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

Authors

  • Vladimir A. Ostrovskii Saint Petersburg State Institute of Technology (Technical University), 26 Moskovsky Ave., Saint Petersburg 190013
  • Maryana S. Mazur Saint Petersburg State Institute of Technology (Technical University), 26 Moskovsky Ave., Saint Petersburg 190013
  • Vera V. Mikhailenko Saint Petersburg State Institute of Technology (Technical University), 26 Moskovsky Ave., Saint Petersburg 190013
  • Nikolai A. Aksenov North Caucasus Federal University, 1 Pushkina St., Stavropol 355009
  • Alexander V. Aksenov North Caucasus Federal University, 1 Pushkina St., Stavropol 355009

DOI:

https://doi.org/10.1007/3280

Keywords:

crown ethers, dibenzo-18-crown-6, tetrazoles

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.

Author Biography

Vladimir A. Ostrovskii, Saint Petersburg State Institute of Technology (Technical University), 26 Moskovsky Ave., Saint Petersburg 190013

д.х.н., Кафедра химии и технологии органических соединений азота

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Published

2016-11-01

Issue

Vol. 52 No. 10 (2016)

Section

Letters to the Editor