77930-24-6Relevant academic research and scientific papers
Copper-catalyzed synthesis of 1,2-disubstituted benzimidazoles from imidoyl chlorides
Yu, Hui,Zhang, Mei Shu,Cui, Li Ren
experimental part, p. 573 - 575 (2012/07/14)
A strategy for the synthesis of 1,2-disubstituted benzimidazoles has been developed and a variety of 1,2-disubstituted benzimidazoles were obtained from imidoyl chlorides and o-haloanilines via copper(I)-catalyzed reaction in moderate yields.
N -alkynyl imides (ynimides): Synthesis and use as a variant of highly labile ethynamine
Sueda, Takuya,Oshima, Ayumi,Teno, Naoki
supporting information; experimental part, p. 3996 - 3999 (2011/10/01)
This study describes the first reliable synthesis of N-alkynyl imides (ynimides). This was accomplished with a copper-catalyzed coupling reaction between alkynyl(triaryl)bismuthonium salts and five-membered imides. We also found that it was possible to utilize N-ethynyl phthalimide as a variant of the highly labile ethynamine. 4-Amino-1,2,3-triazole was successfully obtained via the CuAAC reaction of N-ethynyl phthalimide with azide followed by hydrazinolysis of the phthaloyl protecting group.
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.
