A facile and efficient route to one-pot synthesis of new cyclophanes using vinamidinium salts.

Nooshin Golzar,Abdolmohammad Mehranpour,Najmeh Nowrouzi

doi:10.1039/d0ra10548a

Abstract

In this study, an efficient method for the synthesis of new cyclophanes (5a–f, 6a–g) through the condensation of 1,4-phenylenedimethanamine (3) or 2,3,5,6-tetramethylbenzene-1,4-diamine (4) with 2-substituted vinamidiniums (2a–g) is described. The cyclophane derivatives are obtained in good to excellent yields in the presence of acetic acid in refluxing acetonitrile after 15 h. The structure of new compounds was validated based on their spectral data (1H NMR, 13C NMR, IR) and elemental analysis.

Highlights

The structure of a vast range of macromolecules[1] con rmed that the design and construction of macrocyclic compounds has been one of the most important reasons for improvement in supramolecular science
Since cyclophane structure is the main foundation unit in many biologically active natural products (Fig. 1),[60,61,62] their design and application is a special interest of groups working in Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr, 75169, Iran
Several methods have been reported for the synthesis of cyclophanes compounds[63,64,65,66] (Scheme 1)

Summary

Introduction

The structure of a vast range of macromolecules[1] con rmed that the design and construction of macrocyclic compounds has been one of the most important reasons for improvement in supramolecular science. An efficient method for the synthesis of new cyclophanes (5a–f, 6a–g) through the condensation of 1,4-phenylenedimethanamine (3) or 2,3,5,6-tetramethylbenzene-1,4-diamine (4) with 2substituted vinamidiniums (2a–g) is described. Paper phenylenedimethanamine (3) or 2,3,5,6-tetramethylbenzene1,4-diamine (4) by applying acetic acid in acetonitrile as solvent.

Results

Conclusion