89290-93-7Relevant academic research and scientific papers
Application of primary halogenated hydrocarbons for the synthesis of 3-Aryl and 3-Alkyl indolizines
Liu, Yan,Hu, Huayou,Zhou, Junyu,Wang, Wenhui,He, Youliang,Wang, Chao
, p. 5016 - 5024 (2017/07/10)
Indolizine is an important heterocyclic compound with several interesting properties that make it suitable for numerous applications in many fields, such as biology, medicine and materials. However, the synthesis of 3-Alkyl indolizines from bulky primary halogenated alkanes has not yet been reported. Herein, a transition-metal-free synthetic route to 3-Aryl and 3-Alkyl indolizines from electron-deficient alkenes, pyridines and primary halogenated hydrocarbons has been reported for the first time using a tandem reaction. The key step of this method is the oxidative dehydrogenative aromatization of a tetrahydroindolizine intermediate with 2,2,6,6-Tetramethylpiperidine-N-oxyl (TEMPO) as the oxidant. The advantages of this protocol are its use of easily available and low-cost starting materials, the transition-metal-free conditions and its ready scalability.
Efficient and chemoselective reduction of pyridines to tetrahydropyridines and piperidines via rhodium-catalyzed transfer hydrogenation
Wu, Jianjun,Tang, Weijun,Pettman, Alan,Xiao, Jianliang
supporting information, p. 35 - 40 (2013/03/13)
Promoted by iodide anion the rhodium complex dimer, [Cp RhCl 2]2, catalyzes efficiently the transfer hydrogenation of various quaternary pyridinium salts under mild conditions, affording not only piperidines but also 1,2,3,6-tetrahydropyridines in a highly chemoselective fashion, depending on the substitution pattern at the pyridinium ring. The reduction is conducted in azeotropic formic acid/triethylamine (HCOOH-Et 3N) mixture at 40 °C, with catalyst loadings as low as 0.005mol% being feasible. Copyright
Electrochemical Reactions. Part 26. Radicals Derived by Reduction of N-Alkylpyridinium Salts and Homologous N,N'-Polymethylenebispyridinium Salts. Cleavage of the Carbon-Nitrogen Bond
Grimshaw, James,Moore, Shirley,Trocha-Grimshaw, Jadwiga
, p. 485 - 490 (2007/10/02)
The stability of the radical zwitterions derived by electron addition to N-alkyl-2,4,6-triphenyl- and 4-phenylpyridinium salts has been examined.Rapid carbon-nitrogen bond cleavage occurs for benzyl and allyl substituents only when the 2,6-diphenyl substituents are present.The N-propyl group is not lost.Homologous N,N'-polymethylenebis(2,4,6-triphenylpyridinium) salts show two reversible one electron waves, distinct for the ethylene derivative and merging as the carbon chain lengthens so that ΔEo reaches the theoretical value of (RT/F) ln 4.
