- PII
- S0514749225010071-1
- DOI
- 10.31857/S0514749225010071
- Publication type
- Article
- Status
- Published
- Authors
- Volume/ Edition
- Volume 61 / Issue number 1
- Pages
- 88-101
- Abstract
- The products of diazotization of 2-, 3-, and 4-aminopyridin-1-oxides in the presence of TsOH, TfOH, and camphorsulfonic acid were investigated by IR, NMR, X-ray diffraction analysis, ESI/MS and MS2 spectroscopy, and B3LYP/aug-cc-pVDZ. The structures of the products and their stability during storage depend on the type of the starting aminopyridine. 4-Aminopyridin-1-oxide reacts to give stable diazonium sulfonates, and the 2-aminoisomer gives [1,2,3,5]oxotriazol[5,4-a]pyridinium-2 sulfonates. All products readily undergo reactions typical for diazonium salts. By the B3LYP/aug-cc-pVDZ method it was determined that 4-diazonium-pyridinium-1-oxide and benzoldiazonium cation have the highest stability in the series of diazonium cations of pyridine, pyridine-1-oxide and benzoldiazonium cation.
- Keywords
- аминопиридин-1-оксиды диазотирование 1-оксидопиридиндиазония сульфонаты
- Date of publication
- 09.11.2025
- Year of publication
- 2025
- Number of purchasers
- 0
- Views
- 67
References
- 1. Mo F., Dong G., Zhang Y., Wang J. Org. Biomol. Chem. 2013, 11, 1582–1593. doi 10.1039/C3OB27366K
- 2. Мокрушин В.С., Садчикова Е.В. Химия гетероциклических диазосоединений. СПб.: Проспект Науки, 2013, 183–190.
- 3. Li D., Luo Y., Onidas D., He L., Jin M., Gazeau F., Pinson J., Mangeney C. Adv. Colloid Interface Sci. 2021, 294, 102479. doi 10.1016/j.cis.2021.102479
- 4. Filimonov V.D., Krasnokutskaya E.A., Bondarev A.A. Aryl Diazonium Salts and Related Compounds Surface Chemistry and Applications. Eds. Chehimi M., Pinson J., Mousli F. Cham: Springer, 2022, 35–57. doi 10.1007/978-3-031-04398-7_2
- 5. Firth J.D., Fairlamb I.J.S. Org. Lett. 2020, 22, 7057–7059. doi 10.1021/acs.orglett.0c02685
- 6. Naidek K.P., Hoffmeister D.M., Pazinato J., Westphal E., Gallardo H., Nakamura M., Araki K., Toma H.E., Winnischofer H. Eur. J. Inorg. Chem. 2014, 7, 1150–1157. doi 10.1002/ejic.201301442
- 7. Coudret C. Synth. Commun. 1996, 26, 3543–3547. doi 10.1080/00397919608003763
- 8. Джоуль Д. Химия гетероциклических соединений, ред. Д. Джоуль, К. Милс, М: Мир, 2009, 129–131. [Joule J., Mills K., Heterocyclic Chemistry, Chichester: Wiley-Blackwell, 2009]
- 9. Breton G.W. Comput. Theor. Chem. 2018, 1133, 51–57. doi 10.1016/j.comptc.2018.04.013
- 10. Krasnokutskaya E.A., Semenischeva N.I., Filimonov V.D., Knochel P. Synthesis. 2007, 1, 81–84. doi 10.1055/s-2006-958936
- 11. Tretyakov A.N., Krasnokutskaya E.A., Gorlushko D.A., Ogorodnikov V.D., Filimonov V.D. Tetrahedron Lett. 2011, 52, 85–87. doi 10.1016/j.tetlet.2010.10.163
- 12. Krasnokutskaya E.A., Kassanova A.Z., Estaeva M.T., Filimonov V.D. Tetrahedron Lett. 2014, 55, 3771–3773. doi 10.1016/j.tetlet.2014.05.052
- 13. Kassanova A.Z., Krasnokutskaya E.A., Beisembai P.S., Filimonov V.D. Synthesis. 2016, 48, 256–262. doi 10.1055/s-0035-1560392
- 14. Санжиев А.Н., Краснокутская Е.А., Ерин К.Д., Филимонов В.Д. ЖОрХ. 2021, 57, 842–851. [Sanzhiev A.N., Krasnokutskaya E.A., Erin K.D., Filimonov V.D. Russ. J. Org. Chem. 2021, 57, 922–929.] doi 10.31857/S0514749221060069
- 15. Чудинов А.А., Краснокутская Е.А. Довбня Р.С., Огородников В.Д., Филимонова И.Л. Изв. РАН. Сер. хим. 2016, 65, 2312–2314. [Chudinov A.A., Dovbnya R.S., Krasnokutskaya E.A., Ogorodnikov V.D., Filimonova I.L. Russ. Chem. Bull. 2016, 65, 2312–2314.] doi 10.1007/s11172-016-1583-9
- 16. Санжиев А.Н., Потапова М.И., Краснокутская Е.А., Филимонов В.Д. ЖОрХ. 2020, 56, 920–926. [San-zhiev A.N., Potapova M.I., Krasnokutskaya E.A., Filimonov V.D. Russ. J. Org. Chem. 2020, 56, 1023–1028.] doi 10.31857/S0514749220060099
- 17. Filimonov V.D., Sanzhiev A.N., Gulyaev R.O., Krasnokutskaya E.A., Bondarev A.A. Chem. Heterocycl. Compd. 2022, 58, 721–726. doi 10.1007/s10593-023-03148-4
- 18. Becker H.G.O., Böttcher H., Haufe H. J. für Prakt. Chemie. 1970, 312, 433–439. doi 10.1002/prac.19703120306
- 19. Быстров Д.М., Ферштат Л.Л. Изв. РАН. Сер. хим. 2024, 73, 33–52. [Bystrov D.M., Fershtat L.L. Russ. Chem. Bull. 2024, 73, 33–52.] doi 10.1007/s11172-024-4120-2
- 20. Kondo S., Funakoshi K., Saeki S., Hamana M. Chem. Pharm. Bull. 1986, 34, 7–14. doi 10.1248/cpb.34.7
- 21. Krasnokutskaya E.A., Chudinov A.A., Filimonov V.D. Synth. 2018, 50, 1368–1372. doi 10.1055/s-0036-1591738
- 22. Minaev B.F., Bondarchuk S.V., Gîrţu M.A. J. Mol. Struc.-Theochem. 2009, 904, 14–20. doi 10.1016/j.theochem.2009.02.022
- 23. Filimonov V.D., Trusova M.Е., Postnikov P.М., Krasnokutskaya E.A., Lee Y.M., Hwang H.Y., Kim H., Chi K.W. Org. Lett. 2008, 10, 3961–3964. doi 10.1021/ol8013528
- 24. Filimonov V.D., Krasnokutskaya E.A., Kassanova A.Z., Fedorova V.A., Stankevich K.S., Naumov N.G., Bondarev A.A., Kataeva V.A. Eur. J. Org. Chem. 2019, 2019, 665–674. doi 10.1002/ejoc.201800887
- 25. Bondarev A.A., Naumov E.V, Kassanova A.Z., Krasnokutskaya E.A., Stankevich K.S., Filimonov V.D. Org. Process Res. Dev. 2019, 23, 2405–2415. doi 10.1021/acs.oprd.9b00307
- 26. Bekiarian P.G., Doyle M., Farnham W.B., Feiring A.E., Morken P.A., Roelofs M.G., Marshall W.J. J. Fluor. Chem. 2004, 125, 1187–1204. doi 10.1016/j.jfluchem.2004.05.007
- 27. Bardajı́ M., Crespo O., Laguna A., Fischer A. K. Inorg. Chim. Acta. 2000, 304, 7–16. doi 10.1016/S0020-1693(00)00052-9
- 28. Zollinger H. Diazo Chemistry I: Aromatic and Heteroaromatic Compounds, Ed. Zollinger H. Weinheim: Wiley VCH. 1994, 96–98.
- 29. Deady L.W. Synth. Comm. 1977, 7, 509–514. doi 10.1080/00397917709409270
- 30. Sheldrick G.M. Acta Cryst. 2015, A71, 3–8. doi 10.1107/S2053273314026370
- 31. Sheldrick G.M. Acta Cryst. 2015, C71, 3–8. doi 10.1107/S2053229614024218
- 32. Abramovitch R.A., Cue B.W. J. Am. Chem. Soc. 1976, 98, 1478–1486. doi 10.1021/ja00422a034
- 33. Katritzky A. R., Monro A. R. J. Chem. Soc., 1958, 150–153. doi 10.1039/JR9580000150
