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 language | English |
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Pages (from-to) | 1197-1203 |
Number of pages | 7 |
Journal | Chemistry of Heterocyclic Compounds |
Volume | 55 |
Issue number | 12 |
DOIs | |
Publication status | Published - 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