6324-18-1Relevant articles and documents
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.
High regiocontrol in the nucleophilic ring opening of 1-aralkyl-3,4- epoxypiperidines with amines - A short-step synthesis of 4- fluorobenzyltrozamicol and novel anilidopiperidines
Scheunemann, Matthias,Hennig, Lothar,Funke, Uta,Steinbach, J?rg
supporting information; experimental part, p. 3448 - 3456 (2011/06/20)
Nucleophilic ring-opening reactions of three 1-aralkyl-3,4-epoxypiperidines with a series of aliphatic and aromatic amines have been investigated. Reactions in protic solvents, preferably 2-propanol, gave rise to 3-amino-piperidin-4-ols in ratios up to 20:1. Accordingly, 4- fluorobenzyltrozamicol, a highly potent ligand for the vesicular acetylcholine transporter was obtained directly from an epoxide ring opening in one step, without the need of chromatographic separation. Reactions in acetonitrile assisted by Li-salts, most suitable with LiBr, led regioselectively to trans-4-amino-piperidin-3-ols in high yields. N-Phenethyl substituted anilino-piperidinols as easily obtained by this method were converted into a series of new β-hydroxy substituted anilidopiperidines.
Effect of structure of nucleophile and substrate on the quaternization of heterocyclic amines
Zhuravlev,Verolainen,Voronchikhina
experimental part, p. 1025 - 1028 (2011/01/11)
The influence of the nature of the quaternizing agent and substrate on the quaternization of heterocyclic amines, derivatives of pyridine, ss-picoline, nicotinamide, pyridoxine, was studied. The synthesized compounds were characterized by IR spectroscopy and elemental analysis. The conclusions were made about the effect of the structure of nucleophile and substrate on the process of quaternization reaction. Pleiades Publishing, Ltd., 2010.