Regioselektivnost` reakcii galogenirovaniya 9-xlorpirido[1,2-a]benzimidazola

Roman Begunov; Luisa Savina

doi:10.52957/2782-1900-2024-5-2-28-36

UDC 547.82

REGIOSELEKTIVNOST` REAKCII GALOGENIROVANIYA 9-XLORPIRIDO[1,2-A]BENZIMIDAZOLA Regioselektivnost` reakcii galogenirovaniya 9-xlorpirido[1,2-a]benzimidazola

АА Аа

Published in From Chemistry Towards Technology Step-By-Step · Volume 5, Issue 2 · Pages 28–36 · Rubric: Scientific articles

DOI: https://doi.org/10.52957/2782-1900-2024-5-2-28-36

Received: 14.05.2024 Accepted: 31.05.2024 Published: 24.06.2024

Authors

Roman Begunov

Luisa Savina

Roman Begunov

Academic degree: candidate of chemical sciences

Yaroslavl State Medical University Yaroslavl

P.G. Demidov Yaroslavl State University Associate Professor · Yaroslavl

Luisa Savina

Yaroslavl State Medical University Laborant-issledovatel' · Yaroslavl

P.G. Demidov Yaroslavl State University Student · Yaroslavl

ABSTRACT

Metodami eksperimental'noy i kvantovoy himii izuchena regioselektivnost' reakcii SEAr 9-hlorpirido[1,2-a]benzimidazola. Process galogenirovaniya provodili v sernoy kislote, ispol'zuya N-bromsukcin- ili N-hlorsukcinimid. Proishodilo obrazovanie dvuh izomernyh produktov 8-Hal-9-hlorpirido[1,2-a]benzimidazola i 6-Hal-9-hlorpirido[1,2-a]benzimidazola. Preimuschestvenno vvedenie elektrofil'noy chasticy proishodilo v 8-e polozhenie geterocikla. S pomosch'yu metodov kvantovoy himii ustanovleno, chto reakciya elektrofil'nogo galogenirovaniya imela orbital'nyy kontrol'. Orientaciya vvedeniya elektrofil'noy chasticy opredelyalas' raspredeleniem granichnoy elektronnoy plotnosti v substrate, chto horosho soglasovyvalos' s eksperimental'nymi dannymi.

KEYWORDS

9-hlorpirido[1, 2-a]benzimidazol, N-galogensukcinimid, reakciya SEAr, regioselektivnost', kvantovo-himicheskoe modelirovanie, metod DFT B3LYP/6-31G**, programmnyy kompleks PC GAMESS/Firefly i ORCA 5.0.4

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1. Mayoka G., Keiser J., Häberli C., Chibale K. Structure–Activity Relationship and in Vitro Absorption, Distribution, Metabolism, Excretion, and Toxicity (ADMET) Studies of N-aryl 3-Trifluoromethyl Pyrido[1,2-a]benzimidazoles That Are Efficacious in a Mouse Model of Schistosomiasis // ACS Infect. Dis. 2019. Vol. 5. P. 418–429. DOI:https://doi.org/10.1021/acsinfecdis.8b00313.

2. Liu A., Ji R., Shen S., Cao X., Ge,Y. A ratiometric fluorescent probe for sensing sulfite based on a pyrido [1, 2 a] benzimidazole fluorophore // New Journal of Chemistry. 2017. Vol. 41, no. 18. P. 10096-10100. DOI:https://doi.org/10.1039/C7NJ02086D.

3. Gadde S., Kleynhans A., Holien J.K., Bhadbhade M., Nguyen P.L. D., Mittra R., Yu T.T., Carter D.R., Parker M.W., Marshall G.M., Cheung B.B., Kumar N. Pyrimido[1,2-a]benzimidazoles as inhibitors of oncoproteins ubiquitin specific protease 5 and MYCN in the childhood cancer neuroblastoma // Bioorg Chem. 2023. Vol. 136. No.106462. DOI:https://doi.org/10.1016/j.bioorg.2023.106462.

4. Kotovskaya S.K., Baskakova Z.M., Charushin V.N., Chupahin O.N., Belanov E.F., Bormotov N.I., Balahnin S.M., Serova O.A. Sintez i protivovirusnaya aktivnost' ftorsoderzhaschih proizvodnyh pirido[1,2-a]benzimidazolov. Him.-farm. zhurnal. 2005. T. 39, № 11. S. 12–16. DOI:https://doi.org/10.30906/0023-1134-2005-39-11-12-16

5. Arutyunyan A.A., Avakimyan Dzh.A., Stepanyan G.M. Antibakterial'nye svoystva nekotoryh policiklicheskih geterociklov na osnove pirimidina i benzimidazola // Biolog. zhurnal Armenii. 2016. Vol. 68, iss. 2. S. 88–91. URL: https://arar.sci.am/dlibra/publication/260297

6. Koo H.L., Dupont H.L. Rifaximin: A Unique Gastrointestinal-Selective Antibiotic for Enteric Diseases // Curr. Opin. Gastroenterol. 2010. Vol. 26. P. 17–25. DOI:https://doi.org/10.1097/MOG.0b013e328333dc8d.

7. Begunov R.S., Egorov D.O., Chetvertakova A.V., Savina L.I., Zubishina A.A. Antibakterial'naya aktivnost' galogen- i nitroproizvodnyh benzimidazola v otnoshenii Bacillus subtilis // Antibiotiki i himioterapiya. 2023. T. 68, № 3-4. S. 19-24. DOI:https://doi.org/10.37489/0235-2990-2023-68-3-4-19-24.

8. Andrzejewska M., Yépez-Mulia L., Cedillo-Rivera R., Tapia A., Vilpo L., Vilpo J., Kazimierczuk Z. Synthesis, antiprotozoal and anticancer activity of substituted 2- trifluoromethyl- and 2 pentafluoroethylbenzimidazoles // European Journal of Medicinal Chemistry. 2002. Vol. 37. P. 973–978. DOI:https://doi.org/10.1016/S0223-5234(02)01421-6.

9. Tkachenko P.V., Tkachenko E.V., Zhuravel' I.A., Kazmirchuk V.V., Derbisbekova U.B. Sintez i protivomikrobnaya aktivnost' 4-arilsul'fanilproizvodnyh 5-aminopirazolov // Vestnik KazNMU. 2017. №2. S. 307–311. URL: https://cyberleninka.ru/article/n/sintez-i-protivimikrobnaya-aktivnost-4-arilsulfonilproizvodnyh-5-aminopirazolov

10. Begunov R.S., Sokolov A.A., Belova V.O., Fakhrutdinov A.N., Shashkov A.S., Fedyanin I.V. Reaction of substituted pyrido[1,2-a]benzimidazoles with electrophilic agents // Tetrahedron Letters. 2015. Vol. 56, iss. 42. P. 5701–5704. DOI:https://doi.org/10.1016/j.tetlet.2015.08.014.

11. Begunov R.S., Ryzvanovich G.A., Firgang S.I. Prostoy sposob sinteza zameschennyh benzo[4,5]imidazo[1,2-a]piridinov // Zhurnal organicheskoy himii. 2004. T. 40, № 11. S. 1740-1742. DOI:https://doi.org/10.1007/s11178-005-0082-5.

12. Bogdanova D.M., Savina L.I., Begunov R.S. Sintez i funkcionalizaciya aminoproizvodnyh pirido[1,2-a]benzimidazola // Ot himii k tehnologii shag za shagom. 2022. T. 3, № 4. S. 30-38. URL: https://chemintech.ru/ru/nauka/issue/5030/view

13. Becke A. D. Density-functional thermochemistry. III. The role of exact exchange // J. Chem. Phys. 1993. Vol. 98, no. 7. P. 5648-5652. DOI:https://doi.org/10.1063/1.464913.

14. Miehlich B. A., Savin H. S., Stoll H, Preuss H. Results Obtained with the Correlation Energy Density Functionals of Becke and Lee, Yang and Parr // Chemical Physics Letters. Vol. 157, no. 3. 1989. P. 200-206. DOI:https://doi.org/10.1016/0009-2614(89)87234-3.

15. Mueller M. Fundamentals of Quantum Chemistry. Molecular Spectroscopy and Modern Electronic Structure Computation // International Journal of Molecular Sciences. Vol. 2, no. 6. P. 291-292. DOI:https://doi.org/10.3390/i2060291.

16. Granovsky A. A. Firefly version 8.8. URL: http://classic.chem.msu.su/gran/firefly/index.html

17. Neese F. The ORCA program system // Wiley Interdisciplinary Reviews: Computational Molecular Science. 2012. Vol. 2, no. 1. P. 73–78. DOI:https://doi.org/10.1002/wcms.81.

18. Fukui K., Yonezawa T., Nagata C. MO-Theoretical Approach to the Mechanism of Charge Transfer in the Process of Aromatic Substitutions // Bulletin of the Chemical Society of Japan. 1957. Vol. 27. P. 1247-1256. DOIhttps://doi.org/10.1063/1.1743986.

19. Breza M., Milata V. Quantum-chemical studies of the nitration of benzazoles // ARKIVOC. 2005. Vol. 9. P. 80–89. DOI:https://doi.org/10.3998/ark.5550190.0006.909.

20. Bode B.M., Gordon M.S. MacMolPlt: a graphical user interface for GAMESS // J. Mol. Graphics and Modeling. 1998. Vol. 16, no. 3. P. 133-138. DOI:https://doi.org/10.1016/s1093-3263(99)00002-9).

21. Zhurko G.A. Chemcraft. Version 1.6. URL: http://www.chemcraftprog.com

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GOST

Begunov R. S., Savina L. I. Regioselektivnost` reakcii galogenirovaniya 9-xlorpirido[1,2-a]benzimidazola // From Chemistry Towards Technology Step-By-Step. 2024. no. 2. pp. 28-36. DOI: https://doi.org/10.52957/2782-1900-2024-5-2-28-36. (Date of access 25.10.2026).

MLA

Roman Begunov, Savina L. I.. "Regioselektivnost` reakcii galogenirovaniya 9-xlorpirido[1,2-a]benzimidazola." From Chemistry Towards Technology Step-By-Step 5.2 (2024): 28-36. DOI: https://doi.org/10.52957/2782-1900-2024-5-2-28-36.

APA

Begunov R. S., Savina L. I. (2024). Regioselektivnost` reakcii galogenirovaniya 9-xlorpirido[1,2-a]benzimidazola. From Chemistry Towards Technology Step-By-Step, 5(2), 28-36. https://doi.org/10.52957/2782-1900-2024-5-2-28-36

Chicago

Roman Begunov, Savina L. I.. "Regioselektivnost` reakcii galogenirovaniya 9-xlorpirido[1,2-a]benzimidazola." From Chemistry Towards Technology Step-By-Step 5, no. 2 (2024): 28-36. https://doi.org/10.52957/2782-1900-2024-5-2-28-36.

WIKI

{{cite journal | author = Begunov R. S., Savina L. I. | title = Regioselektivnost` reakcii galogenirovaniya 9-xlorpirido[1,2-a]benzimidazola | journal = From Chemistry Towards Technology Step-By-Step | year = 2024 | volume = 5 | issue = 2 | pages = 28-36 | doi = 10.52957/2782-1900-2024-5-2-28-36 }}

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REGIOSELEKTIVNOST` REAKCII GALOGENIROVANIYA 9-XLORPIRIDO[1,2-A]BENZIMIDAZOLA Regioselektivnost` reakcii galogenirovaniya 9-xlorpirido[1,2-a]benzimidazola

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