Authors: Vladimir N. KOSHELEV graduated from Gubkin Moscow Institute of Petrochemical and Gas Industry in 1975. He is Vice Rector for Academic Affairs, Head of the Department of Organic Chemistry and Petroleum Chemistry of Gubkin Russian State University of Oil and Gas (National Research University). He is author of more than 320 scientific papers in the field of organic and petroleum chemistry.
E-mail: koshelev.v@gubkin.ru
Vladimir D. RYABOV graduated from Gubkin Moscow Institute of Petrochemical and Gas Industry. He is Professor of the Department of Organic Chemistry and Petroleum Chemistry of Gubkin Russian State University of Oil and Gas (National Research University). He is author of more than 180 scientific papers in the field of organic and petroleum chemistry.
E-mail: 27helga72@mail.ru
Zoya P. BELOUSOVA graduated from Kuibyshev State University in 1975, she is Candidate of Chemical Sciences, assistant professor of the Department of Geology of Organic, Bioorganic and Medicinal Chemistry of the Samara National Research University named after S.P. Korolyov. She is specialist in the field of organic chemistry and chemistry of natural compounds. She is author of more than 80 scientific publications.
E-mail: zbelousova@mail.ru
Abstract: Sulfonyl-substituted derivatives of imidazole, 1,2,4-triazole, benzimidazole, benzotriazole have been synthesized and characterized by IR and NMR 1H-spectroscopy. It is shown that the interaction of azoles with methane and benzenesulfonic acid chlorides in the presence of an organic base gives rise to the 1H-isomers of imidazole and benzimidazole, the 4H isomer of 1,2,4-triazole and the 2H-isomer of benzotriazole. The presence in the NMR 1H-spectrum of PhSO2-4-1,2,4-Tri singlet in the region of 8.31 ppm. confirmed, that the compound is a 4H-isomer. In the NMR 1Н MeSO2-2-BzTri spectrum, a doublet of doublets is present in the regions of 7.43 and 7.91 ppm. 1H-Isomers of 1,2,4-triazole and benzotriazole and their symmetrical analogues differ in dipole moment and lipophilicity. The information obtained will help explain the mechanism of their biological action
Index UDK: 547.56; 547.584
Keywords: heterocycles, 1-(phenylsulfonyl)-1Н-imidazole, 1-(methylsulfonyl)-1Н-benzimidazole, 4-(phenylsulfonyl)-1Н-1,2,4-1,2,4-triazole, 2-(methylsulfonyl)-1Н-benzotriazole, lipophilicity, dipole moment
Bibliography:
1. Zinchenko V.A. Himicheskaja zaschita rastenii: sredstva, tehnologioga i ekologicheskaja bezopasnost [Chemical protection of plants: means, technology and environmental safety]. М.: KolosS, 2012, 127 p. (in Russian).
2. Krasovitsky B.M., Bolotin B.M. Organischeskie lubimofori [Organic phosphors]. M.: Che- mistry, 1984, 334 p. (in Russian).
3. Kozinsky V.A., Rubinov I.I. Issledovaniya v riady 2aril-benzotriazolov. Voprosy khimii i khi-micheskoy tekhnologii. Khar’kov [Studies in the series 2-aryl-benzotriazoles], 1973, vyp. 31, p. 7-14.
4. Yujie Ren, Fanhong Wu, Chunfeng Shu, Ma Liu Synthesis and Potent Biological Activity of 1-Sulfonyl Substituted Imidazole and benzo[d]imidazole Compounds. Advanced Materials Research, 2011, vol. 236-238, p. 2570-2573.
5. Motoshi Yamauchi, Tomoya Miura, Masahiro Murakami Preparation of 2-sulfonyl-1,2,3-triazolez by bace-promoted 1,2-rearrangement of a sulfonyl group. Heterocycles. 2010, vol. 80, no. 1, p. 177-181.
6. Staab H.A. Synthesen mit heterocyclischen Amiden (azoliden). Angew.Chem. 1962, no. 74, p. 407-423.
7. Gilchrist T.L. Heterocyclic chemistry. M.: Mir, 1996, 464 p.
8. Alan R. Katritzky, Xiangfu Lan, Olga V. Denisko Properties and Synthetic Utility of N-Substituted Benzotriazoles. Chem. Rev., 1998, no. 98, p. 409-548.
9. Spartan’10. Evaluation version. Wavefunction, Inc., Irvine (CA), 2010.
10. http://www.vcclab.org/lab/alogps/
11. Belousova Z.P., Selezneva E.S. Antibacterial activity and phisico-chemical propertoes of sulfoasids benzoazolides. Vestnic of Samara State University, 2007, t. 47, no. 7, p. 6-11 (in Russian
12. Selezneva E.S., Belousova Z.P., Ten’gaev E.I. i dr. Synthesis and biological activity of triazolides. Pharmaceutical Chemistry Journal, 2003, Т. 37, No 8, pp. 14-17. (in Russian).
13. Potapova I.A., Purygin P.P., Lipatov I.S. i dr. Synthesis and biological activity of aliphatic and aromatic azolides. Pharmaceutical Chemistry Journal, 2001, vol. 35, no. 11, p. 5-7 (in Russian).
14. Traven V.F., Schekotikhin A.E. Praktikum po organicheskoy khimii. М.: Binom, Laboratoriya znaniy, 2014, 592 p. (in Russian).
15. Staab H.A. Synthesen mit heterocyclischen Amiden (azoliden). Angew.Chem., 1962, no. 74, p. 407-423.