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INTRODUCTION OF TETRAZOL-1-YL AND 5-METHYLTETRAZOL-1-YL SUBSTITUENTS IN THE PHENYL RING OF DIBENZO-18-CROWN-6

Vladimir A. Ostrovskii, Maryana S. Mazur, Vera V. Mikhailenko, Nikolai A. Aksenov, Alexander V. Aksenov
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Abstract


Derivatives of the macrocyclic polyether dibenzo-18-crown-6 containing tetrazol-1-yl and 5-methyltetrazol-1-yl substituents in one of the phenyl rings have been synthesized for the first time: 1-(6,7,9,10,17,18,20,21-octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecen-2-yl)-1H-tetrazole and 5-methyl-1-(6,7,9,10,17,18,20,21-octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecen-2-yl)-1H-tetrazole, respectively. The first compound was obtained by a three-component domino reaction involving an arylamino derivative of dibenzo-18-crown-6, triethyl orthoformate, and sodium azide in glacial acetic acid. The second compound was prepared by treating the appropriate acetamide with tetrachlorosilane – sodium azide system in acetonitrile.


Keywords


crown ethers; dibenzo-18-crown-6; tetrazoles

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