сотрудник
Ярославль, Ярославская область, Россия
сотрудник
Ярославль, Ярославская область, Россия
УДК 547.791.8 Бензотриазольные соединения. Азимиды
Разработан простой метод получения 1,2,4,5-тетракис(бензимидазолил)бензола и 1,2,4,5-тетракис(1H-бензотриазол-1-ил)бензола, основанный на замещении всех функциональных групп в 1,3-дихлор-4,6-динитробензоле в условиях реакции SNAr.
Реакция SNAr, 1,3-дихлор-4,6-динитробензол, бензимидазол, бензтриазол, 1,2,4,5-тетракис(бензимидазолил)бензол, 1,2,4,5-тетракис(1H-бензотриазол-1-ил)бензол
1. 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:https://doi.org/10.1021/ol060349c.
2. 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:https://doi.org/10.1021/om9007604.
3. 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:https://doi.org/10.1007/s00706-019-02477-5.
4. Seillan C., Siri O. Synthesis and characterization of N-alkyl 1,3-diamino-4,6-diamidobenzenes. Tetrahedron Lett. 2009. V. 50. P. 630. DOI:https://doi.org/10.1016/j.tetlet.2008.11.089.
5. 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:https://doi.org/10.1021/jo902411b.
6. 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:https://doi.org/10.1016/j.tet.2009.12.004.
7. 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:https://doi.org/10.1021/acs.inorgchem.8b01466.
8. 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:https://doi.org/10.1039/C4DT00198B.
9. 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:https://doi.org/10.1021/ic00079a011.
10. 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:https://doi.org/10.1134/S1070428018060209.
11. 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:https://doi.org/10.1021/ol035761w.
