Novel three-component peri-annelation reactions of carbocyclic and pyridine rings with perimidines—synthesis of 1,3-diazapyrenes and 1,3,7-triazapyrenes

Аксенов, А. В.; Lyahovnenko, Alexander S.; Аксенова, И. В.; Nadein, O. N.

doi:10.1016/j.tetlet.2008.01.064

Cited by 26 publications

(9 citation statements)

References 29 publications

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“…13 Based on the reported results, 14 we suggested that such a result is due to the reaction conditions. No formation of 1,3 diazapyrenes (4) was observed under these conditions.…”

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confidence: 88%

Synthesis of 1,3-diazapyrenes by the reaction of 1 H-perimidines with 1,3-dicarbonyl compounds

et al. 2009

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“…13 Based on the reported results, 14 we suggested that such a result is due to the reaction conditions. No formation of 1,3 diazapyrenes (4) was observed under these conditions.…”

mentioning

confidence: 88%

Synthesis of 1,3-diazapyrenes by the reaction of 1 H-perimidines with 1,3-dicarbonyl compounds

et al. 2009

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“…If there is a second nucleophilic center in the molecule, as in the case of functionalized amines, ring closure occurs [26][27][28]. Thus, the reaction of 1,3,5-triazine with ketones 13 in the presence of boron trifluoride etherate leads to isoflavones 14 [26].…”

Section: -Nacnmentioning

confidence: 99%

“…The second nucleophile in such reactions can then enter into various reactions. For example, the reaction of perimidines 12 with triazines 1 in polyphosphoric acid in the presence of ketones leads to good yields (37-75%) of 1,3-diazapyrenes 16 [28]. PPA In these cases a second nucleophilic center is formed as a result of electrophilic substitution.…”

Section: -Nacnmentioning

confidence: 99%

Use of the ring opening reactions of 1,3,5-triazines in organic synthesis (review)

Аксенов

Аксенова

2009

Chem Heterocycl Comp

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“…The first of them involves the action of the Vilsmeier reagent, formed by the vinylog of N-methylformanilide, on the perimidines 34a-c [39]. The second method is the three-component reaction between the perimidines 34a-c, 1,3,5-triazines 36a-c, and carbonyl compounds 37a-d in polyphosphoric acid, which gives a moderate yield of the corresponding 1,3-diazapyrenes 38a-j [40] (Table 1) The mechanism proposed by the authors for this unusual transformation was presented in [40]. 1,6-Diazapyrene has so far been unknown.…”

Section: Diazapyrenesmentioning

confidence: 99%

Synthesis of aza-and polyazapyrenes (Review)

Боровлев

Демидов

2008

Chem Heterocycl Comp

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Published data on methods for the synthesis of mono-, di-, tri-, and tetraazapyrenes are reviewed.It is theoretically possible to envisage about 300 isomeric aza-and polyazapyrenes with the nitrogen atoms at various positions around the periphery of the pyrene ring and also many mono-and dications with a bridging positively charged nitrogen atom. At present, according to our data, only a small number of these aromatic nitrogen heterocycles have been synthesized.The attention paid to azapyrenes is due both to theoretical aspects (aromaticity, thermodynamic stability, the mechanism of electrophilic and nucleophilic substitution, the stability of the radical-ions, etc.) and to the results of applied studies. In particular, the change of the biological activity with the inclusion of nitrogen atoms in the pyrene ring, i.e., the transition from pyrene to its aza and polyaza analogs, is of undoubted interest. Thus, whereas the monoazapyrenes found in natural subjects [1-4] exhibit mutagenic and carcinogenic activity [5] the derivatives of the most investigated 4(9)-and 2,7-diazapyrenes exhibit analgesic [6] and antiviral and antibacterial [4] activity, and also anticancer activity [8][9][10]. The mechanism of such activity is usually attributed to their known ability to act as intercalators [11][12][13][14][15][16][17][18][19][20]. Polyazapyrenes are actively used in supramolecular chemistry for the construction of molecular devices [21], compounds with topological bonding [22], molecules of the "host-guest" type [23], and macrocomplexes with the cations of transitional metals [24,25].In this review the generally accepted substitutive aza nomenclature [26] is used for these compounds, although other names were used in the earlier papers.

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Novel three-component peri-annelation reactions of carbocyclic and pyridine rings with perimidines—synthesis of 1,3-diazapyrenes and 1,3,7-triazapyrenes

Cited by 26 publications

References 29 publications

Synthesis of 1,3-diazapyrenes by the reaction of 1 H-perimidines with 1,3-dicarbonyl compounds

Synthesis of 1,3-diazapyrenes by the reaction of 1 H-perimidines with 1,3-dicarbonyl compounds

Use of the ring opening reactions of 1,3,5-triazines in organic synthesis (review)

Synthesis of aza-and polyazapyrenes (Review)

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