Acylation of perimidine with 1,3,5-triazines in polyphosphoric acid

Аксенов, А. В.; Боровлев, И. В.; Lyakhovnenko, A. S.; Аксенова, И. В.

doi:10.1007/s10593-007-0085-y

Cited by 15 publications

(8 citation statements)

References 3 publications

(5 reference statements)

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“…We have already shown that the 1,3,5-triazine-PPA* system is useful for the acylation and formylation of perimidines [2] and the synthesis of 1,2,3,7-tetraazapyrenes from 1H-naphtho[1,8-de][1,2,3]triazine (1,2,3-triazaphenalene) [3]. The present study is a continuation of our investigation of the synthetic scope of this system.…”

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confidence: 59%

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Reaction of 6(7)-acyl-and 6(7)-formylperimidines with 1,3,5-triazines in poly-phosphoric acid

Аксенов

Боровлев

Писаренко

et al. 2008

Chem Heterocycl Comp

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We have already shown that the 1,3,5-triazine-PPA* system is useful for the acylation and formylation of perimidines [2] and the synthesis of 1,2,3,7-tetraazapyrenes from 1H-naphtho [1,8-de][1,2,3]triazine (1,2,3-triazaphenalene) [3]. The present study is a continuation of our investigation of the synthetic scope of this system. The reaction of this system with 6(7)-acylperimidines 1a-c and 1e and 6(7)-formylperimidine (1d) was studied in present work.Since perimidines [2] and 1,2,3-triazaphenalene [3] undergo, in effect, double electrophilic attack by the system of 1,3,5-triazines 2 in PPA, we might have assumed that perimidines 1 would react analogously. Indeed, 1,3,7-triazapyrenes 3a-d were obtained in 50-65% yield upon heating 1a-d with 1,3,5-triazine (2a) in PPA. N N R N R 1 N H R N O R 1 N N N 1a-e 3a-e + 2a PPA 1, 3 a R = H, R 1 = Ph, b R = Me, R 1 = Ph, c R = R 1 = Ph, d R = R 1 = H, e R = H, R 1 = Me _______ * PPA with 86% P 2 O 5 prepared according to Uhlig [1] was used. __________________________________________________________________________________________

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confidence: 59%

“…Since perimidines [2] and 1,2,3-triazaphenalene [3] undergo, in effect, double electrophilic attack by the system of 1,3,5-triazines 2 in PPA, we might have assumed that perimidines 1 would react analogously. Indeed, 1,3,7-triazapyrenes 3a-d were obtained in 50-65% yield upon heating 1a-d with 1,3,5-triazine (2a) in PPA.…”

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confidence: 99%

Reaction of 6(7)-acyl-and 6(7)-formylperimidines with 1,3,5-triazines in poly-phosphoric acid

Аксенов

Боровлев

Писаренко

et al. 2008

Chem Heterocycl Comp

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“…Aromatization of 47 takes place by elimination of the amidine, which undergoes hydrolysis during isolation. As established somewhat earlier, at a lower temperature the perimidines are formylated (acylated) in the 1,3,5-triazine-PPA system as a result of hydrolysis of intermediates of the 46 type or their precursors [47] during isolation. This confirms indirectly the mechanism proposed for the formation of 1,3,7-triazapyrenes from perimidines.…”

Section: Triazapyrenesmentioning

confidence: 70%

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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“…The method of acylation (formylation) of perimidines, which we developed [1], is based on their reaction with 1,3,5-triazine in PPA (polyphosphoric acid). However, addition of sodium nitrite to the reaction mixture unexpectedly led to a change in the direction of the process.…”

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confidence: 99%

“…The nitroso compound 4 is then acylated with triazine 2 to give the nitroso compounds 5 which form the pentacyclic compounds 6, which are converted to the tetraazapyrenes 3a,b. 1 …”

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confidence: 99%