3027-01-8Relevant academic research and scientific papers
Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines
Neerathilingam, Nalladhambi,Bhargava Reddy, Mandapati,Anandhan, Ramasamy
, p. 15117 - 15127 (2021/10/25)
A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.
N-Heterocyclic Carbene/Cobalt Cooperative Catalysis for the Chemo- and Regioselective C?N Bond Formation between Aldehyde and Amines/Amides
Siddiqui, Asher M.,Khalid, Anam,Khan, Arif,Azad, Chandra S.,Samim, Mohd.,Khan, Imran A.
, p. 4281 - 4287 (2020/07/24)
A novel methodology for the construction of various secondary (4 examples), tertiary amides (31 examples), and imides (16 examples) by a Cobalt(II) catalyzed oxidative amide coupling in aqueous media. The Co(III)-TMC was reacted with N-Heteroatom Carbene to form active catalyst Co(II)NHC-TMC in situ which involves in the coordination with Breslow's intermediate and SET for the activation of aldehyde and amides. The mechanism for activation of amide and amine differs on the basis of SET based nucleophilic addition and ligand exchange respectively. The regeneration of the catalyst was achieved using Fe(III)(EDTA)-H2O2 as oxidant. The use of Co(II)TMC-O2 was also found equally efficient in the process. The method is found regioselective for N?H activation in the presence of equally susceptible ortho-C?H bond activation. And amines were found more susceptible then the corresponding amide for the reaction.
Ring-chain interconversion in high-performance polymer systems. 3. Cyclodepolymerization of poly(m-phenylene isophthalamide) (nomex) and entropically driven ring-opening polymerization of the macrocyclic oligomers so produced
Ben-Haida, Abderrazak,Hodge, Philip,Colquhoun, Howard M.
, p. 722 - 729 (2007/10/03)
A homologous series of macrocyclic oligoamides has been prepared in high yield by reaction of isophthaloyl chloride with m-phenylenediamine under pseudo-high-dilution conditions. The products were characterized by infrared and 1H NMR spectrosco
2-chloro-N,N-dibenzoylaniline: A selective N-benzoylating reagent
Kondo, Kazuhiro,Murakami, Yasuoki
, p. 1217 - 1219 (2007/10/03)
Highly selective benzoylation of a less hindered amino group in the presence of a more hindered amino group with 2-chloro-N,N-dibenzoylaniline (2d), a convenient to use and stable reagent, is described.
Mechanisms for the Reactions of Nitrones with Aroyl Chlorides
Heine, Harold W.,Zibuck, Regina,VandenHeuvel, William J. A.
, p. 3691 - 3694 (2007/10/02)
Reaction of nitrones with equivalent quatities of aroyl chlorides in anhydrous dioxane containing triethylamine aields N,N-diacylamines.Treatment of nitrons with 18O-labeled benzoyl chloride under these conditions forms N,N-diacylamines with the 18O label distributed equally between the two acyl groups.Reaction of nitrones with equivalent or excess amounts of aroyl chlorides in anhydrous dioxane in the absence of triethylamine brings about isomerization of the nitrones to amides. α-Phenyl-N-(p-tolyl)nitrone treated with benzoyl chloride leads to an amide containing 50percent of the 18O label.Both reactions can be rationalized on the basis of the formation of aroyloxy(benzylidene)ammonium chlorides which undergo elimination of acid anions or acid to yield nitrillium ions.Addition of the acid anions or acids to the nitrillium ions affords the precursors to the N,N-diacylamines or isomerized amides, respectively.
The Isoimide-Imide Rearrangement
Brady, Kieran,Hegarty, Anthony F.
, p. 121 - 126 (2007/10/02)
When imidoyl chlorides (8) are solvolysed in the pH range 3-13 in aqueous dioxan in the presence of acetate or benzoate ions, the isoimides (10) are formed in situ.These isoimides undergo acid (pH 11.5) catalysed acyl transfer to the solvent, giving the amides (12).But at intermediate pH (6-11) rearrangement to the N-acyl form (11) ( the Mumm rearrangement) alone occurs.The specific rate of this O N acyl group migration is pH independent and shows a low solvent effect (m 0.175).Substituents attached to carbon or nitrogen have the same effect (ρ -0.84).When the migrating group R is varied a non-linear Hammet plot is observed, with ρ +0.60 for electron-withdrawing and +1.65 for electron-donating substituents.The changeover point is a function of the migrating terminus varying from R=Ph (when Y=H) to R=p-tolyl (when Y=p-NO2).Rate-determining O N acyl transfer is suggested in all cases, but this is preceded by an equilibrium which favours the Z form (10a) when R is electron donating.
