Synthèse d'aryl nitronorbornènes par cycloaddition de Diels–Alder entre les aryl-nitroéthylènes et le cyclopentadiène. Justification de la stéréochimie et de la réactivité relative observées par la méthode CNDO/II. Obtention d'aryl aminonorbornènes

Abstract

Syntheses of numerous 2-aryl nitroethylenes (nitrostyrenes) have been optimized. The nitrostyrenes have been reacted with cyclopentadiene in Diels–Alder cycloadditions and the 3-aryl 2-nitronorbornenes obtained have been reduced into 3-aryl 2-aminonorbornenes. These compounds are potentially dopaminergic molecules. The stereochemistry of the adducts obtained in the Diels–Alder reaction has been determined by ¹H nmr. The stereochemistry and the relative reactivity of the nitrostyrenes versus cyclopentadiene have been confirmed by theoretical calculations based on the CNDO/II method.