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Ingreso sintético a moléculas polifuncionalizadas a través de la [3+2]-cicloadición de ylidos de tiocarbonio

Franz-Lucas Haut¹, Christoph Habiger¹, Klaus Speck²

¹Institute of Organic Chemistry and Center for Molecular Biosciences, Leopold-Franzens-University Innsbruck , Innrain 80-82 , 6020 Innsbruck , Austria.

Journal of the American Chemical Society

|August 14, 2019

Resumen

Este estudio explora las reacciones de [3+2]-cicloadición utilizando ylidos tiocarbónicos, produciendo derivados versátiles de tiofeno. Las condiciones de alta presión mejoran los rendimientos para sustratos difíciles y permiten la síntesis farmacéutica.

Área de la Ciencia:

Química orgánica
Química sintética
Química medicinal

Sus antecedentes:

Los ylidos de tiocarbonio son intermediarios reactivos.
Las reacciones de cicloadición son herramientas sintéticas clave.
El acceso a los heterociclos complejos que contienen azufre es valioso.

Objetivo del estudio:

Investigar la [3+2]-cicloadición de los tiocarbonilideos con los alquenos y las alquinas.
Desarrollar vías sintéticas versátiles para los derivados del tiofeno.
Para demostrar la utilidad en la síntesis farmacéutica.

Principales métodos:

Las reacciones de [3+2]-cicloadición.
Uso de condiciones de alta presión.
Síntesis de los intermediarios de dihidro y tetrahidrotiofeno.

Principales resultados:

Cicloadición exitosa con diversos alquenos y alquinas.
Formación de productos versátiles de dihidro y tetrahidrotiofeno.
Mejoras de rendimiento de hasta el 58% bajo alta presión.
Acceso a los tiofenos, los dienos, los dendralenos y los centros vicuaternarios.

Conclusiones:

La [3+2]-cicloadición es un método poderoso para sintetizar heterociclos de azufre.
Las condiciones de alta presión mejoran el alcance y la eficiencia de la reacción.
La metodología proporciona acceso a valiosos intermediarios para el descubrimiento de fármacos, incluidos el NGB 4420 y la tenilapina.

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