Abstract

A method of direct C-C coupling of azahetarenes with macrocycles (calix[4]arene, benzo-12crown-4, 1,5-bis(2,6-dimethylphenoxy)-3-oxapentane), based on the nucleophilic addition to unsubstituted carbon atom in azines, has been developed.

Highlights

  • Macrocyclic compounds exhibit a large variety of functions: e.q. as building inclusion compounds and selective complexing agents for metal ions

  • In the present work we have developed the method of nucleophilic

  • For the first time it is shown that calix[4]arene can be used as a nucleophilic component in this reaction both with benzo crown ethers and aryl containing podands

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Summary

Introduction

Macrocyclic compounds exhibit a large variety of functions: e.q. as building inclusion compounds and selective complexing agents for metal ions.1,2 Modification of such molecules by heterocyclic fragments makes it possible to increase their receptor ability and improve biological activity. Abstract A method of direct C-C coupling of azahetarenes with macrocycles (calix[4]arene, benzo-12crown-4, 1,5-bis(2,6-dimethylphenoxy)-3-oxapentane), based on the nucleophilic addition to unsubstituted carbon atom in azines, has been developed. We have worked out the method of one-stage modification of benzo crown ethers, their open-chain podand analogues or resorcinearenes by 1,2,4-triazine derivatives which are one of the most active azaheterocycles.5,6 In the present work we have developed the method of nucleophilic

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