453556-96-2Relevant academic research and scientific papers
Studies on the interactions of 5-R-3-(2-pyridyl)-1,2,4-triazines with arynes: inverse demand aza-Diels-Alder reaction versus aryne-mediated domino process
Kopchuk, Dmitry S.,Nikonov, Igor L.,Khasanov, Albert F.,Giri, Kousik,Santra, Sougata,Kovalev, Igor S.,Nosova, Emiliya V.,Gundala, Sravya,Venkatapuram, Padmavathi,Zyryanov, Grigory V.,Majee, Adinath,Chupakhin, Oleg N.
, p. 5119 - 5135 (2018)
The interactions between substituted 5-R-3-(pyridyl-2)-1,2,4-triazines with in situ generated substituted aryne intermediates have been studied. The reaction afforded either inverse demand (ID) aza-Diels-Alder products or 1,2,4-triazine ring rearrangement (domino) products as major ones depending on the nature of both the substituents at the C5 position of the 1,2,4-triazine core or in the aryne moiety. The structures of the key products were confirmed based on X-ray data. Based on the density functional theoretical (DFT) studies of the Diels-Alder transition state geometries, the influence of the nature of arynes on the direction of the 1,2,4-triazine transformation has been proposed.
5-Acylmethyl-3-(2-pyridyl)-1,2,4-triazines: Synthesis and complexes with Cu(II)
Prokhorov,Kozhevnikov,Rusinov,Matern,Nikitin,Chupakhin,Eremenko,Aleksandrov
, p. 1702 - 1705 (2005)
5-Acylmethyl-3-(2-pyridyl)-1,2,4-triazines are easily prepared from accessible 3-(2-pyridyl)-1,2,4-triazine 4-oxides by reaction of the latter with acetophenone or trifluoroacetone in the presence of NaH. The compounds obtained behaved as efficient ligand
An Efficient Cyanide-Free Approach towards 1-(2-Pyridyl)isoquinoline-3-carbonitriles via the Reaction of 5-Phenacyl-1,2,4-triazines with 1,2-Dehydrobenzene in the Presence of Alkyl Nitrites
Kopchuk, Dmitry S.,Krinochkin, Alexey P.,Khasanov, Albert F.,Kovalev, Igor S.,Slepukhin, Pavel A.,Starnovskaya, Ekaterina S.,Mukherjee, Anindita,Rahman, Matiur,Zyryanov, Grigory V.,Majee, Adinath,Rusinov, Vladimir L.,Chupakhin, Oleg N.,Santra, Sougata
, p. 483 - 488 (2018)
A cyanide-free method for the preparation of 1-(2-pyridyl)isoquinoline-3-carbonitriles (3-cyanoisoquinolines) was developed. The interaction of 5-phenacyl-3-(2-pyridyl)-1,2,4-triazines with 1,2-dehydrobenzene generated in situ from anthranilic acid and an
Luminescent neutral lanthanide complexes of 5-aryl-2,2′-bipyridine-6-carboxylic acids, synthesis and properties
Krinochkin, Alexey P.,Kopchuk, Dmitry S.,Kozhevnikov, Dmitry N.
, p. 556 - 561 (2015/11/17)
Luminescent lanthanide complexes of 4-aryl-1-(2-pyridyl)-6,7-dihydro-5H-cyclopenta[c]pyridine-3-carboxylic acids and 5-tolyl-2,2′-bipyridine-6-carboxylic acid were prepared. The ligands were synthesized using the "1,2,4-triazine" methodology. In one case, the opportunity of copper complex preparation, followed by exchange of the metal cation from copper to europium to overcome synthetic difficulties, was demonstrated. The ability of tuning the properties of the complexes by means of varying the structure of the ligands was demonstrated. In particular, the introduction of the cyclopentene moiety allowed the preparation of highly soluble complexes in non-polar organic solvents.
A versatile strategy for the synthesis of functionalized 2,2′-bi- and 2,2′:6′,2′-terpyridines via their 1,2,4-triazine analogues
Kozhevnikov, Valery N.,Kozhevnikov, Dmitry N.,Nikitina, Tatiana V.,Rusinov, Vladimir L.,Chupakhin, Oleg N.,Zabel, Manfred,Koenig, Burkhard
, p. 2882 - 2888 (2007/10/03)
A general synthetic route for the synthesis of functionalized bi- and terpyridines is reported. Functionalized 1,2,4-triazene 4-oxides 7 and 8 - obtained from the reaction of hydrazones 1 with pyridine aldehydes and followed by oxidation - are functionalized by introduction of a cyano group via nucleophilic aromatic substitution. The thus-obtained 5-cyano-1,2,4-triazines 9 and 10 undergo facile inverse-electron-demand Diels-Alder reactions with enamines and alkenes to yield functionalized bi- and terpyridines, respectively. The substituent at position 6 of the 1,2,4-triazene 4-oxides must be aromatic or heteroaromatic in order to allow their facile synthesis, but other substituents and reagents may vary. Each step of the synthetic route allows diversification, which makes the approach particularly useful for the facile synthesis of a large variety of functionalized bi- and terpyridines.
Synthesis of functionalised bipyridines by sequential nucleophilic substitution of hydrogen and cycloaddition in 1,2,4-triazine rings
Kozhevnikov, Dmitry N.,Kozhevnikov, Valery N.,Nikitina, Tatiana V.,Rusinov, Vladimir L.,Chupakhin, Oleg N.,Neunhoeffer, Hans
, p. 30 - 32 (2007/10/03)
A new methodology for the synthesis of functionalised bipyridines by the direct cyanation of 3-(2-pyridyl)-1,2,4-triazine 4-oxide through nucleophilic substitution for hydrogen followed by the transformation of the 1,2,4-triazine ring into the pyridine ring by the Diels-Alder reaction and, finally, the chemical conversion of the cyano group is described.
