796-34-9Relevant academic research and scientific papers
Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis
Junor, Glen P.,Romero, Erik A.,Chen, Xi,Jazzar, Rodolphe,Bertrand, Guy
supporting information, p. 2875 - 2878 (2019/02/13)
Primary aminoboranes (RNHBR2), which are readily available by spontaneous dehydrocoupling of amines and boranes cleanly react at room temperature with aldehydes to give aldimines. The overall transformation from amines to aldimines can be conveniently performed by a sequential one-pot reaction. This synthetic strategy is especially useful for electron poor and bulky amines which are reluctant to react with aldehydes under dehydration conditions. Using a Glorius robustness screen, we show that this methodology is chemoselective, and functional group tolerant. Computational and experimental data support the irreversible formation of the aldimine product in marked contrast with traditional methods.
A Route to Polysubstituted Aziridines from Carbenes and Imines through a Nondiazo Approach
Luo, Hejiang,Chen, Kai,Jiang, Huanfeng,Zhu, Shifa
supporting information, p. 5208 - 5211 (2016/11/02)
An efficient method for the synthesis of polysubstituted aziridines utilizing enynones and imines is described. This transformation is achieved through the reaction of imines with donor/donor carbene intermediates, which were generated in situ from the cyclization of enynones. Furthermore, the resulted aziridines were good 1,3-dipoles, which could be efficiently trapped by dipolarophiles to give five-membered heterocycles. The obvious advantages of wide substrate scopes, mild reaction conditions, and high atom efficiency make this system highly appealing for construction of polysubstituted aziridines, 2,5-dihydropyroles, and 1,2,4-triazolidines.
Copper(I)-Catalyzed regioselective amination of N -aryl imines using TMSN3 and TBHP: A route to substituted benzimidazoles
Mahesh, Devulapally,Sadhu, Pradeep,Punniyamurthy, Tharmalingam
, p. 1644 - 1650 (2015/02/19)
A novel and efficient copper-catalyzed amination of N-aryl imines is described. This one-pot, multicomponent reaction, in which imine acts as a directing group by chelating to the metal center, affords a potential route for the transformation of the commercial aryl amines, aldehydes, and azides into valuable benzimidazole structural units with wide substrate scope and diversity. The synthetic and mechanistic aspects are presented.
Novel Synthesis of N,N-Diarylarylmethanamines from N-(Arylmethylene)arenamines and (Arylmethoxy)arenes
Paventi, Martino,Hay, Allan S.
, p. 5875 - 5882 (2007/10/02)
Various N,N-diarylarylmethanamines were synthesized by the reaction of N-(arylmethylene)arenamines with (arylmethoxy)arenes in dimethylformamide solution in the presence of a strong base as a catalyst which is obtained in situ by reacting metallic sodium with this solvent.In general, the reaction may be depicted as the reduction of the imine and addition, on the original imino nitrogen atom, of the aryl group (of the aryloxy moiety) of the ether and presumably oxidation of the arylmethoxy group of the ether to its corresponding aldehyde.Side reactions and a proposed reaction mechanism are discussed.
KINETICS AND MECHANISMS OF THE REACTION BETWEEN AROMATIC ALDEHYDES AND ANILINE IN ACETONITRILE
Maccarone, Emanuele,Mamo, Antonino,Perrini, Giancarlo
, p. 163 - 166 (2007/10/02)
Second-order rate constants and activation parameters for the reaction of some aromatic aldehydes (Ar=1-naphthyl; 2-naphthyl; 9-anthracenyl; 2-, 3-, or 4-pyridyl) with aniline in acetonitrile as solvent have been determined.The reactivities of the aldehyd
