Nitrogen-Containing Organofluorine Derivatives: An Overview

Abstract

Fluorinated organic compounds, in particular those containingnitrogen atoms, are popular targets in medicinal chemistry. Theyare obtained through chemical synthesis, usually by employing small,fluorinated molecules as starting building blocks. This accountfocuses on the reactivity and synthetic applications of differenttypes of fluorinated building blocks. It summarizes recent methodologiesdeveloped in our and other laboratories for the synthesis of a varietyof nitrogen-containing organofluorine compounds. 1 Introduction 2 Fluorinated Imidoyl Halides 2.1 Reaction of Fluorinated Imidoyl Chlorides with Enolates: Synthesisof Fluorinated β-Amino Acids 2.2 Reaction of Fluorinated Imidoyl Chlorides with Sulfoxides 3 Fluorinated α-Imino Esters and Imines 3.1 Fluorinated α-Imino Esters 3.2 Fluorinated Aldimines and Ketimines 4 Fluorinated Acrylic Acid Derivatives 5 Fluorinated GEM-Difluoroalkynes 6 Fluorinated Nitriles 6.1 Synthesis of Fluorinated Uracils 6.2 Synthesis of Fluorinated Pyrimidin-2(1 H)-ones 7 Fluorinated β-Dicarbonylic Compounds 8 Miscellaneous 8.1 Tandem Ring-Closing Metathesis-Isomerization 8.2 β-Amino-α-trifluoromethyl Alcohols 9 Conclusion