Reaction of hydroxylated naphtoquinones/antraquinones with pentafluoropyridine.

Khalil Beyki,Reza Haydari,Malek Taher Maghsoodlou

doi:10.1186/s40064-016-1708-5

Abstract

In this study, the reaction of pentafluoropyridine with hydroxylated naphtoquinones and hydroxylated antraquinones was investigated under basic conditions in DMF. One or two hydroxyl group in naphtoquinones and antraquinones react with pentafluoropyridine to give mono and di-tetrafluoropyridyl naphtoquinones/antraquinones. All the compounds were characterized using 1H, 13C and 19F-NMR spectroscopy.

Highlights

Organofluorine compounds have been used as building blocks in the pharmaceutical industry and in material science due to their unique properties (Matthew et al 2010)
The reactions of pentafluoropyridine with nucleophiles occurs in the most activated 4-position of pentafluoropyridine to give products arising from the substitution of fluorine, located para to ring nitrogen to give a range of 4-substituted tetrafluoropyridine systems (Mark et al 2012)
We reported the synthesis of 4-substituted 2,3,5,6-tetrafluoropyridine derivatives by the reaction of pentafluoropyridine with malononitrile, 1-tetrazole-5-thiol, and piperazine (Beyki et al 2015)

Summary

Introduction

Organofluorine compounds have been used as building blocks in the pharmaceutical industry and in material science due to their unique properties (Matthew et al 2010). The reactions of pentafluoropyridine with nucleophiles occurs in the most activated 4-position of pentafluoropyridine to give products arising from the substitution of fluorine, located para to ring nitrogen to give a range of 4-substituted tetrafluoropyridine systems (Mark et al 2012). Results and discussion The reaction of pentafluoropyridine 1 with an equivalent of 5,8-dihydroxynaphthalene-1,4-dione 2 in the presence of potassium carbonate in DMF gave a mixture of two products, 2a and 2b arising from the displacement of the 4-fluor pyridine ring with naphtoquinones.

Results

Conclusion