10 research outputs found
Expeditious microwave-assisted synthesis of 5-alkoxyoxazoles from α-triflyloxy esters and nitriles.
International audienceA rapid and general access to diversely substituted 5-alkoxyoxazoles 2 (i.e., R(1), R(2) = alkyl, phenyl) from easily accessible α-triflyloxy/hydroxy esters 1 and nitriles with good yields (41-76%) is reported. The versatility of the cyclization is shown for a range of substrates with high selectivity toward triflates over mesylates and proved to be compatible with sensitive functional groups. As an illustration of this transformation, the first synthesis of the recently isolated hydroxypyridine methyl multijuguinate 4 was achieved in four steps through a hetero Diels-Alder reaction of the 5-alkoxyoxazole and acrylic acid, followed by a protodecarboxylation reaction
Thermally controlled decarboxylative [4 + 2] cycloaddition between alkoxyoxazoles and acrylic acid: expedient access to 3-hydroxypyridines.
International audienceA modified Kondrat'eva cycloaddition involving an unprecedented thermally controlled metal-free decarboxylative aromatization affords an expedient access to natural 3-hydroxypyridine/piperidine systems
Expeditious Microwave-Assisted Synthesis of 5âAlkoxyoxazoles from αâTriflyloxy Esters and Nitriles
A rapid and general access to diversely substituted 5-alkoxyoxazoles <b>2</b> (i.e., R<sup>1</sup>, R<sup>2</sup> = alkyl, phenyl) from
easily accessible α-triflyloxy/hydroxy esters <b>1</b> and nitriles with good yields (41â76%) is reported. The versatility
of the cyclization is shown for a range of substrates with high selectivity
toward triflates over mesylates and proved to be compatible with sensitive
functional groups. As an illustration of this transformation, the
first synthesis of the recently isolated hydroxypyridine methyl multijuguinate <b>4</b> was achieved in four steps through a hetero DielsâAlder
reaction of the 5-alkoxyoxazole and acrylic acid, followed by a protodecarboxylation
reaction
Metal-Free Decarboxylative Hetero-Diels-Alder Synthesis of 3-Hydroxypyridines: A Rapid Access to N-Fused Bicyclic Hydroxypiperidine Scaffolds.
International audienc
Thermally Controlled Decarboxylative [4 + 2] Cycloaddition between Alkoxyoxazoles and Acrylic Acid: Expedient Access to 3âHydroxypyridines
A modified Kondratâeva cycloaddition involving an unprecedented thermally controlled metal-free decarboxylative aromatization affords an expedient access to natural 3-hydroxypyridine/piperidine systems
Kondrat'eva ligation: Diels-Alder-based irreversible reaction for bioconjugation
International audienceDiversification of existing chemoselective ligations is required to efficiently access complex and well-defined biomolecular assemblies with unique and valuable properties. The development and bioconjugation applications of a novel Diels-Alder-based irreversible site-specific ligation are reported. The strategy is based on a Kondrat'eva cycloaddition between bioinert and readily functionalizable 5-alkoxyoxazoles and maleimides that readily react together under mild and easily tunable reaction conditions to afford a fully stable pyridine scaffold. The potential of this novel bioconjugation is demonstrated through the preparation of fluorescent conjugates of biomolecules and a novel Förster resonance energy transfer (FRET)-based probe suitable for the in vivo detection and imaging of urokinase-like plasminogen activator (uPA), which is a key protease involved in cancer invasion and metastasis
Metal-Free Decarboxylative Hetero-DielsâAlder Synthesis of 3âHydroxypyridines: A Rapid Access to <i>N</i>âFused Bicyclic Hydroxypiperidine Scaffolds
A complete
experimental and theoretical study of the thermally
controlled metal-free decarboxylative hetero-DielsâAlder (HDA)
reaction of 5-alkoxyoxazoles with acrylic acid is reported. This strategy
offers a new entry to valuable 2,6-difunctionalized 3-hydroxypyridines
from readily available 2- and 4-disubstituted 5-alkoxyoxazoles. The
reaction conditions proved compatible with, among others, ketone,
amide, ester, ether, and nitrile groups. The broad functional group
tolerance of the protocol allows a rapid and versatile access to both
hydroxyindolizidine and hydroxyquinolizidine derivatives via a pyridine
dearomatization strategy
Kondratâeva Ligation: DielsâAlder-Based Irreversible Reaction for Bioconjugation
Diversification of existing chemoselective
ligations is required
to efficiently access complex and well-defined biomolecular assemblies
with unique and valuable properties. The development and bioconjugation
applications of a novel DielsâAlder-based irreversible site-specific
ligation are reported. The strategy is based on a Kondratâeva
cycloaddition between bioinert and readily functionalizable 5-alkoxyoxazoles
and maleimides that readily react together under mild and easily tunable
reaction conditions to afford a fully stable pyridine scaffold. The
potential of this novel bioconjugation is demonstrated through the
preparation of fluorescent conjugates of biomolecules and a novel
FoÌrster resonance energy transfer (FRET)-based probe suitable
for the in vivo detection and imaging of urokinase-like plasminogen
activator (uPA), which is a key protease involved in cancer invasion
and metastasis