42792-95-0Relevant academic research and scientific papers
Iodination/Amidation of the N-Alkyl (Iso)quinolinium Salts
Tang, Juan,Chen, Xue,Zhao, Chao-Qun,Li, Wen-Jing,Li, Shun,Zheng, Xue-Li,Yuan, Mao-Lin,Fu, Hai-Yan,Li, Rui-Xiang,Chen, Hua
supporting information, p. 716 - 730 (2020/12/22)
The NaIO4-mediated sequential iodination/amidation reaction of N-alkyl quinolinium iodide salts has been first developed. This cascade process provides an efficient way to rapidly synthesize 3-iodo-N-alkyl quinolinones with high regioselectivity and good functional group tolerance. This protocol was also amenable to the isoquinolinium salts, thus providing a complementary method for preparing the 4-iodo-N-alkyl isoquinolinones.
Carbene-catalyzed aerobic oxidation of isoquinolinium salts: Efficient synthesis of isoquinolinones
Wang, Guanjie,Hu, Wanyao,Hu, Zhouli,Zhang, Yuxia,Yao, Wei,Li, Lin,Fu, Zhenqian,Huang, Wei
supporting information, p. 3302 - 3307 (2018/07/29)
A mild and environmentally friendly carbene-catalyzed aerobic oxidation of isoquinolinium salts was successfully realized. Accordingly, a diverse set of isoquinolinones and phenanthridinones was efficiently prepared in good to excellent yields. The mechanistic study indicates that the formation of an aza-Breslow intermediate is the crucial step in this transformation. This reaction features ambient air as the sole oxidant and oxygen source, a broad substrate scope, and excellent functional-group tolerance and proceeds under mild reaction conditions. Furthermore, a highly efficient synthesis of bioactive molecules and natural products including N-methylcrinasiadine, N-isopentylcrinasiadine, N-phenethylcrinasiadine, isoindolo[2,1-b]isoquinolin-5(7H)-one, PJ-34, rac-Gusanlung D, rosettacin, 8-oxopseudopalmatine and ilicifoline B was accomplished.
Reactions of isoquinolinium salts with hydroxylamine derivatives, 2nd communication N-(alkyl) and N-(aryl) substituted compounds
Moehrle,Niessen
, p. 532 - 540 (2007/10/03)
The N-alkyl- and N-aryl-isoquinolinium salts 7, 15-17 reacted with free hydroxylamine in pyridine to give the isoquinoline-2-oxide (9) as final product. The intermediate dioximes 8 were isolated and characterized by derivatisation with acetic anhydride to the oxime ester nitrile 10. From the reaction of 8 with trifluoroacetic anhydride/triethylamine 3-amino-isoquinoline-2-oxide (12) resulted after hydrolysis. Due to the electronic influence the 5-nitroisoquinolinium salts 1-3 react faster than the 5-hydroxy derivative 20, but with the same course of conversion via dioximes to amine oxides. An optimized method for preparation of the amine oxides was developed.
KINETICS OF HYDRIDE TRANSFER BETWEEN NITROGEN HETEROAROMATIC CATIONS
Bunting, John W.,Luscher, Mark A.
, p. 2524 - 2531 (2007/10/02)
The kinetics of the reduction of the 3-cyano-1-methylquinolinium, 4-cyano-2-methylisoquinolinium, and 2-methyl-5-nitroisoquinolinium cations by 9,10-dihydro-10-methylacridine, and also the reduction of these same three cations as well as the 10-methylacridinium cation by 5,6-dihydro-5-methylphenanthridine, have been investigated in 20percent acetonitrile - 80percent water, ionic strength 1.0, 25 deg C.The reactions of the 2-methyl-5-nitroisoquinolinium cation with both reductants, and also of the 4-cyano-2-methylisoquinolinium cation with 9,10-dihydro-10-methylacridine, display kinetic saturation effects in the pseudo-first-order rate constants as a function of heterocyclic cation concentration.These effects are consistent with the formation of 1:1 association complexes between hydride donor and acceptor prior to the rate-determining step of the reduction.The second-order rate constants for these reactions, and also those for analogous heterocyclic cation reductions by 1,4-dihydronicotinamides, show systematic variations as a function of the hydride donor and acceptor species.
A RATE AND EQUILIBRIUM STUDY OF THE ADDITION OF ACETONE ENOLATE ION TO THE 2-METHYL-5-NITROISOQUINOLINIUM CATION IN AQUEOUS SOLUTION
Bunting, John W.,Tam, James W.
, p. 973 - 979 (2007/10/02)
Rate and equilibrium constants for the reaction between acetone and the 2-methyl-5-nitroisoquinolinium cation to give 1-acetonyl-1,2-dihydro-2-methyl-5-nitroisoquinoline (2) have been evaluated over the pH range 10.0-11.3 in aqueous solutions at 25 deg C.This reaction is shown to occur under much milder conditions (temperature, pH) and in much shorter reaction times than previously used for the synthesis of this adduct.Analogous data for the reaction of hexadeuteroacetone with this heterocyclic cation are also presented.The formation of 2 is shown to be first order in each of acetone, isoquinolinium cation, and hydroxide ion, and is not catalyzed by carbonate buffer species.These data are consistent with the rate-determining attack of the acetone enolate anion upon the isoquinolinium cation.The microscopic reverse of this reaction is the uncatalyzed decomposition of 2, which is consistent with the observed pH independence of the first-order rate constant for this process.Quantitative comparisons of rates and equilibria for the addition of hydroxide ion and acetone enolate ion to this isoquinolinium cation and to substituted benzaldehydes are now available.
