Copper(II) Bromide–Catalyzed Imino Diels–Alder Reaction: Synthesis of Pyrano[3,2‐ c ]‐ and Furo [3,2‐ c ]tetrahydroquinolines

Author: Semwal Abha   Nayak Sandip  

Publisher: Taylor & Francis Ltd

ISSN: 0039-7911

Source: Synthetic Communications, Vol.36, Iss.2, 2006-02, pp. : 227-236

Disclaimer: Any content in publications that violate the sovereignty, the constitution or regulations of the PRC is not accepted or approved by CNPIEC.

Previous Menu Next

Abstract

Copper(II) bromide is found to be an effective catalyst for the imino Diels–Alder reaction between an imine (generated in situ) and an activated alkene in acetonitrile at the ambient temperature. The reaction proceeds smoothly to afford the corresponding adduct as a mixture of chromatographically separable cis - and trans -isomers in moderate to good yields.