Synthesis and Spectral Characterization of Benzo-[6,7][1,5]diazocino[2,1-a]isoindol-12-(14H)-one Derivatives.

Jatinder Bassin,Christopher Benham,Maryam Hashemian,Madhu Goyal,Ute Gerhard,Bhavani Anagani

doi:10.3390/molecules21080967

Jatinder Bassin, Christopher Benham + Show 4 more

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https://doi.org/10.3390/molecules21080967

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Journal: Molecules (Basel, Switzerland)	Publication Date: Jul 23, 2016
Citations: 5	License type: CC BY 4.0

Affiliation: University of Hertfordshire

Abstract

A simple synthetic route affording 27%–85% yields of benzo[6,7][1,5]diazocino[2,1-a]isoindol-12(14H)-one ring systems from readily available 3-(2-oxo-2-phenylethyl) isobenzofuran-1(3H)-ones and 2-(aminomethyl)aniline starting materials in toluene and catalysed by p-toluene-sulfonic acid is developed. The 1H- and 13C-NMR spectra of the final products were assigned using a variety of one and two-dimensional NMR experiments. The distinction between the two potential isomers of the final products was made on the basis of heteronuclear multiple bond connectivity (HMBC) NMR spectra.

Highlights

In recent years the synthesis and chemistry of medium ring heterocycles has attracted considerable attention because they are often present in biologically active natural products and because of their broad pharmacological profile [1]
The general strategies towards the synthesis of eight-membered heterocycles remain an active area of research and the most common synthetic approach to construct diazocine rings involves the conventional condensation reaction of 2-aminobenzophenones
Our interest in the synthesis of heterocyclic rings fused to medium sized rings led us to envisage

Summary

Introduction

In recent years the synthesis and chemistry of medium ring heterocycles has attracted considerable attention because they are often present in biologically active natural products and because of their broad pharmacological profile [1]. Nitrogen-containing eight-membered heterocycles such as azocines and diazocines are known to exhibit a number of important biological properties [2,3,4,5]. The general strategies towards the synthesis of eight-membered heterocycles remain an active area of research and the most common synthetic approach to construct diazocine rings involves the conventional condensation reaction of 2-aminobenzophenones. This method is time-consuming, and the yield varies with different substrates. Synthetic strategies for diazocines preparation are limited [7]

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Conclusion