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

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 th...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 49; no. 11; pp. 2435 - 2442
Main Authors Kamath, Prashantha, Rajan, Ramya, Deshpande, Sudhindra H., Montgomery, Mark, Lal, Mukul
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.06.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
antifungal agents
ACID
heterocycles
HYDROGEN-BOND
BENZOBOROXOLE
nucleophilic addition
boron
BINDING
DISCOVERY
phosphorus
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Summary: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 center dot center dot center dot O hydrogen bonds. Additionally, linear chains of intermolecular O-H center dot center dot center dot O hydrogen bonds were observed.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1588739