I.V. Galkina^a*, G.L. Takhautdinova^a, Kh.R. Khayarov^a, L.M. Yusupova^b,

O.I Gnezdilov^a, A.V. Ilyasov^c, V.I. Galkin^a

^aKazan Federal University, Kazan, 420008 Russia

^bKazan National Research Technological University, Kazan, 420015 Russia

^cTatarstan Academy of Sciences, Kazan, 420111 Russia

E-mail: ^*vig54@mail.ru

Received July 19, 2017

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Abstract

A simple and efficient procedure for synthesis of nucleophilc aromatic substitution products in benzofurazan cycle on the basis of reactions of substituted anilines with 5-chloro-6-nitrobenzofurazan has been elaborated. The obtained products have a broad spectrum of antibacterial and antimycotic  activity. The structure of compounds has been confirmed by IR-, NMR-spectroscopy and also by single-crystal X-ray analysis. Thermal stability of the products has been studied by the combined method of thermogravimetry and differential scanning calorimetry (TG-DSC).

Keywords: substituted anilines, 5-chloro-6-nitrobenzofurazan, nucleophilc aromatic substitution, synthesis, structure, heterocyclic compounds

Acknowledgments. This study was funded by the subsidy allocated to Kazan Federal University as part of the state program for increasing its competitiveness among the world's leading centers of science and education (project no. 4.5888.2017/8.9).

Figure Captions

Fig. 1. The molecular structure of product 3 in crystal.

Fig. 2. The packing of compound 3 molecules in crystal.

Fig. 3. The curve of the combined TG-DSC analysis of product 7.

Fig. 4. The NMR-spectrum of ¹Н (CDCl₃, 400 MHz).

Fig. 5. The molecular structure of product 7 in crystal.

Fig. 6. The packing of compound 7 molecules in crystal.

References

1. Kessel D., Belton J.G. Effects of 4-nitrobenzofurazans and their N-oxides on synthesis of protein and nucleic acid by murine leukemia cells. Canсer Res., 1975, vol. 35, no. 12, pp. 3735–3740.
2. Granik V.G., Grigorev N.B. Nitric Oxide (NO). A New Way to Search for Medicines. Moscow, Vuz. Kn., 2004. 360 p. (In Russian)
3. Levinson F.S., Evgen'ev M.I., Ermolaeva E.A., Efimov S.I., Falyakhov I.F., Garipov T.V., Karimova R.G. Synthesis and biological activity of substituted benzodifurazans. Pharm. Chem. J., 2003, vol. 37, no. 10, pp. 522–525. doi: 10.1023/B:PHAC.0000014855.66913.83.
4. Macphee D.G., Robert G.P., Ternai B., Ghosh P., Stephens R. Mutagenesis of 4-nitro-benzofurazans and furoxans. Chem. Biol. Interact., 1977, vol. 19, no. 1, pp. 77–90.
5. Galkina I.V., Takhautdinova G.L., Tudrii E.V., Yusupova L.M., Falyakhov I.F., Pozdeev O.K., Shulaeva M.P., Kipenskaya L.V., Sakhibullina V.G., Krivolapov D.B., Litvinov I.A., Galkin V.I., Cherkasov R.A. Synthesis, structure, and antibacterial activity of aminobenzofuroxan and aminobenzofurazan. Russ. J. Org. Chem., 2013, vol. 49, no. 4, pp. 591–597. doi: 10.1134/S1070428013040167.
6. Galkina I.V., Takhautdinova G.L., Tudrii E.V., Yusupova L.M., Krivolapov D.B., Litvinov I.A., Cherkasov R.A., Galkin V.I. Synthesis and structure of Meisenheimer adducts in nucleophilic aromatic amination of 4,6-dinitrobenzofuroxan. Russ. J. Org. Chem., 2013, vol. 49, no. 4, pp. 598–602. doi: 10.1134/S1070428013040179.
7. Galkina I.V., Tudriy E.V., Kataeva O.N., Usupova L.M., Luftmann H., Galkin V.I. An unusual reaction of triphenylphosphine with dichlorodinitrobenzofuroxan. Phosphorus, Sulfur Silicon Relat. Elem., 2009, vol. 184, no. 4, pp. 987–991. doi: 10.1080/10426500902719636.
8. Galkina I.V., Tudrii E.V., Berdnikov E.A., Yusupova L.M., Levinson F.S., Krivolapov D.B., Litvinov L.A., Cherkasov R.A., Galkin V.I. Reactions of 5,7-Dichloro-4,6-dinitrobenzofuroxane and     -furazane with Triphenylphosphine. Russ. J. Org. Chem., 2012, vol. 48, no. 5, pp. 721–727. doi: 10.1134/S1070428012050156.
9. Galkina I.V., Takhautdinova G.L., Tudriy E.V., Yusupova L.M., Sakhibullina V.G., Krivolapov D.B., Galkin V.I. Reactions of 5,7-dichloro-4,6-dinitrobenzofuroxan and 5,7-dichloro-4,6-dinitrobenzofurazan with secondary amines. Uchenye Zapiski Kazanskogo Universiteta. Seriya Estestvennye Nauki, 2013, vol. 155, no. 1, pp. 61–77. (In Russian)
10. Armagero W.L.F., Chai C.L.L. Purification of Laboratory Chemicals. Burlington, Butterwort, Heinemann, 2009. 743 p.

For citation: Galkina I.V., Takhautdinova G.L., Khayarov Kh.R., Yusupova L.M., Gnezdilov O.I., Ilyasov A.V., Galkin V.I. Synthesis, structure, and antimicrobial activity of aminated 5-chloro-6-nitrobenzofurazan with substituted anilines. Uchenye Zapiski Kazanskogo Universiteta. Seriya Estestvennye Nauki, 2017, vol. 159, no. 4, pp. 564–574. (In Russian)

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