An Efficient Synthesis of 3-Phosphorylated Benzoxaboroles via the Pudovik Reaction

Dedicated to Prof. Dr. Michael Schmittel on the occasion of his 60^th birthday

Abstract

A simple, fast and efficient synthesis of 3-phosphorylated benzoxaboroles using the Pudovik reaction is reported. A number of diverse 3-(dialkoxyphosphoryl)-1-hydroxy-3H-2,1-benzoxaboroles were synthesised in 70–86% yield. Interesting hydrogen bond features were observed in the crystal lattice of the 5-chlorinated 3-bis(benzyl­oxy)phosphoryl derivative with both inter- and intramolecular C–H···O hydrogen bonds. Additionally, linear chains of intermolecular O–H···O hydrogen bonds were observed.

Key words

nucleophilic addition - phosphorus - boron - antifungal agents - heterocycles

• References

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