From Chemistry Towards Technology Step-By-Step From Chemistry Towards Technology Step-By-Step От химии к технологии шаг за шагом 2782-1900 82579 10.52957/27821900_2021_03_115 Научные статьи Scientific articles Научные статьи Method of the synthesis of 1,2,4,5-tetrakis(benzazol)benzoles Method of the synthesis of 1,2,4,5-tetrakis(benzazol)benzoles Бегунов Роман Сергеевич Begunov Roman Sergeevich begunov@bio.ac.ru

кандидат химических наук;

candidate of chemical sciences;

 Соколов Александр Андреевич Sokolov Aleksandr Andreevich Ярославский государственный медицинский университет Yaroslavl State Medical University Ярославский государственный университет им. П.Г. Демидова P.G. Demidov Yaroslavl State University Ярославский государственный технический университет Yaroslavl State Technical University 23 09 2021 23 09 2021 2 3 115 119 30 08 2021 23 09 2021 https://ystu.editorum.ru/en/nauka/article/82579/view

We developed the simple method of obtaining of 1,2,4,5-tetrakis(benzimidazolyl)benzene and 1,2,4,5-tetrakis(1H-benzotriazol-1-yl)benzene based on the substitution of all functional groups in 1,3-dichloro-4,6-dinitrobenzene under SNAr reaction conditions.

We developed the simple method of obtaining of 1,2,4,5-tetrakis(benzimidazolyl)benzene and 1,2,4,5-tetrakis(1H-benzotriazol-1-yl)benzene based on the substitution of all functional groups in 1,3-dichloro-4,6-dinitrobenzene under SNAr reaction conditions.

 reaction SNAr 1 3-dichloro-4 6-dinitrobenzene benzimidazole benzotriazole 1 2 4 5-tetrakis(benzimidazolyl)benzene 1 2 4 5-tetrakis(1H-benzotriazol-1-yl)benzene

Khramov D.M., Boydston A.J., Bielawski C.W. Highly Efficient Synthesis and Solid-State Characterization of 1,2,4,5-Tetrakis(alkyl- and arylamino)benzenes and Cyclization to Their Respective Benzobis(imidazolium) Salts. Org. Lett. 2006. V. 8. P. 1834. DOI: 10.1021/ol060349c. Khramov D.M., Boydston A.J., Bielawski C.W. Highly Efficient Synthesis and Solid-State Characterization of 1,2,4,5-Tetrakis(alkyl- and arylamino)benzenes and Cyclization to Their Respective Benzobis(imidazolium) Salts. Org. Lett. 2006. V. 8. P. 1834. DOI: 10.1021/ol060349c. Chuang C.-H., Sathiyendiran M., Tseng Y.-H., Wu J.-Y., Hsu K.-C., Hung C.-H., Wen Y.-S., Lu K.-L. Rigidity-Modulated Approach toward the Construction of Metallacycles from a Flexible Tetratopic Ligand. Organometallics. 2010. V. 29. P. 283. DOI: 10.1021/om9007604. Chuang C.-H., Sathiyendiran M., Tseng Y.-H., Wu J.-Y., Hsu K.-C., Hung C.-H., Wen Y.-S., Lu K.-L. Rigidity-Modulated Approach toward the Construction of Metallacycles from a Flexible Tetratopic Ligand. Organometallics. 2010. V. 29. P. 283. DOI: 10.1021/om9007604. Pan R.-K., Song J. L., Li G. B., Lu C.-Y., Liu S.-G. Synthesis, crystal structure, redox property, and cytotoxic activity of a dinuclearcobalt(II) complex bearing a tetradentate benzimidazole ligand. Monatshefte für Chemie. 2019. V. 150. P. 1453. DOI: 10.1007/s00706-019-02477-5. Pan R.-K., Song J. L., Li G. B., Lu C.-Y., Liu S.-G. Synthesis, crystal structure, redox property, and cytotoxic activity of a dinuclearcobalt(II) complex bearing a tetradentate benzimidazole ligand. Monatshefte für Chemie. 2019. V. 150. P. 1453. DOI: 10.1007/s00706-019-02477-5. Seillan C., Siri O. Synthesis and characterization of N-alkyl 1,3-diamino-4,6-diamidobenzenes. Tetrahedron Lett. 2009. V. 50. P. 630. DOI: 10.1016/j.tetlet.2008.11.089. Seillan C., Siri O. Synthesis and characterization of N-alkyl 1,3-diamino-4,6-diamidobenzenes. Tetrahedron Lett. 2009. V. 50. P. 630. DOI: 10.1016/j.tetlet.2008.11.089. Adams C.J., Costa R.C., Edge R., Evans D.H., Hood M.F. On the Causes of Potential Inversion in 1,2,4,5-Tetrakis(amino)benzenes. J. Org. Chem. 2010. V. 75. P. 1168. DOI: 10.1021/jo902411b. Adams C.J., Costa R.C., Edge R., Evans D.H., Hood M.F. On the Causes of Potential Inversion in 1,2,4,5-Tetrakis(amino)benzenes. J. Org. Chem. 2010. V. 75. P. 1168. DOI: 10.1021/jo902411b. Gurbuz N., Demir S., Ozdemir I., Cetinkaya B., Bruneau C. New 1,2,4,5-tetrakis-(N-imidazoliniummethyl)benzene and 1,2,4,5-tetrakis-(N-benzimidazoliummethyl)benzene salts as N-heterocyclic tetracarbene precursors: synthesis and involvement in ruthenium-catalyzed allylation reactions. Tetrahedron. 2010. V. 66. P. 1346. DOI: 10.1016/j.tet.2009.12.004. Gurbuz N., Demir S., Ozdemir I., Cetinkaya B., Bruneau C. New 1,2,4,5-tetrakis-(N-imidazoliniummethyl)benzene and 1,2,4,5-tetrakis-(N-benzimidazoliummethyl)benzene salts as N-heterocyclic tetracarbene precursors: synthesis and involvement in ruthenium-catalyzed allylation reactions. Tetrahedron. 2010. V. 66. P. 1346. DOI: 10.1016/j.tet.2009.12.004. Chen Z., Canard G., Jacquemin D., Bucher C., Giorgi M., Siri O. Hetero-Bimetallic Effect as a Route to Access Multinuclear Complexes. Inorg. Chem. 2018. V. 57. P. 12536–12542. DOI: 10.1021/acs.inorgchem.8b01466. Chen Z., Canard G., Jacquemin D., Bucher C., Giorgi M., Siri O. Hetero-Bimetallic Effect as a Route to Access Multinuclear Complexes. Inorg. Chem. 2018. V. 57. P. 12536–12542. DOI: 10.1021/acs.inorgchem.8b01466. Xie Q., Liu S., Li X., Wu Q., Luo Z., Fu X., Cao W., Lan G., Li D., Zheng W., Chen T. Dinuclearzinc (II) complexes containing (benzimidazol-2-yl)benzene that overcome drug resistance in hepatocellular carcinoma cells through induction of mitochondria fragmentation. Dalton Trans. 2014. V. 43. P. 6973. DOI: 10.1039/C4DT00198B. Xie Q., Liu S., Li X., Wu Q., Luo Z., Fu X., Cao W., Lan G., Li D., Zheng W., Chen T. Dinuclearzinc (II) complexes containing (benzimidazol-2-yl)benzene that overcome drug resistance in hepatocellular carcinoma cells through induction of mitochondria fragmentation. Dalton Trans. 2014. V. 43. P. 6973. DOI: 10.1039/C4DT00198B. Tandon S.S., Thompson L.K., Bridson J.N., Dewan J. Dinuclear Copper (II) and Cobalt (II) Complexes of the Tetradentate Ligand 1,2,4,5-Tetrakis(benzimidazol-2-yl)benzene (BTBI): Metallacyclic and Nonmetallacyclic Derivatives. X-ray Crystal Structures of [Cu2(BTBI)2Cl2][Cu2(BTBI)Cl2(DMF)4]Cl4 and [Co2(BTBI)Br4]4DMF. Inorg. Chem. 1994. V. 33. P. 54. DOI: 10.1021/ic00079a011. Tandon S.S., Thompson L.K., Bridson J.N., Dewan J. Dinuclear Copper (II) and Cobalt (II) Complexes of the Tetradentate Ligand 1,2,4,5-Tetrakis(benzimidazol-2-yl)benzene (BTBI): Metallacyclic and Nonmetallacyclic Derivatives. X-ray Crystal Structures of [Cu2(BTBI)2Cl2][Cu2(BTBI)Cl2(DMF)4]Cl4 and [Co2(BTBI)Br4]4DMF. Inorg. Chem. 1994. V. 33. P. 54. DOI: 10.1021/ic00079a011. Begunov R.S., Gopanyuk P.D., Sokolov A.A., Sakulina V.O. SNAr Reaction of 1,5-Dichloro-2,4-dinitrobenzene with S-, O-, and N-Nucleophiles. Russian Journal of Organic Chemistry. 2018. V. 54. N 6. P. 945. DOI: 10.1134/S1070428018060209. Begunov R.S., Gopanyuk P.D., Sokolov A.A., Sakulina V.O. SNAr Reaction of 1,5-Dichloro-2,4-dinitrobenzene with S-, O-, and N-Nucleophiles. Russian Journal of Organic Chemistry. 2018. V. 54. N 6. P. 945. DOI: 10.1134/S1070428018060209. Fekner T., Gallucci J., Chan M.K. Intramolecular Aromatic Nucleophilic Substitution of the Benzimidazole-Activated Nitro Group. Org. Lett. 2003. V. 5. P. 4795. DOI: 10.1021/ol035761w. Fekner T., Gallucci J., Chan M.K. Intramolecular Aromatic Nucleophilic Substitution of the Benzimidazole-Activated Nitro Group. Org. Lett. 2003. V. 5. P. 4795. DOI: 10.1021/ol035761w.