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Kulikov, Oleg V.; Pavlovsky, V. I.; Андронати, С. А.

doi:10.1023/a:1024717514329

Cited by 5 publications

(6 citation statements)

References 4 publications

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“…In order to obtain evidence for the structure of the obtained macrocycle 80b it was synthesized from the syn isomer of 2-amino-5-chlorobenzophenone oxime 86. We described the chemical properties of the heterocycles 80c,d in [90] and the crystal and molecular structures of the inclusion compound of the macrocycle 80c with benzene in [91] (Fig. 2).…”

Section: Dibenzotetraazamacroheterocycles Containing Amide and Azommentioning

confidence: 99%

Dibenzotetraazamacroheterocycles: Synthesis and properties. (Review)

Kulikov

Pavlovsky

Андронати

2005

Chem Heterocycl Compd

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Data on the synthesis, complexing ability, practical applications, and biological activity of dibenzotetraazamacroheterocycles of the azacrown ether, amide, and azomethinedibenzotetraazacycloalkane types and also dibenzotetraazamacroheterocycles containing amide and azomethine fragments are classified and analyzed.At present the chemistry of nitrogen macrocycles is developing at a very high rate. Many of the compounds are highly effective extractants for metal ions [1-3], find widespread use as contrast agents for magnetic resonance imaging [4][5][6][7][8], and can also be used as precursors in the biosynthesis of certain types of alkaloids [9] and also as ion-selective [10] and fluorescent [11] receptors and as agents for the transport of ions through a liquid membrane in dialysis and electrodialysis [12,13]. Chiral macrocyclic tetraamides are used as stationary phase in liquid chromatography [14]. The potentialities of nitrogen macrocycles in theoretical and practical respects have not been exhausted, and further research in the field is promising.In the last 15 years there have been a fairly large number of monographs and reviews in which aspects of the synthesis, properties, and applications of azamacroheterocycles and their metal complexes have been touched upon [15][16][17][18][19][20][21][22][23][24][25][26]. However, there have been significantly fewer publications devoted to the various classes of dibenzotetraazamacroheterocycles (e.g., dibenzotetraaza [14]annulenes [27][28][29], macrocyclic Schiff bases based on 2,6-diformylphenols [30]). Dibenzotetraazamacroheterocycles have found use as effective extractants for metal ions and as spectrophotometric agents [31][32][33], are used in the design of new magnetic materials [34], etc. To fill the gap we considered it desirable to analyze existing published material on the synthesis, complexation, and practical applications of dibenzotetraazamacrocycles of the azacrown ether, amide, azomethine, and dibenzotetraazacycloalkane types and also dibenzotetraazamacrocycles containing amide and azomethine fragments.

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Section: Dibenzotetraazamacroheterocycles Containing Amide and Azommentioning

confidence: 99%

Dibenzotetraazamacroheterocycles: Synthesis and properties. (Review)

Kulikov

Pavlovsky

Андронати

2005

Chem Heterocycl Compd

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“…[1]. We have previously reported the synthesis [2,3], structural studies [4], chemical reactions [5], and lanthanide complex-forming abilities [6,7] of 16-and 18-member dibenzodioxatetraaza macroheterocyclic compounds of types I and II. The present report presents the results of studies of the pharmacological activities of type I and II macrocyclic compounds.…”

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Pharmacological activity of 16-and 18-member dibenzodioxatetraaza macroheterocyclic compounds

et al. 2008

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The spectrum of the biological activities (within the framework of the PASS program) that 16-and 18-member dibenzodioxatetraaza macroheterocyclic compounds might have is assessed. compounds of these classes were found to have anticonvulsant activity. 16-Member macrocyclic compounds could have antiaggregatory activity. These results lead to the conclusion that antiaggregatory and anticonvulsant substances may be found among similar macroheterocyclic compounds. 150091-150X/08/4201-0015 Compound ED 50 , mg/kg I (R 1 = Cl, R 2 = Ph) 80 [65¸92] I (R 1 = Me, R 2 = Ph) 80 [60¸98] II (R 1 = Cl, R 2 = o-Cl-C 6 H 4 ) 80 [55¸88]

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“…The mass spectrometry of quinazolines has been examined by a number of workers [5][6][7][8][9][10]. In previous work [5], we showed that the initial pathways for the decomposition of the molecular ions of quinazoline 3-oxides are accompanied by the elimination of the methyl substituent or oxygen atom, followed only then by opening of the heteroaryl ring.…”

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“…118.72 (9) 178.40 (10) data for 6-isopropyl-2,4-diphenylquinazoline [12] and a macrocycle containing quinazoline fragments [13] suggests that the presence of the N-oxide atom O (1) leads to extension of the N (1) -C (1) and N (1) -C (8) bonds, expansion of the C (1) -N (1) -C (8) bond angle, and contraction of the N (1) -C (8) -N (2) bond angle in comparison with the previously described molecules [12,13]. The molecular packing in the crystal is shown in Fig.…”

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Synthesis, crystal and molecular structure of 2-(3-chloropropyl)-6-methyl-4-phenylquinazoline 3-oxide

Kulikov

2007

Chem Heterocycl Compd

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Keywords: quinazoline, mass spectrometry, X-ray diffraction structural analysis.The acylation of oximes of 2-aminobenzophenones with different agents such as chloroacetyl chloride and 3-chloropropionyl chloride holds interest since the acyl derivatives, as shown in our previous work [1-3], are valuable intermediates for the synthesis of 16-and 18-membered dibenzodioxatetraazamacroheterocycles. In our attempt to obtain intermediates for the synthesis of 20-membered macroheterocycles, we studied the acylation of the syn isomer of the oxime of 2-amino-5-methylbenzophenone (1) using 4-chlorobutyryl chloride and found that, in the absence of base and in the presence of excess acylating agent, 2-(3-chloropropyl)-6-methyl-4-phenylquinazoline 3-oxide (3) was found in addition to the anti isomer of the 4-chlorobutyryloximine of 2-(4-chlorobutyryl)amino-5-methylbenzophenone (2). NH 2 Ph Me N OH Cl O Cl N N Me Ph Cl O O Cl NH Ph Me O N O Cl + 1 2 3 __________________________________________________________________________________________ A. B. Bogatsky Physico-

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Untitled

Cited by 5 publications

References 4 publications

Dibenzotetraazamacroheterocycles: Synthesis and properties. (Review)

Dibenzotetraazamacroheterocycles: Synthesis and properties. (Review)

Pharmacological activity of 16-and 18-member dibenzodioxatetraaza macroheterocyclic compounds

Synthesis, crystal and molecular structure of 2-(3-chloropropyl)-6-methyl-4-phenylquinazoline 3-oxide

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