2 research outputs found
Chalcones, a Privileged Scaffold: Highly Versatile Molecules in [4+2] Cycloadditions
Este documento es una revisión sobre el uso de las chalcones como bloques de construcción en la síntesis de moléculas complejas, vía una cicloadición [4+2] de Diels-AlderChalcones are aromatic ketones found in nature as
the central core of many biological compounds. They have a
wide range of biological activity and are biogenetic precursors
of other important molecules such as flavonoids. Their
pharmacological relevance makes them a privileged scaffold,
advantageous for seeking alternative therapies in medicinal
chemistry. Due to their structural diversity and ease of
synthesis, they are often employed as building blocks for
chemical transformations. Chalcones have a carbonyl conjugated
system with two electrophilic centers that are
commonly used for nucleophilic additions, as described in
numerous articles. They can also participate in Diels-Alder
reactions, which are [4+2] cycloadditions between a diene
and a dienophile. This microreview presents a chronological
survey of studies on chalcones as dienes and dienophiles in
Diels-Alder cycloadditions. Although these reactions occur in
nature, isolation of chalcones from plants yields very small
quantities. Contrarily, synthesis leads to large quantities at a
low cost. Hence, novel methodologies have been developed
for [4+2] cycloadditions, with chalcones serving as a 2π or
4π electron system.Secretaría de Investigación y Estudios Avanzados de la UAEMex.
CONACYT
PRODEP
DAIP, Universidad de Guanajuat
Synthesis of 4,5,6,7-tetrahydrobenzoxazol-2-ones by a highly regioselective Diels-Alder cycloaddition of exo-oxazolidin-2-one dienes with chalcones
En este trabajo se describe la reactividad química de derivados de chalconas y dienos exo heterocíclicos, obteniéndose una serie de compuestos los cuales fueron caracterizados y rigurosamente identificados, demostrando de esta manera la conducta de estas moléculas en ambientes controlados.The synthesis of novel of 4,5,6,7-tetrahydrobenzoxazol-2-ones is herein reported. They were obtained in moderate to good yields by a highly regio- and stereoselective Diels-Alder cycloaddition of N-substituted exo-oxazolidin-2-one dienes with chalcones or bis-chalcones as dienophilesSecretaría de Investigación y Estudios Avanzados de la Universidad Autónoma del Estado de Méxic