87573-11-3Relevant articles and documents
Synthesis of 2-Formylpyrroles from Pyridinium Iodide Salts
Xu, Ke,Li, Wenjing,Sun, Rui,Luo, Lihua,Chen, Xue,Zhang, Chunchun,Zheng, Xueli,Yuan, Maolin,Fu, Haiyan,Li, Ruixiang,Chen, Hua
, p. 6107 - 6111 (2020)
The first I2-mediated synthesis of 2-formylpyrroles from pyridinium salts is reported. This protocol enables the synthesis of diversely substituted 2-formylpyrroles in good yields under operationally simple conditions. The detailed mechanistic studies reveal that the reaction proceeds via a novel H2O-triggered ring opening of the pyridinium salt and a subsequent intramolecularly nucleophilic addition sequence.
Regioselective Direct C-H Trifluoromethylation of Pyridine
Yang, Xiao,Sun, Rui,Li, Shun,Zheng, Xueli,Yuan, Maolin,Xu, Bin,Jiang, Weidong,Chen, Hua,Fu, Haiyan,Li, Ruixiang
supporting information, p. 7108 - 7112 (2020/10/02)
A highly efficient and regioselective direct C-H trifluoromethylation of pyridine based on an N-methylpyridine quaternary ammonium activation strategy has been developed. A variety of trifluoromethylpyridines can be obtained in good yield and excellent re
Stereodivergent Synthesis of Alkenylpyridines via Pd/Cu Catalyzed C-H Alkenylation of Pyridinium Salts with Alkynes
Chen, Hua,Haiyan, Fu,Jiang, Weidong,Li, Ruixiang,Li, Shun,Li, Wenjing,Tang, Juan,Xu, Bin,Yuan, Maolin,Zheng, Xueli
supporting information, p. 7814 - 7819 (2020/11/03)
The first Pd/Cu catalyzed selective C2-alkenylation of pyridines with internal alkynes has been developed via the pyridinium salt activation strategy. Importantly, the configuration of the product alkenylpyridines could be tuned by the choice of the proper N-alkyl group of the pyridinium salts, thus allowing for both the Z- and E-alkenylpyridines synthesized with good regio- and stereoselectivity. A plausible mechanism was proposed based on the Hammett study and KIE experiment.
C6-Selective Direct Arylation of 2-Phenylpyridine via an Activated N-methylpyridinium Salt: A Combined Experimental and Theoretical Study
Yin, Changzhen,Zhong, Kangbao,Li, Wenjing,Yang, Xiao,Sun, Rui,Zhang, Chunchun,Zheng, Xueli,Yuan, Maolin,Li, Ruixiang,Lan, Yu,Fu, Haiyan,Chen, Hua
supporting information, p. 3990 - 3998 (2018/09/12)
An elegant pre-activation strategy, based on the formation of N-methylpyridinium iodide salts for C6-selective direct arylation of 2-phenylpyridines using Pd/Cu cooperative catalysis, has been developed. By this methodology, a wide range of unsymmetrical 2, 6-diarylpyridines were synthesized with high reactivity and regioselectivity as well as good functional group tolerance. In particular, challenging substrates bearing electron donating groups (EDGs), such as OMe, NMe2, were also successfully employed in this reaction. Deuterium incorporation studies revealed that the C?H bond acidity is improved significantly in N-methylpyridinium salts compared with their N-Oxide and N-iminopyridinium ylide counterparts, thus solving the long-standing problem associated with previous strategies for the synthesis of diaryl pyridines. Finally, the control experiments and DFT calculations supported a Pd-catalyzed and Cu-mediated mechanism in which a carbenoid copper species that is formed in-situ from N-methylpyridinium salts, participates in a Pd-catalyzed arylation followed by an iodide-promoted N-demethylation process. (Figure presented.).
REACTIONS OF N-(4-METHOXYBENZYLIDENE)-N,N-DIALKYLIMINIUM AND 2-(4-METHOXYPHENYL)PYRIDINIUM SALTS WITH ALIPHATIC AMINES
Blokhin, A. V.,Tyurekhodzhaeva, M. A.,Bazhenov, D. V.,Bobrovskii, S. I.,Bundel', Yu. G.
, p. 1022 - 1025 (2007/10/02)
The reaction of 4-methoxybenzylideneiminium salts with methylamine and dimethylamine on heating results in replacement of the MeO group by an alkylamino-group, whereas the reaction with piperidine affords 3,5-bis-(4-methoxybenzyl)pyridine.N-Methyl-2-(4-me
Hydroxyphenyl-1-methylpyridinium-iodide as Potential Reactivators of Acetylcholinesterase Poisoned with Organophosphorus Compounds
Riggio, Gaetano,Hopff, Wolfgang Herbert,Hofmann, Alfred Andre,Waser, Peter Gaudenz
, p. 1039 - 1045 (2007/10/02)
It was our aim to reactivate acetylcholinesterase poisoned with sarin.We synthesized 2-(o-hydroxyphenyl)-1-methylpyridinium-iodide (9), 2-(p-hydroxyphenyl)-1-methylpyridinium-iodide (19) and 4-(o-hydroxyphenyl)-1-methylpyridinium-iodide (14) as potential reactivators.All substances showed moderate toxicity against mice; their reactivity potency in vitro and in vivo was negligible.
