine 

Relevant academic research and scientific papers

Kinetics and reactivity of substituted anilines with 2-chloro-5-nitropyridine in dimethyl sulfoxide and dimethyl formamide

The kinetics of the reaction of substituted anilines with 2-chloro-5-nitropyridine were studied in dimethyl sulfoxide (DMSO) and dimethyl formamide (DMF) at different amine concentrations and temperatures in the range 45-60°C. In both solvents the reaction was not a base-catalyzed one. A plot of ΔH# versus ΔS# for the reaction in DMSO and DMF gave good straight lines with isokinetic temperatures 128°C and 105°C, respectively. Good linear relationships were obtained from the plots of log k1 against σ° values at all temperatures with negative ρ values (- 1.63 to - 1.28 in DMSO) and (- 1.26 to -0.90 in DMF).

S NH Arylamination of 3-Nitropyridine: A Competitive Formation of 2-Arylamino-5-nitropyridines and 2-Arylamino-5-nitrosopyridines

Arylamination of 3-nitropyridine via the nucleophilic substitution of hydrogen leads to a mixture of 2-arylamino-5-nitropyridines and novel 2-arylamino-5-nitrosopyridines, with the latter as the major product. The proposed mechanism includes the formation of σ H -adducts and their further aromatization proceeding either through an oxidative pathway or intramolecular Red/Ox pathway of the S NH reaction. Moreover, we have shown that nitroso compounds can be selectively oxidized with m -chloroperbenzoic acid to give the corresponding nitro derivatives or their N -oxides, depending on the reaction temperature and the amount of oxidant.

Amination of heteroaryl chlorides: Palladium catalysis or SNAr in green solvents?

The reaction of heteroaryl chlorides in the pyrimidine, pyrazine and quinazoline series with amines in water in the presence of KF results in a facile SNAr reaction and N-arylation. The reaction is less satisfactory with pyridines unless an add

Design and synthesis of diarylamines and diarylethers as cytotoxic antitumor agents

Based on a shared structural core of diarylamine in several known anticancer drugs as well as a new cytotoxic hit 6-chloro-2-(4-cyanophenyl)amino- 3-nitropyridine (7), 30 diarylamines and diarylethers were designed, synthesized, and evaluated for cytotoxic activity against A549, KB, KB-vin, and DU145 human tumor cell lines (HTCL). Four new leads 11e, 12, 13a, and 13b were discovered with GI50 values ranging from 0.33 to 3.45 μM. Preliminary SAR results revealed that a diarylamine or diarylether could serve as an active structural core, meta-chloro and ortho-nitro groups on the A-ring (either pyridine or phenyl ring) were necessary and crucial for cytotoxic activity, and the para-substituents on the other phenyl ring (B-ring) were related to inhibitory selectivity for different tumor cells. In an investigation of potential biological targets of the new leads, high thoughput kinase screening discovered that new leads 11e, 12 and 13b especially inhibit Mer tyrosine kinase, a proto-oncogene associated with munerous tumor types, with IC50 values of 2.2-3.0 μM. Therefore, these findings provide a good starting point to optimize a new class of compounds as potential anticancer agents, particularly targeting Mer tyrosine kinase.

Solvent hydrogen bonding and structural effects on the reaction of 2-halo-5-nitropyridines with parasubstituted anilines in dimethylsulfoxide/ acetonitrile mixtures

Substitution reactions of some parasubstituted anilines with 2-chloro-5-nitropyridine and 2-bromo-5-nitropyridine were carried out conductometrically in dimethylsulfoxide/acetonitrile mixtures. The correlation of second order rate constants with Hammett's substituent constants yields a fairly linear straight line with a negative slope. The correlation of rate data with Kamlet-Taft's solvatochromic parameters is excellent (100R2= 97%) in both the substrates. The solvation model proposed is well supported by the solvatochromism exhibited by aniline in the solvent mixture under investigation. The molar extinction coefficient (εmax) of aniline varies appreciably up to ～25% with the change in composition of the mixture. The multivariate correlation analysis of εmax (with α, β, π) suggests that the solvation around NH2 moiety of aniline through hydrogen bond donor (HBD) property is found to be dominant in the solvation process and consequently in altering the rate. The observation is that the dominance of HBD property in solvation is further confirmed by the cyclic voltammetric oxidation of aniline in the solvent mixture.

Isothiocyanopyridine derivatives

New isothiocyanopyridines of the formula STR1 wherein R1 represents hydrogen, alkyl, substituted alkyl, cycloalkyl, Cycloalkenyl, or a group of the formula STR2 WHEREIN R3, R4 and R5 stand for hydrogen, alkyl, p