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Syntheses, geometry optimization, and electronic structure of N-and C-substituted benzonaphthyridines

  • M. Deska EMAIL logo and W. Śliwa
Published/Copyright: February 1, 2006
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Chemical Papers
From the journal Chemical Papers Volume 60 Issue 1

Abstract

Synthesis of N-and C-substituted derivatives of benzo[h][1,6]naphthyridine, bearing 2-hydroxyethyl group has been made by quaternization reaction and by condensation of corresponding methylbenzonaphthyridines with formaldehyde. For six derivatives of isomeric benzo[c][1,5]-, benzo[h][1,6]-, and benzo[f][1,7]naphthyridines the 13C NMR spectra are discussed.

For ten compounds the geometry was optimized with the AM1 and, in one case also with the ab initio 6–31G method; their effective charge values have also been calculated.

[1] Deska, M. and Śliwa, W., Chem. Pap. 56, 309 (2002). Search in Google Scholar

[2] Śliwa, W., Current Org. Chem. 7, 995 (2003). http://dx.doi.org/10.2174/138527203348662010.2174/1385272033486620Search in Google Scholar

[3] Bachowska, B. and Zujewska, T., ARKIVOC (online computer file) 2001, Part VI, p. 77–84. (Katritzky, A. R. and Rees, Ch., Editors.) 10.3998/ark.5550190.0002.607Search in Google Scholar

[4] Mianowska, B. and Śliwa, W., Spectrochim. Acta 52A, 397 (1996). 10.1016/0584-8539(95)01581-7Search in Google Scholar

[5] Peszke, J., Mianowska, B., and Śliwa, W., Spectrochim. Acta 53A, 2565 (1997). 10.1016/S1386-1425(97)00188-1Search in Google Scholar

[6] Peszke, J., Chrz»stek, L., and Śliwa, W., Chem. Pap. 58, 176 (2004). Search in Google Scholar

[7] Dondela, B. and Śliwa, W., Khim. Geterotsikl. Soedin. 2000, 944. Search in Google Scholar

[8] Peszke, J. and Śliwa, W., Spectrochim. Acta 58A, 2127 (2002). 10.1016/S1386-1425(01)00679-5Search in Google Scholar

[9] Matusiak, G., Aust. J. Chem. 52, 149 (1999). http://dx.doi.org/10.1071/C9810910.1071/C98109Search in Google Scholar

[10] Bachowska, B. and Zujewska, T., Pol. J. Chem. 70, 1324 (1996). Search in Google Scholar

[11] Chrz»stek, L., Mielniczak, M., Staroniewicz, Z., and Śliwa, W., Khim. Geterotsikl. Soedin. 1999, 1396. Search in Google Scholar

[12] Chrz»stek, L., Mianowska, B., and Śliwa, W., Aust. J. Chem. 47, 2129 (1994). http://dx.doi.org/10.1071/CH994212910.1071/CH9942129Search in Google Scholar

[13] Gurgul, E., Herman, B., Biczak, R., and Śliwa, W., Sci. Agric. Bohem. 28, 245 (1997). Search in Google Scholar

[14] Dai, W., Petersen, J. L., and Wang, K. K., J. Org. Chem. 70, 6647 (2005). http://dx.doi.org/10.1021/jo050573010.1021/jo0505730Search in Google Scholar PubMed

[15] Kavala, V., Naik, S., and Patel, B. K., J. Org. Chem. 70, 4267 (2005). http://dx.doi.org/10.1021/jo050059u10.1021/jo050059uSearch in Google Scholar PubMed

[16] Cheng, P.-N., Chiang, P.-T., and Chiu, S.-H., Chem. Commun. 2005, 1285. 10.1039/B417823HSearch in Google Scholar

[17] Xiao, J.-Ch., Ye, Ch., and Shreeve, J. M., Org. Lett. 7, 1963 (2005). http://dx.doi.org/10.1021/ol050426o10.1021/ol050426oSearch in Google Scholar PubMed

[18] Laras, Y., Quéléver, G., Garino, C., Pietrancosta, N., Sheha, M., Bihel, F., Wolfe, M. S., and Kraus, J.-L., Org. Biomol. Chem. 3, 612 (2005). http://dx.doi.org/10.1039/b415090b10.1039/B415090BSearch in Google Scholar

[19] Ray, P. Ch. and Leszczynski, J., J. Phys. Chem. 109A, 6689 (2005). 10.1021/jp050117fSearch in Google Scholar PubMed

[20] Nikitin, K. and Fitzmaurice, D., J. Am. Chem. Soc. 127, 8067 (2005). http://dx.doi.org/10.1021/ja050694h10.1021/ja050694hSearch in Google Scholar PubMed

[21] Curiel, D. and Beer, P. D., Chem. Commun., 2005, 1909. 10.1039/b418878kSearch in Google Scholar PubMed

[22] Śliwa, W. and Zujewska, T., Heterocycles 65 1713 (2005). http://dx.doi.org/10.3987/REV-05-59610.3987/REV-05-596Search in Google Scholar

[23] Holm, A. H., Moller, R., Vase, K. H., Dong, M., Norrman, K., Besenbacher, F., Pedersen, S. U., and Daasbjerg, K., New J. Chem., 29, 659 (2005). http://dx.doi.org/10.1039/b415623d10.1039/b415623dSearch in Google Scholar

[24] Dirksen, A., Kleverlaan, C. J., Reek, J. N. H., and De Cola, L., J. Phys. Chem., 109A, 5248 (2005). 10.1021/jp050207kSearch in Google Scholar PubMed

[25] de Garcia Venturini, C., Andreaus, J., Machado, V. G., and Machado, C., Org. Biomol. Chem. 3, 1751 (2005). http://dx.doi.org/10.1039/b419246j10.1039/b419246jSearch in Google Scholar PubMed

[26] Hao, E. and Vicente, M. G. H., Chem. Commun. 2005, 1306. 10.1039/B415649HSearch in Google Scholar

[27] Dewar, M. J. S., Zoebisch, E. G., Healy, E. F., and Stewart, J. J. P., J. Am. Chem. Soc. 107, 3902 (1985). http://dx.doi.org/10.1021/ja00299a02410.1021/ja00299a024Search in Google Scholar

[28] Gordon, M. S., Chem. Phys. Lett. 76, 163 (1980). http://dx.doi.org/10.1016/0009-2614(80)80628-210.1016/0009-2614(80)80628-2Search in Google Scholar

[29] Marciniak, B., Pavlyuk, V., and Deska, M., Acta Crystallogr. E58, 489 (2002). 10.1107/S1600536802005378Search in Google Scholar

[30] Peszke, J., Prace Naukowe Wyzszej Szkoły Pedagogicznej w Częstochowie (Pedagogical University Issues), Chemia i Ochrona Środowiska IV, p. 129. Częstochowa, 1999. Search in Google Scholar

[31] Peszke, J., Doctor Thesis. Military University of Technology, Warsaw, 2001. Search in Google Scholar

[32] Młochowski, J., Śliwa, W., and Achremowicz, L., Pol. J. Chem. (formerly Roczn. Chem.) 48, 787 (1974). Search in Google Scholar

[33] Hyper Chem. Release 4.5; Hypercube, Inc., Publication HC70-00-01-00 (2002). Search in Google Scholar

Published Online: 2006-2-1
Published in Print: 2006-2-1

© 2006 Institute of Chemistry, Slovak Academy of Sciences

Articles in the same Issue

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https://doi.org/10.2478/s11696-006-0006-z

Articles in the same Issue

  1. Carbon dioxide production in the oscillating Belousov—Zhabotinsky reaction with oxalic acid
  2. Potentiometric and thermodynamic studies of 3-methyl-1-phenyl-{p-[N-(pyrimidin-2-yl)-sulfamoyl]phenylazo}-2-pyrazolin-5-one and its metal complexes
  3. Spectral and electrochemical study of coordination molecules Cu4OX6L4: 3-Methylpyridine and 4-Methylpyridine Cu4OBrnCl(6−n)L4 complexes
  4. Anodic stripping voltammetric determination of lead and cadmium in soil extracts
  5. Gold and silver determination in Waters by SPHERON® Thiol 1000 preconcentration and ETAAS
  6. Syntheses, geometry optimization, and electronic structure of N-and C-substituted benzonaphthyridines
  7. Synthesis, spectral description, and lipophilicity parameters determination of phenylcarbamic acid derivatives with integrated N-phenylpiperazine moiety in the structure
  8. New methods in synthesis of acetylcholinesterase reactivators and evaluation of their potency to reactivate cyclosarin-inhibited AChE
  9. Furan-containing thiacyanine analogs and their antimicrobial activity
  10. Synthesis and biological activity of new 1,3,4-thiadiazole derivatives
  11. Synthesis and identification of immunogen medroxyprogesterone acetate residues in edible foods and preparation of the Antisera
  12. Synthesis and characterization of oligosalicylaldehyde-based epoxy resins
  13. Extracellular polysaccharides produced by acapsular mutant of Cryptococcus laurentii
  14. Liquid chromatography of synthetic polymers under limiting conditions of insolubility. I. Principle of the method
  15. Transport velocities of different particulate materials in pneumatic conveying
  16. Nitrous oxide emissions from waste incineration
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