7465-93-2Relevant academic research and scientific papers
Efficient ligand-free copper-catalyzed N-arylation of amides with aryl halides in water
Yong, Fui-Fong,Teo, Yong-Chua,Chua, Guan-Leong,Lim, Gina Shiyun,Lin, Yizhen
supporting information; experimental part, p. 1169 - 1172 (2011/03/21)
A convenient and efficient protocol has been developed for the cross-coupling of amides and aryl iodides using a ligand-free copper(I) oxide catalyst in water. A variety of amide derivatives afforded the corresponding N-arylated products in moderate to good yields (up to 88%).
Synthesis, anticancer activity and docking of some substituted benzothiazoles as tyrosine kinase inhibitors
Bhuva, Hemal A.,Kini, Suvarna G.
experimental part, p. 32 - 37 (2011/10/09)
Protein tyrosine kinases occupy a central position in the control of cellular proliferation and its inactivation might lead to the discovery of a new generation anticancer compounds. Substituted benzothiazoles have been found to mimic the ATP-competitive
KINETICS AND MECHANISM OF THE AMINOLYSIS OF BENZOIC ANHYDRIDES
Lee, Byung Choon,Yoon, Ji Hyun,Lee, Cheal Gyu,Lee, Ikchoon
, p. 273 - 279 (2007/10/02)
Nucleophilic substitution reactions of benzoic anhydrides, in which one of the rings is substituted, with anilines were investigated in methanol.The product-formation step coincides with the rate-limiting step so that the two rate constants, kXY and kXZ, for the competitive reaction pathways can be dissected.The two cross-interaction constants, ρXY and ρXZ, especially an unusually large magnitude of the latter, indicate that the reaction proceeds by a frontside SN2 attack on either one of the carbonyl carbon with a strong interaction between the nucleophile (X) and the leaving group (Z).The mechanism is also supposed by the trends in the activation parameters.
EFFECT OF THE STRUCTURE ON THE RATE OF THE REACTIONS OF AROYL CHLORIDES WITH PRIMARY ARYLAMINES IN MIXTURES OF tert-BUTYL ALCOHOL AND CHLOROBENZENES. THE TRANSITION THROUGH ISOPARAMETRIC POINTS WITH RESPECT TO THE STRUCTURE PARAMETERS
Shpan'ko, I. V.,Likhomanenko, E. E.
, p. 1702 - 1710 (2007/10/02)
The rate of the reactions of aroyl chlorides with primary arylamines in 3.5, 5, and 7M solutions of tert-butyl alcohol in chlorobenzene at 25 deg C was measured.The effect of the structure of the reagents on the process rate was determined quantitatively by means of the Hammett-Taft and crossed correlation equations.The isoparametric points with respect to the structure of the substrate and the nucleophile were reached experimentally, and the transition through some of these points was also realised.It was found that the specific solvation of the primary arylamines by the tert-butyl alcohol was nonuniform in that an incre ase in the concentration of the alcohol in the investigated range reduced, did not change, and increased the rates of the reactions with 3-chloroaniline, 3-nitroaniline, and 3-nitro-5-methoxycarbonylaniline respectively.The effect of specific solvation on the behavior of the correlation parameters is discussed.
EFFECT OF STRUCTURAL FACTORS ON THE KINETICS OF FORMATION AND REACTIVITY OF THE INTERMEDIATE PRODUCT IN ACYL TRANSFER REACTIONS CATALYZED BY IMIDAZOLES
Dadali, V. A.,Zubareva, T. M.,Litvinenko, L. M.,Simanenko, Yu. S.
, p. 1543 - 1551 (2007/10/02)
During the stage-by-stage investigation of the aminolysis of benzoyl halides catalyzed by N-substituted imidazoles in low-polarity media the effects of the structure of the reagents and of the intermediate product on the rate constants for the forward and reverse reactions and on the equilibrium constant of the first reversible stage were studied.The rate (k2) of the reaction of the intermediate product with the arylamines at the second rate-determining stage was also investigated.Compared with the noncatalytic reaction the first stage of the catalytic reaction is characterized by the formation of an earlier transition state, similar to a tetrahedral intermediate product.The equilibrium constants for the formation of the intermediate product do not depend on the effect of the substituent in the benzoyl fragment (which is due to the identical sensitivity of the forward and reverse reactions to this effect) but varies in relation to the basicity of the imidazole and the character of solvation of the anion in the intermediate product.The transition state of the k2 reaction is reagent-like with a small degree of formation and cleavage of bonds.A theory is formulated in with the reactivity of the acyl-ammonium halides in low-polarity media is determined by two factors: a) The "dipositive" character of the C-N bond, due to its "destabilization;" b) the additional stabilization of the transition state through general-base assistance from the anion.
