1,4-Phenylenebis[(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methanone

Stanimir Manolov,Iliyan Ivanov

doi:10.3390/m902

Abstract

The compound named in the title was prepared from N1,N4-diphenethylterephthalamide 1. The resulting bis terephthalamide was subjected to an intramolecular α-amidoalkylation reaction with paraformaldehyde in the presence of heterogeneous catalyst TfOH/SiO2 to obtain 1,4-phenylenebis[(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methanone]. The structure of the newly synthesized compound was determined using 1H, 13C-NMR, UV, IR and mass spectral data.

Highlights

The alkaloids containing an isoquinoline skeleton are one of the largest classes of plant alkaloids which display a broad spectrum of biological activities [1]
The resulting bis terephthalamide was subjected to an intramolecular α-amidoalkylation reaction with paraformaldehyde in the presence of heterogeneous catalyst TfOH/SiO2 to obtain 1,4-phenylenebis[(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methanone]
Based on our previous experience of the application of intramolecular α-amidoalkylation for the synthesis of isoquinoline compounds, we have successfully obtained 1,4-phenylenebis[(6,7-dimethoxy-3,4-dihydroisoquinolin2(1H)-yl)methanone] using triflic acid absorbed on silica, as a green catalyst, in an intramolecular α-amidoalkylation reaction

Summary

Introduction

The alkaloids containing an isoquinoline skeleton are one of the largest classes of plant alkaloids which display a broad spectrum of biological activities [1]. Academic Editor: Norbert Haider Received: 21 April 2016; Accepted: 23 June 2016; Published: 28 June 2016 The resulting bis terephthalamide was subjected to an intramolecular α-amidoalkylation reaction with paraformaldehyde in the presence of heterogeneous catalyst TfOH/SiO2 to obtain 1,4-phenylenebis[(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methanone]. The structure of the newly synthesized compound was determined using 1H, 13C-NMR, UV, IR and mass spectral data.

Results

Conclusion