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A synthetic strategy for the preparation of alkoxy‐functionalized bis‐1,2,4‐triazinyl‐2,6‐pyridines

Journal Article · · Journal of Heterocyclic Chemistry
DOI:https://doi.org/10.1002/jhet.4828· OSTI ID:2575906
 [1];  [1]
  1. Tennessee Technological Univ., Cookeville, TN (United States)
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Heteroaryl-1,2,4-triazine complexants are commonly utilized in separation science for the selective chelation of minor An from Ln in simulated high-level waste. Furthermore, to facilitate access to relevant chemical entities for hypothesis-driven inquiry toward improved separations performance, a synthetic method to construct various alkoxy-complexant derivatives was required. In this work, a convergent synthetic strategy for the production of 3,3′- and 4,4′-tetraalkoxy-bis-1,2,4-triazinyl-2,6-pyridines from readily available starting materials via a dealkylation/alkylation/condensation approach is described. Synthetic method development, substrate scope, preliminary solubility, and hydrolytic stability data in various process-relevant diluents are reported herein.

Research Organization:
Tennessee Technological Univ., Cookeville, TN (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
SC0018033
OSTI ID:
2575906
Alternate ID(s):
OSTI ID: 2367208
Journal Information:
Journal of Heterocyclic Chemistry, Journal Name: Journal of Heterocyclic Chemistry Journal Issue: 8 Vol. 61; ISSN 1943-5193; ISSN 0022-152X
Publisher:
WileyCopyright Statement
Country of Publication:
United States
Language:
English

References (30)

Pd-Catalyzed Amination of Functionalized 6-Bromo-pyridinyl-1,2,4-triazine Complexant Scaffolds: Pd-Catalyzed Amination of Functionalized 6-Bromo-pyridinyl-1,2,4-triazine Complexant Scaffolds journal June 2017
Synthesis of Bis-1,2,4-triazines via Telescoped Condensation of [1,10]-Phenanthroline-2,9-dicarbonitrile with Aromatic 1,2-Dicarbonyls: Synthesis of Bis-1,2,4-triazines via Telescoped Condensation of [1,10]-Phenanthroline-2,9-dicarbonitrile with Aromatic 1,2-Dicarbonyls journal January 2015
Efficient Preparation of Pyridinyl-1,2,4-Triazines via Telescoped Condensation with Diversely Functionalized 1,2-Dicarbonyls: Pyridinyl 1,2,4-Triazines journal July 2015
Chromatographic separation of americium from europium using bis-2,6-(5,6,7,8-tetrahydro-5,9,9-trimethyl-5,8-methano-1,2,4-benzotriazin-3-yl) pyridine journal July 2017
Next-Generation 3,3′-AlkoxyBTPs as Complexants for Minor Actinide Separation from Lanthanides: A Comprehensive Separations, Spectroscopic, and DFT Study journal March 2024
Microwave-Assisted, Metal- and Azide-Free Synthesis of Functionalized Heteroaryl-1,2,3-triazoles via Oxidative Cyclization of N-Tosylhydrazones and Anilines journal September 2022
Synthetic Access to Unsymmetric, Tridentate, Pyridyl-1,3,4-oxadiazole Complexants via Intramolecular Oxidative Annulation of Arylhydrazides with Heteroaryl Carbaldehydes journal December 2022
Pd-Catalyzed Diamination of 1,2,4-Triazinyl Complexant Scaffolds journal June 2015
Modular Approaches to Diversified Soft Lewis Basic Complexants through Suzuki–Miyaura Cross-Coupling of Bromoheteroarenes with Organotrifluoroborates journal December 2015
Synthesis of 1 H -Pyrazol-5-yl-pyridin-2-yl-[1,2,4]triazinyl Soft-Lewis Basic Complexants via Metal and Oxidant Free [3 + 2] Dipolar Cycloaddition of Terminal Ethynyl Pyridines with Tosylhydrazides journal September 2019
Synthesis of Tridentate [1,2,4] Triazinyl-Pyridin-2-yl Indole Lewis Basic Complexants via Pd-Catalyzed Suzuki–Miyaura Cross-Coupling journal October 2019
Complexation and Separation of Lanthanides(III) and Actinides(III) by Heterocyclic N-Donors in Solutions journal October 2008
Complexation and Extraction of Trivalent Actinides and Lanthanides by Triazinylpyridine N -Donor Ligands journal October 2012
Trivalent Actinide and Lanthanide Separations by Tetradentate Nitrogen Ligands: A Quantum Chemistry Study journal October 2011
Recognition of Some Lanthanides, Actinides, and Transition- and Heavy-Metal Cations by N-Donor Ligands: Thermodynamic and Kinetic Aspects journal February 2010
Highly Efficient Separation of Actinides from Lanthanides by a Phenanthroline-Derived Bis-triazine Ligand journal August 2011
Turn-On Mode Fluorescence Switch by Using Negative Photochromic Imidazole Dimer journal March 2019
The Preparation of Hydrazidines and as-Triazines Related to Substituted 2-Cyanopyridines1 journal March 1965
NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities journal October 1997
NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist journal May 2010
4,4′-Di-tert-butyl-6-(1H-tetrazol-5-yl)-2,2′-bipyridine: modification of a highly selective N-donor ligand for the separation of trivalent actinides from lanthanides journal January 2017
Convergent access to bis-1,2,4-triazinyl-2,2′-bipyridines (BTBPs) and 2,2′-bipyridines via a Pd-catalyzed Ullman-type reaction journal January 2020
Bis-(1,2,4-triazin-3-yl) ligand structure driven selectivity reversal between Am3+ and Cm3+: solvent extraction and DFT studies journal January 2021
Separation of americium from europium using 3,3′-dimethoxy-phenyl-bis-1,2,4-triazinyl-2,6-pyridine journal March 2017
SELECTIVE EXTRACTION OF Am(III) OVER Eu(III) BY 2,6-DITRIAZOLYL- AND 2,6-DITRIAZINYLPYRIDINES1 journal January 1999
An Improved Hydrolytically-Stable Bis-Triazinyl-Pyridine (BTP) for Selective Actinide Extraction journal March 2011
Influence of an Alkoxy Group on Bis-Triazinyl-Pyridines for Selective Extraction of Americium(III) journal May 2013
Separation of the Minor Actinides Americium(III) and Curium(III) by Hydrophobic and Hydrophilic BTPhen ligands: Exploiting Differences in their Rates of Extraction and Effective Separations at Equilibrium journal January 2018
Solvent Extraction Studies for the Separation of Trivalent Actinides from Lanthanides with a Triazole-functionalized 1,10-phenanthroline Extractant journal July 2020
EXTRACTION OF Am(lll) AND Eu(lll) NITRATES BY 2-6-DI-(5,6-DIPROPYL-1,2,4-TRIAZIN-3-YL)PYRIDINES 1 journal September 1999

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