Introduction of tetrazol-1-yl and 5-methyltetrazol-1-yl substituents in the phenyl ring of dibenzo-18-crown-6

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