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.