Synthesis of Substituted α-Trifluoromethyl Piperidinic Derivatives

Molecules. 2017 Mar 19;22(3):483. doi: 10.3390/molecules22030483.

Abstract

A comprehensive survey of pathways leading to the generation of α-trifluoromethyl monocyclic piperidinic derivatives is provided (65 references). These compounds have been synthesized either from 6-membered rings e.g., pipecolic acid or lactam derivatives by introduction a trifluoromethyl group, from pyridine or pyridinone derivatives by reduction, and from 5-membered rings e.g., prolinol derivatives by ring expansion, from linear amines by cyclization or from dienes/dienophiles by [4 + 2]-cycloaddition.

Keywords: cyclization; cycloaddition; fluorine; nitrogen heterocycles; piperidine; ring expansion; trifluoromethyl group.

Publication types

  • Review

MeSH terms

  • Amines / chemistry*
  • Cyclization
  • Cycloaddition Reaction
  • Molecular Structure
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry
  • Pyrrolidines / chemistry
  • Stereoisomerism

Substances

  • Amines
  • Piperidines
  • Pyrrolidines
  • prolinol