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

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-3 H -2,1-benzoxaboroles were synthesised in 70–86% yield. Interesting hydrogen bond features were observed in the crystal la...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2017-06, Vol.49 (11), p.2435-2442
Main Authors: Kamath, Prashantha, Rajan, Ramya, Deshpande, Sudhindra H., Montgomery, Mark, Lal, Mukul
Format: Article
Language:English
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Summary: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-3 H -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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1588739