21397-41-1Relevant academic research and scientific papers
A general and efficient CuBr2-catalyzed N-arylation of secondary acyclic amides
Wang, Mangang,Yu, Hua,You, Xinwen,Wu, Jun,Shang, Zhicai
, p. 2356 - 2362,7 (2020/09/16)
A general and efficient Cu(II)-catalyzed cross-coupling method is reported for the preparation of acyclic tertiary amides. Generally moderate to excellent yields and functional group tolerance were obtained with secondary acyclic amides and aryl halides as substrates in toluene. A general and efficient Cu(II)-catalyzed cross-coupling method is reported for the preparation of acyclic tertiary amides. Generally moderate to excellent yields and functional group tolerance were obtained with secondary acyclic amides and aryl halides as substrates in toluene. Copyright
A simple copper-catalyzed synthesis of tertiary acyclic amides
Racine, Emilie,Monnier, Florian,Vors, Jean-Pierre,Taillefer, Marc
supporting information; experimental part, p. 2818 - 2821 (2011/07/09)
The N-arylation of aromatic and aliphatic secondary acyclic amides, known to be poor nucleophiles, has been accomplished using a simple and cheap copper catalytic system. The corresponding tertiary acyclic amides, which can be found in numerous biologically active compounds, have been obtained in good to excellent yields.
Evaluation of the Polar-inductive and Mesomeric Effects exerted by para-Substituted Phenyl Rings on Contiguous Functionalities
Barchiesi, Emma,Bradamante, Silvia,Pagani, Giorgio A.
, p. 1091 - 1096 (2007/10/02)
The para C-13 shifts of the phenyl ring in PhCH2Ar (I) is used as a monitor to evaluate, in terms of the previously defined ?IB constants, the polar-inductive effect exerted by some para-substituted aryl rings.Analogously, the para C-13 shift of the phenyl ring in PhNHAr (IV) is used as a monitor to evaluate, in terms of the previously defined ?C- constants, the blended polar-inductive and mesomeric effects exerted by such para-substituted aryl rings.The same para C-13 data offer access, through a biparametric (DSP) treatment, to ?R- constants, which account for the mesomeric effects exerted by the same substituents. C-13 Shift data are also reported for the 4'-substituted sodium aryl(phenyl)amides PhN-Ar (VII) which have been prepared in Me2SO by deprotonation of PhNHAr.The ?C- values just obtained account successfully for the para C-13 shifts of the phenyl ring of (VII), for the para C-13 shifts of the phenyl ring of phenylhydrazones of para-substituted benzaldehydes, and for the acidity of aryl(phenyl)amines measured in Me2SO-H2O by Dolman and Stewart.The success of the biparametric treatment is limited by the small range of the ?IB values of the para-substituted aryl derivatives and by the scarcity of data.The ?IB set is linearly related to the set of ?I constants obtained from substituted acetic acids.Both the ?IB and the ?C- sets account successfully for the acidity of para-substituted benzoic acids in H2O, in Me2SO, and in the gas phase: a rationale is given.
REARRANGEMENT OF NITRONES TO AMIDES USING CHLOROSULFONYL ISOCYANATE
Joseph, Sajan P.,Dhar, D. N.
, p. 5979 - 5983 (2007/10/02)
Reaction of chlorosulfonyl isocyanate (CSI) with nitrones 1a-n and 5a,b has been studied. α,α,N-Triaryl nitrones 1a-n react with CSI to form the N,N-diaryl arylamides 3a-n and 4i-n in good yields.In the case of α-H,α,N-diaryl nitrones 5a,b however, two compounds viz., the rearranged product 11a,b and the 1,4-dihydro tetrazines 10a,b are formed.The effect of substituents on the rearrangement has been studied.It is found that the nature of the substituents has got a profound effect on the rearrangement.We have also noted that the rearrangement is independent of the syn or anti configurations of the nitrones.
