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A palladium-catalyzed highly 6-endo-selective alkyl-Heck reaction of unactivated alkyl iodides provides efficient access to various 5-phenyl-1,2,3,6-tetrahydropyridine derivatives, which are important structural motifs for bioactive molecules. Mechanistic investigations reveal a hybrid palladium-radical process.
Tetrahydropyridines (THPs) have sparked notable interest as an auspicious heterocyclic moiety. Existing in distinct structural isomers including 1,2,3,4-tetrahydropyridine, 1,2,3,6-tetrahydropyridine, 2,3,4,5-tetrahydropyridine, its presence has been identified in both natural products and synthetic pharmaceutical agents.
The discovery of the neurotoxic properties of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) as well as numerous alkaloids, prompted extensive research on the synthesis and pharmacological properties of these compounds.
Two new approaches for forming 1,2,3,6-tetrahydropyridines are reported. Both reactions employ a strategic phosphate substituent on the nitrogen atom. In the presence of an additional phosphate substituent (X = P = O (OEt) 2) an anionic cascade can by triggered upon treatment with base.
1 sty 1970 · The three possible tetrahydropyridines—namely, 2,3,4,5-tetrahydropyridine or 1-piperideine, 1,2,3,4-tetrahydropyridine or 2-piperideine, and 1,2,3,6-tetrahydropyridine or 3-piperideine, are all known in the form of derivatives, but only 3-piperideine has been prepared as a stable free base.
Tetrahydropyridines (or piperideines) are heterocycles with the formula C5H9N. Three isomers exist, which differ by the location of the double bond. None of the parent species occur widely, so they are mainly of theoretical interest. Although the parent tetrahydropyridines are rare, many substituted tetrahydropyridines are known.
8 lut 2013 · 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) is a neurotoxic side product formed in the chemical synthesis of desmethylprodine opioid analgesic, which induces Parkinson disease.
