Error message

  • Deprecated function: Unparenthesized `a ? b : c ? d : e` is deprecated. Use either `(a ? b : c) ? d : e` or `a ? b : (c ? d : e)` in include_once() (line 1439 of /home/science2016/public_html/includes/bootstrap.inc).
  • Deprecated function: Array and string offset access syntax with curly braces is deprecated in include_once() (line 3557 of /home/science2016/public_html/includes/bootstrap.inc).
  • Deprecated function: Unparenthesized `a ? b : c ? d : e` is deprecated. Use either `(a ? b : c) ? d : e` or `a ? b : (c ? d : e)` in include_once() (line 1439 of /home/science2016/public_html/includes/bootstrap.inc).
  • Deprecated function: Array and string offset access syntax with curly braces is deprecated in include_once() (line 3557 of /home/science2016/public_html/includes/bootstrap.inc).

Synthesis of N-Benzoyl-N’-(9,10-Dioxo-9,10-Dihydroanthacen-1-yl) Thioureas and Quantum-Chemical Analysis of the Reaction Passing

Maryna Stasevych1, Viktor Zvarych1, Rostyslav Musyanovych1, Volodymyr Novikov1 and Mykhailo Vovk2
Affiliation: 
1 Lviv Polytechnic National University 12, S. Bandera str., 79013 Lviv, Ukraine; vnovikov@polynet.lviv.ua 2 Institute of Organic Chemistry of National Academy of Scieces of Ukraine, 5, Murmanska str., 02660 Kyiv, Ukraine
DOI: 
https://doi.org/10.23939/chcht08.02.135
AttachmentSize
PDF icon full_text.pdf324 KB
Abstract: 
Interaction of an order of aminoanthraquinones with benzoylisothiocyanate resulting in the formation of new N-benzoyl-N’-(9,10-dioxo-9,10-dihydroanthacen-1-yl)-thioureas was investigated. Quantum-chemical calculations using Gaussian 03W and HyperChem 8 were carried out. On their basis nucleophilic addition of aminoanthraquinones to benzoylisothiocyanate (charge control) was confirmed. A probable mechanism of nucleophilic addition was suggested. Influence of ortho-substituents on the passing of the reaction was explained. Values of absolute hardness and softness of aminoanthraquinones were calculated.
References: 

[1] Danilkina N., Mikhailov L. and Ivin B.: Russ. J. Org. Chem., 2006, 42, 783.
https://doi.org/10.1134/S1070428006060017

[2] Hartung J., Rosenbaum K., Beyer L. and Fernandes V.: J. Prakt. Chem., 1991, 333, 557.
https://doi.org/10.1002/prac.19913330404

[3] Zeng R.-S., Zou J.-P., Zhi S.-J, Chen J. and Shen Q.: Org. Lett., 2003, 5, 657.
https://doi.org/10.1021/ol030024l

[4] Manaka A., Ishii T. and Takahashi K.: Tetrahedron Lett., 2005, 46, 419.
https://doi.org/10.1016/j.tetlet.2004.11.105

[5] Wang X., Wang F., Quan Z. et al.: Synt. Commun., 2006, 36, 2453.
https://doi.org/10.1080/00397910600781208

[6] Murru S.,Singh C., Kalava V. and Patel B.: Tetrahedron, 2008, 64, 1931.
https://doi.org/10.1016/j.tet.2007.11.076

[7] Kodomari M., Suzuki M., Tanigawa K. and Aoyoma T.: Tetrahedron Lett., 2005, 46, 5841.
https://doi.org/10.1016/j.tetlet.2005.06.135

[8] Aly A., Ahmed E. and El-Mokadam K.: J. Heterocycl. Chem., 2007, 44, 1431.
https://doi.org/10.1002/jhet.5570440630

[9] Aly A., Brown A., Ramadan M. et al.: J. Heterocycl. Chem., 2010, 47, 503.
https://doi.org/10.1002/jhet.428

[10] Wu G., Qui X.-L., Zhou L. et al.: Cancer Res., 2008, 68, 83.

[11] Tomizawa M., Kagabu S., Ohno I. et al.: J. Med. Chem., 2008, 51, 4213.
https://doi.org/10.1021/jm800191a

[12] Zhang N., Tomizawa M. and Casida J.: J. Med. Chem., 2002, 45, 2832.
https://doi.org/10.1021/jm010508s

[13] Walczynski K., Guryn R., Zuiderveld O. et al.: Farmaco, 2000, 55, 569.
https://doi.org/10.1016/S0014-827X(00)00087-2

[14] Sun C. and Zhang X.: Chinese J. Struct. Chem., 2007, 26, 153.

[15] Saeed R., Khera N., Abbas M. et al.: Turk. J. Chem., 2010, 34, 335.

[16] Hassan H.: J. Serb. Chem. Soc., 1998, 63, 117.

[17] Saeed S., Rashid N., Ali M. and Hussain R.: Eur. J. Chem., 2010, 1, 200.
https://doi.org/10.5155/eurjchem.1.3.200-205.120

[18] Eweis M., Elkholy S. and Elsabee M.: Int. J. Biolog. Macromol., 2006, 38, 1.
https://doi.org/10.1016/j.ijbiomac.2005.12.009

[19] Sriram D., Yogeeswari P., Dinakaran M. and Thirumurugan R.: J. Antimic. Chemother., 2007, 59, 1194.
https://doi.org/10.1093/jac/dkm085

[20] Kaymakcioglu K., Rollas S. and Kartal-Aricioglu F.: Eur. J. Drug Metabol. Pharmacokin., 2003, 28, 273.
https://doi.org/10.1007/BF03220179

[21] Soung M., Park K., Song J. and Sung N.: J. Kor. Soc. Appl. Biol. Chem., 2008, 51, 219.

[22] Batool S. and Batool M.: Med. Chem. Res., 2007, 16, 143.
https://doi.org/10.1007/s00044-007-9017-8

[23] Saeed S., Rashid N., Ali M. et al.: Eur. J. Chem., 2010, 1, 221.
https://doi.org/10.5155/eurjchem.1.3.221-227.124

[24] Das K. and Fres. J.: Analyt. Chem., 1984, 318, 612.
https://doi.org/10.1007/BF00529123

[25] Shome S., Mazumdar M. and Haldar P.: J. Ind. Chem. Soc., 1980, 57, 139.

[26] Priewe H. and Hrynyschyn K.: Pat. DE 898896 C, Publ. Dec. 7, 1950.

[27] Savel'ev V. and Loskutov V.: Chem. Heterocycl. Compd., 1989, 25, 1066.
https://doi.org/10.1007/BF00487313

[28] Wu F., Hu M., Wu Y. et al.: Spectr. Acta, 2006, 65, 633.
https://doi.org/10.1016/j.saa.2005.12.022

[29] Yavari I. and Kowsari E.: J. Sulfur Chem., 2008, 29, 529.
https://doi.org/10.1080/17415990801911715

[30] de Sequeira Aguiar L., Viana G., dos Santos Romualdo M. et al.: Lett. in Org. Chem, 2011, 8, 540.
https://doi.org/10.2174/157017811797249281

[31] Gouda M., Berghot M., Shoeib A. et al.: Turk. J. Chem., 2010, 34, 651.

[32] Kurzer F.: Org. Synth. 1951, 31, 21.
https://doi.org/10.15227/orgsyn.031.0021

[33] Gupta A., Mishra P., Kashaw S. et al.: Eur. J. Med. Chem., 2008, 43, 749.
https://doi.org/10.1016/j.ejmech.2007.05.008

[34] Savel'ev V. and Loskutov V.: Chem. Heterocycl. Compd., 1989, 25, 642.
https://doi.org/10.1007/BF00470022

[35] Fein V.: 9,10-Antrahynoni i ih Prymenenie. Tsentr fotohimii RAN, Moskwa 1999.

[36] Rasmussen C., Villani F., Weaner L. et al.: Synthesis, 1988, 6, 456.
https://doi.org/10.1055/s-1988-27605

[37] Geerlings P., Langenaeker W., de Proft F. and Baeten A.: Theor. Comp. Chem., 1996, 3, 587.
https://doi.org/10.1016/S1380-7323(96)80054-9

[38] Thomas J. and Taylor J.: Can. J. Chem., 1986, 64, 2235.
https://doi.org/10.1139/v86-369

[39] Klopman G.: Chemical Reactivity and Reaction Paths. Wiley-Interscence Publ., New York 1977.

[40] Wang Z.: Wöhler Synthesis [in:] Hoboken N. (Ed.), Comprehensive Organic Name Reactions and Reagents. John Wiley, NY 2009, 2068-2070.

[41] Iwakura Y. and Okada H.: Can. J. Chem., 1962, 40, 2369.
https://doi.org/10.1139/v62-361