Boronic acids are extremely valuable compounds that have applications in
medicinal, and materials chemistry, and also as cross-coupling agents in synthetic
chemistry. Boronic acids often function as inhibitors for various enzymes due to their
unique electronic and physicochemical properties. B-hydroxy-1,2-oxaborolanes
(benzoboroxoles) are a class of cyclic boronic acid derivatives and are highly important
organic synthons because of their structural stability and their ability to undergo
important C-C bond forming reactions such as Suzuki cross coupling. Several of these
cyclic boronic acids are found to possess excellent pharmacological properties as
antifungal, antimalarial and anti-inflammatory agents. However, the existing literature
methodologies for the synthesis of highly functionalized benzoboroxoles are difficult and
often are not suitable for large scale synthesis.
We have been working on the development of novel synthetic methodologies for
the synthesis of functionalized benzoxaboroles as potential therapeutic agents.
Previously, we have synthesized several benzoxaboroles employing Baylis-Hillman,
Barbier allylation, and Passerini reaction protocols. In continuation of our interest on the
development of structurally diverse benzoboroxoles, we synthesized several novel
derivatives starting from 2-formylphenylboronic acid utilizing aldol reaction as the key
step. Our studies in this area including the synthesis and structural characterization data
will be presented.
University of Minnesota M.S. thesis. October 2012. Major: Chemistry. Advisor: Prof. Paul Kiprof. 1 computer file (PDF); iv, 61 pages, appendices I-V.
Walsh, Peggy Jo.
Synthesis and biological evaluation of functionalized benzoxaboroles as potential antimicrobial agents.
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