Facile Synthesis of 3-(Azol-1-yl)-1-adamantanecarboxylic Acids—New Bifunctional Angle-Shaped Building Blocks for Coordination Polymers

Dmitry Pavlov, Taisiya Sukhikh, Evgeny Filatov, Andrei Potapov

The Kizhner Research Center

Research output: Contribution to journal › Article

Abstract

For the first time, orthogonally substituted azole-carboxylate adamantane ligands were synthesized and used for preparation of coordination polymers. The angle-shaped ligands were prepared by the reaction of 1-adamantanecarboxylic acid and azoles (1H-1,2,4-triazole, 3-methyl-1H-1,2,4-triazole, 3,5-dimethyl-1H-1,2,4-triazole, 1H-tetrazole, 5-methyl-1H-tetrazole) in concentrated sulfuric acid. Variation of the solvent and substituents in azole rings allowed to prepare both 1D and 2D copper(II) and nickel(II) coordination polymers, [Cu₂(trzadc)₄(H₂O)_0.7]·DMF·0.3H₂O, [Cu(trzadc)₂(MeOH)]·MeOH, [Ni(trzadc)₂(MeOH)₂] and [Cu₂(mtrzadc)₃(MeOH)]⁺NO₃ ^– (trzadc-3-(1,2,4-triazol-1-yl)-adamantane-1-carboxylic acid; mtrzadc-3-(3-methyl-1,2,4-triazol-1-yl)-adamantane-1-carboxylic acid) which were structurally characterized by single crystal X-ray diffraction. Complex [Cu(trzadc)₂(MeOH)]·MeOH was shown to act as a catalyst in the Chan-Evans-Lam arylation reaction.

Original language	English
Article number	2717
Journal	Molecules
Volume	24
Issue number	15
DOIs	https://doi.org/10.3390/molecules24152717
Publication status	Published - 26 Jul 2019

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Keywords

Adamantane
Carboxylate ligands
Chain structures
Heterocyclic ligands
Metal-organic frameworks

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

Cite this

Pavlov, D., Sukhikh, T., Filatov, E., & Potapov, A. (2019). Facile Synthesis of 3-(Azol-1-yl)-1-adamantanecarboxylic Acids—New Bifunctional Angle-Shaped Building Blocks for Coordination Polymers. Molecules, 24(15), [2717]. https://doi.org/10.3390/molecules24152717

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title = "Facile Synthesis of 3-(Azol-1-yl)-1-adamantanecarboxylic Acids—New Bifunctional Angle-Shaped Building Blocks for Coordination Polymers",

abstract = "For the first time, orthogonally substituted azole-carboxylate adamantane ligands were synthesized and used for preparation of coordination polymers. The angle-shaped ligands were prepared by the reaction of 1-adamantanecarboxylic acid and azoles (1H-1,2,4-triazole, 3-methyl-1H-1,2,4-triazole, 3,5-dimethyl-1H-1,2,4-triazole, 1H-tetrazole, 5-methyl-1H-tetrazole) in concentrated sulfuric acid. Variation of the solvent and substituents in azole rings allowed to prepare both 1D and 2D copper(II) and nickel(II) coordination polymers, [Cu2(trzadc)4(H2O)0.7]·DMF·0.3H2O, [Cu(trzadc)2(MeOH)]·MeOH, [Ni(trzadc)2(MeOH)2] and [Cu2(mtrzadc)3(MeOH)]+NO3 – (trzadc-3-(1,2,4-triazol-1-yl)-adamantane-1-carboxylic acid; mtrzadc-3-(3-methyl-1,2,4-triazol-1-yl)-adamantane-1-carboxylic acid) which were structurally characterized by single crystal X-ray diffraction. Complex [Cu(trzadc)2(MeOH)]·MeOH was shown to act as a catalyst in the Chan-Evans-Lam arylation reaction.",

keywords = "Adamantane, Carboxylate ligands, Chain structures, Heterocyclic ligands, Metal-organic frameworks",

author = "Dmitry Pavlov and Taisiya Sukhikh and Evgeny Filatov and Andrei Potapov",

year = "2019",

month = jul,

day = "26",

doi = "10.3390/molecules24152717",

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AU - Pavlov, Dmitry

AU - Sukhikh, Taisiya

AU - Filatov, Evgeny

AU - Potapov, Andrei

PY - 2019/7/26

Y1 - 2019/7/26

N2 - For the first time, orthogonally substituted azole-carboxylate adamantane ligands were synthesized and used for preparation of coordination polymers. The angle-shaped ligands were prepared by the reaction of 1-adamantanecarboxylic acid and azoles (1H-1,2,4-triazole, 3-methyl-1H-1,2,4-triazole, 3,5-dimethyl-1H-1,2,4-triazole, 1H-tetrazole, 5-methyl-1H-tetrazole) in concentrated sulfuric acid. Variation of the solvent and substituents in azole rings allowed to prepare both 1D and 2D copper(II) and nickel(II) coordination polymers, [Cu2(trzadc)4(H2O)0.7]·DMF·0.3H2O, [Cu(trzadc)2(MeOH)]·MeOH, [Ni(trzadc)2(MeOH)2] and [Cu2(mtrzadc)3(MeOH)]+NO3 – (trzadc-3-(1,2,4-triazol-1-yl)-adamantane-1-carboxylic acid; mtrzadc-3-(3-methyl-1,2,4-triazol-1-yl)-adamantane-1-carboxylic acid) which were structurally characterized by single crystal X-ray diffraction. Complex [Cu(trzadc)2(MeOH)]·MeOH was shown to act as a catalyst in the Chan-Evans-Lam arylation reaction.

AB - For the first time, orthogonally substituted azole-carboxylate adamantane ligands were synthesized and used for preparation of coordination polymers. The angle-shaped ligands were prepared by the reaction of 1-adamantanecarboxylic acid and azoles (1H-1,2,4-triazole, 3-methyl-1H-1,2,4-triazole, 3,5-dimethyl-1H-1,2,4-triazole, 1H-tetrazole, 5-methyl-1H-tetrazole) in concentrated sulfuric acid. Variation of the solvent and substituents in azole rings allowed to prepare both 1D and 2D copper(II) and nickel(II) coordination polymers, [Cu2(trzadc)4(H2O)0.7]·DMF·0.3H2O, [Cu(trzadc)2(MeOH)]·MeOH, [Ni(trzadc)2(MeOH)2] and [Cu2(mtrzadc)3(MeOH)]+NO3 – (trzadc-3-(1,2,4-triazol-1-yl)-adamantane-1-carboxylic acid; mtrzadc-3-(3-methyl-1,2,4-triazol-1-yl)-adamantane-1-carboxylic acid) which were structurally characterized by single crystal X-ray diffraction. Complex [Cu(trzadc)2(MeOH)]·MeOH was shown to act as a catalyst in the Chan-Evans-Lam arylation reaction.

KW - Adamantane

KW - Carboxylate ligands

KW - Chain structures

KW - Heterocyclic ligands

KW - Metal-organic frameworks

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DO - 10.3390/molecules24152717

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ER -

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10.3390/molecules24152717