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Боровлев, И. В.; Демидов, О. П.; Пожарский, А. Ф.

doi:10.1023/a:1016001321161

Cited by 8 publications

(5 citation statements)

References 6 publications

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“…A mixture with an authentic sample did not give a depressed melting point. The 1 H NMR spectrum was identical to the spectrum reported in previous work [5].…”

Section: 37-triazapyrenes 3a-e (General Method)supporting

confidence: 78%

“…The mother liquor was heated at reflux until ammonia had been completely evaporated. The crystals formed upon cooling were filtered off to give 0.105 g (47%) 8 as red-brown crystals, mp 303-305°C (ethanol) (mp 303-305°C [5]). A mixture with an authentic sample did not give a depressed melting point.…”

Section: 37-triazapyrenes 3a-e (General Method)mentioning

confidence: 99%

“…The reaction of the aldehyde 1d with 2,4,6-trimethyl-1,3,5-triazine (2b) unexpectedly led to 6-hydroxy-1,3-diazapyrene (8) instead of the corresponding triazapyrene. Diazapyrene 8 was previously obtained by another route [5]. …”

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confidence: 99%

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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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“…A mixture with an authentic sample did not give a depressed melting point. The 1 H NMR spectrum was identical to the spectrum reported in previous work [5].…”

Section: 37-triazapyrenes 3a-e (General Method)supporting

confidence: 78%

Section: 37-triazapyrenes 3a-e (General Method)mentioning

confidence: 99%

See 1 more Smart Citation

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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“…PPA with 86% P 2 O 5 content was obtained by the standard procedure of [14] (we reported previously [15] on its relatively special features in comparison with standard PPA).…”

Section: Methodsmentioning

confidence: 99%

Heterocyclic analogs of pleiadiene 76. Synthesis and tautomeric conversions of mono- and disubstituted perimidines with electron-withdrawing substituents in the naphthalene fragment

Боровлев

Пожарский

Filatova

et al. 2010

Chem Heterocycl Comp

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A series of new mono-and disubstituted perimidines with electron-withdrawing substituents in the naphthalene fragment has been synthesized. Their prototropic annular tautomerism has been investigated by 1 H NMR spectroscopy.We reported previously on the extremely slow annular prototropic tautomerism of derivatives of 2-trifluoromethylperimidine containing a formyl, acetyl, or p-toluenesulfonyl group in position 6(7) [2,3]. This phenomenon is expressed in the 1 H and 19 F NMR spectra of these compounds by the simultaneous observation of signals of both tautomers in low polarity solvents at room temperature and even on heating to 120-130 o C. It is assumed that the reason for this is the low basicity of these compounds in combination with spatial screening of both heteroatoms not only from the side of the 2-CF 3 substituent but also from the hydrogen atoms in positions 4 and 9.In the light of this it seemed of interest to investigate the prototropic tautomerism of 2-tertbutylperimidine (1) and also of the product of its 6(7)-acylation. It was expected that, not being an acceptor but being large, the tert-butyl group may hinder transfer of proton.We obtained compound 1 by the action of pivaloyl chloride on 1,8-naphthalenediamine. On acylation with acetic acid in PPA at 70-75 o C the isomeric 6(7)-and 4(9)-diacetyl derivatives of 2-tert-butylperimidine 2 and 3 were synthesized in 66 and 11% yield respectively.The 1 H NMR spectrum of 2-tert-butylperimidine (1) in CDCl 3 was unresolved. A strongly broadened peak of the ortho protons (H-4 and H-9) and a multiplet signal of the remaining aromatic protons indicated a somewhat slow prototropy. However, unlike other perimidines, the picture of the spectrum is practically

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“…Earlier, 15 it has been reported that, depending on the amount of P 2 O 5 (80 or 86%) in PPA, the regioselectivity of the reaction of compound 1 with unsaturated carboxyl ic acids can change. Therefore, a change in regioselectivi ty of the reaction of compound 1 with 1,3 dicarbonyl com pounds could have been also expected.…”

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confidence: 99%

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

et al. 2009

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Cited by 8 publications

References 6 publications

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

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

Heterocyclic analogs of pleiadiene 76. Synthesis and tautomeric conversions of mono- and disubstituted perimidines with electron-withdrawing substituents in the naphthalene fragment

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

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