A novel tandem cyclization of condensed 2,3-dialkynylpyrazines into [1,2,3]triazolo[1′,5′;1,2]pyrido[3,4-b]pyrazines promoted by sodium azide

Gulevskaya, A. V.; Dang, Shee Van; Tyaglivy, A. S.; Пожарский, А. Ф.; Kazheva, Olga N.; Chekhlov, A. N.; D’yachenko, O. A.

doi:10.1016/j.tet.2009.11.039

Cited by 21 publications

(6 citation statements)

References 24 publications

(7 reference statements)

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“…205 The approach has been extended to the synthesis of [1,2,3]triazolo[1 0 ,5 0 ;1,2]pyrido [3,4-b]pyrazines. 206 The wide application of porphyrin derivatives led to the development of procedures intended to extend the p-system in order to tune the electronic properties of the resulting derivatives. A first report dealt with the thermal annulation of Ni II 2,3dialkynyl-5,10,15,20-tetraphenylporphyrins 226a,b to form picenoporphyrins 228a,b (Scheme 61a).…”

Section: Synthesis Of Heteroaromaticsmentioning

confidence: 99%

(Hetero)aromatics from dienynes, enediynes and enyne–allenes

et al. 2016

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The construction of aromatic rings has become a key objective for organic chemists. While several strategies have been developed for the functionalization of pre-formed aromatic rings, the direct construction of an aromatic core starting from polyunsaturated systems is yet a less explored field. The potential of such reactions in the formation of aromatics increased at a regular pace in the last few years. Nowadays, there are reliable and well-established procedures to prepare polyenic derivatives, such as dienynes, enediynes, enyne-allenes and hetero-analogues. This has stimulated their use in the development of innovative cycloaromatizations. Different examples have recently emerged, suggesting large potential of this strategy in the preparation of (hetero)aromatics. Accordingly, this review highlights the recent advancements in this field and describes the different conditions exploited to trigger the process, including thermal and photochemical activation, as well as the use of transition metal catalysis and the addition of electrophiles/nucleophiles or radical species.

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Section: Synthesis Of Heteroaromaticsmentioning

confidence: 99%

(Hetero)aromatics from dienynes, enediynes and enyne–allenes

et al. 2016

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“…Interestingly, the reaction of 6,7-dialkynylpteridines 4 with sodium azide in DMF proceeds at room temperature and leads to annelation of the triazolopyridine fragment to the starting heterocyclic system (Scheme 6) [30]. As in the previous example, the formation of two isomeric products 5 and 6 is observed.…”

Section: Methodsmentioning

confidence: 58%

“…The formation of the isomeric triazoles 6 can be presented by a similar scheme with the only difference that the role of dipolarophile will be played by the 6-alkynyl group. Under the action of sodium azide 2,3-dialkynylquinoxalines undergo a similar transformation, giving [1,2,3]triazolo[1',5':1,2]pyrido [3,4-b]quinoxalines in high yields [30]. At the same time 1-methyl-4,5-bis-(phenylethynyl)imidazole and 1,2-bis(phenylethynyl)benzene do not react with NaN 3 even after prolonged heating in DMF [30].…”

Section: Methodsmentioning

confidence: 99%

Nucleophilic cyclizations of enediynes as a method for polynuclear heterocycle synthesis

Gulevskaya

Tyaglivy

2012

Chem Heterocycl Comp

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In this review, data on the heterocyclization of enediynes, initiated by attack of an external anionic nucleophile or a nucleophilic group present in the molecule at the C≡C bond of the enediyne, are summarized.Today, the chemistry of acetylenes is experiencing its new birth. Effective methods for the synthesis of acetylenes based on the transition metal catalyzed cross-coupling of organic halides and triflates with 1-alkynes [1], alkynylboronic acids [2], alkynylstannanes [3] have been developed. The acetylenes that became accessible are used successfully for the synthesis of various carbo-and heterocyclic compounds [4][5][6][7][8][9]. In the general case addition of a nucleophilic group to a carbon-carbon triple bond leads to a hetero-ring closure according to Scheme 1, and here the formation both of endo-dig cyclization products and of heterocycles with an exocyclic C=C bond (exo-dig cyclization) is possible: exo-digR Nu X R Nu = NH, O, S, etc.; X = H or other leaving groupThe interest of researchers in the chemistry of acetylenes is also due to the discovery of a whole family of antibiotics containing a cis-3-hexene-1,5-diyne fragment in their structures and therefore called enediyne antibiotics [10][11][12][13][14]. When heated or irradiated the enediynes undergo a Bergman cyclization; they close to 1,4-arynes, which are converted in the presence of suitable donors of hydrogen atoms or other free radicals into the corresponding arenes (Scheme 2) [15]. It is supposed that the mechanism of biological action of enediyne antibiotics is based on this rather exotic transformation. At the biological level the role of hydrogen atom donor is played by a DNA molecule that leads to its destruction. This determines not only the antibacterial, but also the antiviral and anticancer activity of the enediyne antibiotics.

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“…It was reported that enediynes [( Z )‐1‐aryl‐3‐hexen‐1,5‐diynes] cyclize with sodium azide to furnish 1‐aryl‐4‐butyl and 1‐aryl‐7‐butyl benzotriazoles [15a] . Sodium azide assisted heterocyclization of enediynes was demonstrated by Gulevskaya and group [15b] . In 2013, the same group further synthesized new derivatives of fused triazoles 21, 22 and 24 by heterocyclization of enediynes (Scheme 6).…”

Section: Synthesis Of Fused 123‐triazolesmentioning

confidence: 99%

Progress in the Synthesis of Fused 1,2,3‐Triazoles

et al. 2021

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Fused heterocycles display prodigious prominence in diverse field ranging from medicinal chemistry to material science and chemical biology to catalysis. Owing to biological importance, fused 1,2,3‐triazoles have gained much attention and hence, enormous efforts on its synthesis is given by the chemists. Diverse functionalized fused polycyclic 1,2,3‐triazole heterocycles have been designed using Huisgen's thermal intramolecular cycloaddition, copper catalyzed cycloaddition, bimetallic catalytic, greener and other miscellaneous approaches. Novel methodologies that use modified substrates such as ketones, enals, β‐keto esters, olefins, enones, C−H acids etc. in place of alkynes have been developed. Herein, synthetic methodologies to construct fused 1,2,3‐triazoles are briefly discussed.

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A novel tandem cyclization of condensed 2,3-dialkynylpyrazines into [1,2,3]triazolo[1′,5′;1,2]pyrido[3,4-b]pyrazines promoted by sodium azide

Cited by 21 publications

References 24 publications

(Hetero)aromatics from dienynes, enediynes and enyne–allenes

(Hetero)aromatics from dienynes, enediynes and enyne–allenes

Nucleophilic cyclizations of enediynes as a method for polynuclear heterocycle synthesis

Progress in the Synthesis of Fused 1,2,3‐Triazoles

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