An efficient route to 5,5″-diaryl-2,2′:6′,2″-terpyridines through 2,6-bis(1,2,4-triazin-3-yl)pyridines

Kozhevnikov, Valery N.; Kozhevnikov, Dmitry N.; Shabunina, Olga V.; Русинов, В. Л.; Чупахин, О. Н.

doi:10.1016/j.tetlet.2005.01.020

Cited by 37 publications

(19 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…22 The third strategy (route C) is a modification of route B: instead of reacting 1,10-phenanthroline-2,9-dicarbaldehyde with hydrazine, (Z)-2-(4-bromophenyl)-2-oxoacetaldehyde oxime is allowed to react with hydrazine to form (1E,2Z)-2-(4-bromophenyl)-2-hydrazonoacetaldehyde oxime; subsequent condensation with 1,10-phenanthroline-2,9-dicarbaldehyde yields the desired 4BrPhBTPhen ligand product. [23][24][25] …”

Section: Possible New Strategiesmentioning

confidence: 99%

Regioselective Synthesis of V-Shaped Bistriazinyl-phenanthrolines

et al. 2015

View full text Add to dashboard Cite

A new, regioselective synthesis of V-shaped 2,9-bis(6-(4-halophenyl)-1,2,4-triazin-3-yl)-1,10-phenanthrolines (4XPhBTPhen) ligands was developed, creating access to a simple and reliable synthesis of precursors for future supramolecular actinide complexing systems. Described is a reactant-directed regioselective synthetic method, which was found to be high yielding and reliable and yields exclusively 6,6'-phenyl BTPhen derivatives (including 4-chloro and 4-bromo) in five simple steps. Molecular and crystal structures of PhBTP and PhBTPhen products are fully determined and both were found to be in space group C2/c. Additionally, molecular and crystal structures of Z and E isomers of 2-hydrazono-2-phenylacetaldehyde oxime, a reagent in the synthetic route, reveal existence of strong intramolecular N-H···O hydrogen bonding in the Z isomer explaining its lower solubility in water.

show abstract

Section: Possible New Strategiesmentioning

confidence: 99%

Regioselective Synthesis of V-Shaped Bistriazinyl-phenanthrolines

et al. 2015

View full text Add to dashboard Cite

show abstract

“…The reaction of hydrazono-2-oximinoethane 178 with pyridine-2,6-dicarboxaldehyde led to 179 [283], however, in the presence of Pb 3 O 4 yields 4-oxide-1,2,4-triazines 180 [284] (Scheme 20.52)…”

Section: Cycloaddition Of [5 þ 1] Fragmentsmentioning

confidence: 99%

“…Several examples of a new and simple LEGO system to obtain 2,6-oligopyridines 216 [244,246,283,284,[380][381][382][383][384][385]] from 1,2,4-triazines have been described (Scheme 20.65).…”

Section: Reactions With Nucleophilic Reagentsmentioning

confidence: 99%

Six‐Membered Heterocycles: Triazines, Tetrazines and Other Polyaza Systems

Oliva¹,

Laza²,

Ocáriz³

2011

Modern Heterocyclic Chemistry

View full text Add to dashboard Cite

“…via the transformations of their 1,2,4-triazine precursors by means of aza-Diels-Alder reactions with various dienophiles; 1,7,8 Suzuki cross-coupling reactions of phenantrolines, 9 2,6-dibrompyridine, 9 or terpyridine,…”

mentioning

confidence: 99%

Unsymmetrically functionalized 5,5″-diaryl- and 5,6,5″-triaryl-2,2′:6′,2″-terpyridines: an efficient synthetic route and photophysical properties

et al. 2017

Self Cite

View full text Add to dashboard Cite

An efficient approach for the synthesis of 5,5″- or 5,6,5″-aryl substituted 2,2′:6′,2″-terpyridines, bearing an anneleted cyclopentene unit in one of the side-chain pyridine rings for the improved solubility in organic solvents, via their 1,2,4-triazine analogues has been developed. By using this approach, various aromatic substituents were introduced in the 2,2′:6′,2″-terpyridine core. Depending on the nature of the aromatic substituents, the obtained terpyridines exhibited an intense emission in a range of ca. 344–394 nm in acetonitrile solutions. For the most representative compounds, pronounced bathochromic shifts in both absorption and emission spectra were observed compared with previously reported substituted terpyridines.

show abstract

An efficient route to 5,5″-diaryl-2,2′:6′,2″-terpyridines through 2,6-bis(1,2,4-triazin-3-yl)pyridines

Cited by 37 publications

References 8 publications

Regioselective Synthesis of V-Shaped Bistriazinyl-phenanthrolines

Regioselective Synthesis of V-Shaped Bistriazinyl-phenanthrolines

Six‐Membered Heterocycles: Triazines, Tetrazines and Other Polyaza Systems

Unsymmetrically functionalized 5,5″-diaryl- and 5,6,5″-triaryl-2,2′:6′,2″-terpyridines: an efficient synthetic route and photophysical properties

Contact Info

Product

Resources

About