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

Автори: 
Maryna Stasevych, Viktor Zvarych, Rostyslav Musyanovych, Volodymyr Novikov and Mykhailo Vovk

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.

[1] Danilkina N., Mikhailov L. and Ivin B.: Russ. J. Org. Chem., 2006, 42, 783.
[2] Hartung J., Rosenbaum K., Beyer L. and Fernandes V.: J. Prakt. Chem., 1991, 333, 557.
[3] Zeng R.-S., Zou J.-P., Zhi S.-J, Chen J. and Shen Q.: Org. Lett., 2003, 5, 657.
[4] Manaka A., Ishii T. and Takahashi K.: Tetrahedron Lett., 2005, 46, 419.
[5] Wang X., Wang F., Quan Z. et al.: Synt. Commun., 2006, 36, 2453. 
[6] Murru S.,Singh C., Kalava V. and Patel B.: Tetrahedron, 2008, 64, 1931. 
[7] Kodomari M., Suzuki M., Tanigawa K. and Aoyoma T.: Tetrahedron Lett., 2005, 46, 5841. 
[8] Aly A., Ahmed E.  and El-Mokadam K.: J. Heterocycl. Chem., 2007, 44, 1431. 
[9] Aly A., Brown A., Ramadan M. et al.: J. Heterocycl. Chem., 2010, 47, 503. 
[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.
[12] Zhang N., Tomizawa M. and Casida J.: J. Med. Chem., 2002, 45, 2832.
[13] Walczynski K., Guryn R., Zuiderveld O. et al.: Farmaco, 2000, 55, 569.
[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. 
[18] Eweis M., Elkholy S. and Elsabee M.: Int. J. Biolog. Macromol., 2006, 38, 1. 
[19] Sriram D., Yogeeswari P., Dinakaran M. and Thirumurugan R.: J. Antimic. Chemother., 2007, 59, 1194. 
[20] Kaymakcioglu K., Rollas S. and Kartal-Aricioglu F.: Eur. J. Drug Metabol. Pharmacokin., 2003, 28, 273. 
[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. 
[23] Saeed S., Rashid N., Ali M. et al.: Eur. J. Chem., 2010, 1, 221. 
[24] Das K. and Fres. J.: Analyt. Chem., 1984, 318, 612. 
[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.
[28] Wu F., Hu M., Wu Y. et al.: Spectr. Acta, 2006, 65, 633.
[29] Yavari I. and Kowsari E.: J. Sulfur Chem., 2008, 29, 529.
[30] de Sequeira Aguiar L., Viana G., dos Santos Romualdo M. et al.: Lett. in Org. Chem, 2011, 8, 540.
[31] Gouda M., Berghot M., Shoeib A. et al.: Turk. J. Chem., 2010, 34, 651.
[32] Kurzer F.: Org. Synth. 1951, 31, 21. 
[33] Gupta A., Mishra P., Kashaw S. et al.: Eur. J. Med. Chem., 2008, 43, 749.
[34] Savel'ev V. and Loskutov V.: Chem. Heterocycl. Compd., 1989, 25, 642.
[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.
[37] Geerlings P., Langenaeker W., de Proft F. and Baeten A.: Theor. Comp. Chem., 1996, 3, 587.
[38] Thomas J. and Taylor J.: Can. J. Chem., 1986, 64, 2235.
[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.