36160-02-8Relevant academic research and scientific papers
N-heterocyclic carbene catalyzed enantioselective [3 + 2] dearomatizing annulation of saturated carboxylic esters with n-iminoisoquinolinium ylides
Zhang, Pengfei,Zhou, Yu,Han, Xu,Xu, Jinyi,Liu, Hong
, p. 3879 - 3888 (2018/04/14)
The dearomatizing annulation reaction is a significant challenge in organic chemistry. The direct activation of α-carbons of simple saturated esters, as nucleophiles, is an important synthesis strategy. In the present study, we disclose [3 + 2] dearomatizing annulation reactions with direct activating α-carbons of saturated carboxylic esters and N-iminoisoquinolinium ylides, which possess highly enantioselective characteristics, catalyzed by N-heterocyclic carbenes (NHCs). The protocol achieves isoquinoline dearomatization and the construction of tricyclic chiral products under mild conditions with good yield, substrate tolerance, and diastereoselectivity as well as excellent enantioselectivity.
Ruthenium(II)-porphyrin catalyzed selective N-imidation of aromatic nitrogen heterocycles
Jiang, Yan,Zhou, Guo-Chuan,He, Guang-Li,He, Ling,Li, Ju-An,Zheng, Shi-Long
, p. 1459 - 1464 (2008/02/05)
Ruthenium(II)-porphyrin (0.5 mol%) catalyzed N-imidations of aromatic nitrogen heterocycles with phenyl(tosylimino)iodinane under mild conditions were achieved in good yields (94%). The effects of substituent, catalyst, temperature, and solvent on the re
Copper-catalyzed imination of pyridines using PhI=NTs as nitrene precursor
Jain, Suman L.,Sharma, Vishal B.,Sain, Bir
, p. 4385 - 4387 (2007/10/03)
The reaction of PhI=NTs with pyridines in the presence of a catalytic amount of Cu(II) triflate afforded the corresponding p-tolylsulfonyliminopyridinium ylides in excellent yields.
Cycloaddition Reactions of N-p-Toluenesulfonylimino Derivatives of Quinoline and Isoquinoline. A Route to Pyrazoloquinolines and Pyrazoloisoquinolines
Sundberg, Richard J.,Ellis, James E.
, p. 573 - 576 (2007/10/02)
N-p-Toluenesulfonylimino ylides of quinoline and isoquinoline give cycloadducts with electrophilic acetylenes at 105 deg C.The adducts are spontaneously aromatized under the conditions of their formation by elimination of p-toluenesulfinic acid to give py
The Reactions of 2-Alkynylbenzaldehydes with Hydrazides: a Route to Isoquinoline N-Imines
Anderson, Patrick N.,Sharp, John T.
, p. 1331 - 1334 (2007/10/02)
Sulphonyl- and acyl-hydrazones of 2-ethynylbenzaldehyde cyclise in the presence of base to give isoquinoline N-imines in moderate yield.The suggested mechanism involves primapy formation of the hydrazone anion followed by nucleophilic attack on the alkyne bond, either by anionic nitrogen to give an unstable 3H-2,3-benzodiazepine which rearranges to the isoquinoline N-imine, or by the neutral imine nitrogen to give the isoquinoline system directly.Attempts to extend the reaction to the semicarbazone and 2,4-dinitrophenylhydrazone were not successful.
