Synthesis of 1-(Adamantan-1-yl)-1H-1,2,3-Triazoles and their Salts by Adamantylation in AdOH–HClO4 and AdOH–H2SO4 Systems

Gennady T. Sukhanov, Yuliya V. Filippova, Anna G. Sukhanova, Irina Yu Bagryanskaya, Konstantin K. Bosov

Research output: Contribution to journalArticlepeer-review

Abstract

[Figure not available: see fulltext.] 1-(Adamantan-1-yl)-1H-1,2,3-triazoles and a series of 1-(adamantan-1-yl)-3-alkyl-1,2,3-triazolium salts were synthesized by regioselective adamantylation of 1,2,3-triazole derivatives. The direction of the attack by the adamantyl cation at the N-1 nitrogen atom and the regioselectivity of the processes of adamantylation and quaternization are ensured by a number of factors: the specificity of the properties of the high-acid systems AdOH–HClO4 and AdOH–H2SO4, as well as the structural aspect and high reactivity of adamantan-1-ol.

Original languageEnglish
Pages (from-to)1197-1203
Number of pages7
JournalChemistry of Heterocyclic Compounds
Volume55
Issue number12
DOIs
Publication statusPublished - 1 Dec 2019

Keywords

  • 1,2,3-triazole
  • 1-(adamantan-1-yl)-1H-1,2,3-triazole
  • 1-(adamantan-1-yl)-3-alkyl-1,2,3-triazolium salt
  • adamantan-1-ol
  • adamantylation
  • alkyl sulfate
  • perchloric acid
  • quaternization
  • regioselectivity
  • sulfuric acid
  • ACID
  • ALKYLATION
  • 4(5)-NITRO-1,2,3-TRIAZOLE
  • SELECTIVE SYNTHESIS
  • DERIVATIVES

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