Investigation of the Mechanism of the Alkylation Reaction of 2-Methylimidazole 1,1,3,3-Tetraiodpropane-2-on by the MALDI Method

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Abstract

The mechanism of the alkylation reaction of 2-methylimidazole with 1,1,3,3-tetraiodopropan-2-one in the absence and presence an acceptor (CaCO3) of hydrogen iodide using laser desorption/ionization was studied for the first time. The composition of the reaction mixtures and possible routes for the formation of functionalized 2-methylimidazole derivatives were determined. N1 and N1,3-alkylation of 2-methylimidazole with reduced (1-iodopropan-2-one, 1,3-diiodopropan-2-one) or dehydroiodinated (2,3-diiodo-2-cyclopropen-1) forms 1,1, 3,3-tetraiodoproapan-2-one is a crucial step in the synthesis. The thermodynamic and kinetic characteristics of the reduction and dehydroiodination of 1,1,3,3-tetraiodoacetone were evaluated by quantum-chemical calculations using the [B3LYP/6-311+G(d,p)+dgdzvp) basis set.

About the authors

L. V. Klyba

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

Author for correspondence.
Email: klyba@irioch.irk.ru
ORCID iD: 0000-0002-5521-3201
Russian Federation, Favorsky St., 1, Irkutsk, 664033

E. R. Sanzheeva

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

Email: klyba@irioch.irk.ru
ORCID iD: 0000-0002-9776-2794
Russian Federation, Favorsky St., 1, Irkutsk, 664033

I. A. Dorofeev

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

Email: klyba@irioch.irk.ru
ORCID iD: 0000-0003-4646-6554
Russian Federation, Favorsky St., 1, Irkutsk, 664033

V. A. Shagun

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

Email: klyba@irioch.irk.ru
ORCID iD: 0000-0002-2189-7043
Russian Federation, Favorsky St., 1, Irkutsk, 664033

G. A. Fedorova

Limnological Institute, Siberian Branch of the Russian Academy of Sciences

Email: klyba@irioch.irk.ru
ORCID iD: 0000-0002-1697-8631
Russian Federation, Ulan-Batorskaya St, 3, Irkutsk, 664033

References

  1. Никитина П.А., Перевалов В.П. ХГС. 2017, 53, 123–149. [Nikitina P. A., Perevalov V. P., Chem. Heterocycl. Compd. 2017, 53, 123–149.] doi: 10.1007/s10593-017-2030-z.
  2. Iqbal M.A., Haque R.A., Ahamed M.B.K., Maj- id A.M.S., Al-Rawi S.S. Med. Chem. Res. 2013, 22, 2455–2466. doi: 10.1007/s00044-012-0240-6.
  3. Lal A.K., Milton M.D., Tetrahedron Lett. 2014, 55, 1810–1814. doi: 10.1016/j.tetlet.2014.01.127
  4. Аверин К.М., Солодунов Ю.Ю., Страдомский Б.В. Евр. Пат. 013691 В1 2009. Б. И. 2010, 3.
  5. Stradomsky B.V., Solodunov Yu.Yu. Experimental and clinical pharmacology of ointment forms of Stellanin (1,3-diethylbenzimidazolium triiodide), SSC RAS: Rostov-Don, 2013, 89
  6. Сиваев И.Б. ХГС. 2017, 53, 638–658. [Sivaev I.B., Chem. Heterocycl. Compd. 2017, 53, 638–658.] doi: 10.1007/s10593-017-2106-9
  7. Zhang Y., Gao H., Joo Y.-H., Shreeve J. M. Angew. Chem., Int. Ed. 2011, 50, 9554–9562. doi: 10.1002/anie.201101954
  8. Jiang T., Ma X., Zhou Y., Liang S., Zhang J., Han B. Green Chem. 2008, 10, 465–469. doi: 10.1039/B717868A
  9. Headley A.D., Ni B. Aldrichima Acta. 2007, 40, 107–117.
  10. Ishida Y., Sasaki D., Miyauchi H., Saigo K. Tetrahedron Lett. 2006, 47, 7973–7996. doi: 10.1016/j.tetlet.2006.08.101
  11. Iwamoto K., Kimura H., Oike M., Sato M. Org. Biomol. Chem. 2008, 6, 912–915. doi: 10.1039/B719430G
  12. Lee J. P., Yoo B., Suresh T., Kang M. S., Vital R., Kim K. J. Electrochim. Acta. 2009, 54 (18), 4365–4670. doi: 10.1016/j.electacta.2009.03.006
  13. Астахов А.М., Антишин Д.В., Ревенко В.А., Васильев А.Д. Бука Е.С. ХГС. 2017, 53, 722–727. [Astakhov A.M., Antishin D.V., Revenko V.A., Vasil’ev A.D., Buka E S. Chem. Heterocycl. Compd. 2017, 53, 722–727.] doi: 10.1007/s10593-017-2116-7
  14. Kulikov D.V., Karasik A.A., Balueva A.S., Kataeva O.N., Livinov I.A., Hey-Hawkins E., Sinyashin O.G. Mendeleev Commun. 2007, 17, 195–196. doi: 10.1016/j.mencom.2007.06.001
  15. You J.-S., Yu X.-Q., Zhang G.-L., Xiang Q.-X., Lan J.-B., You J.-S., Xie R.-G. Chem. Commun. 2001, 1816–1817. doi: 10.1039/B103325P
  16. Rajakumar P., Dhanasekaran M. Tetrahedron. 2002, 58, 1355–1359. doi: 10.1016/S0040-4020(01)01226-1
  17. Yuan Y., Gao G., Jiang Z.-L., You J.-S., Zhou Z.-Y., Yuan D.-Q., Xie R.-G. Tetrahedron. 2002, 58, 8993–8999. doi: 10.1016/S0040-4020(02)01153-5
  18. Vickers M. S., Beer P. D. Chem. Soc. Rev. 2007, 36, 211–225. doi: 10.1039/B518077P
  19. Yoon J., Kim S.K., Sing N.J., Kim K.S. Chem. Soc. Rev. 2006, 35, 355–360. doi: 10.1039/B513733K
  20. Alcalde E., Alvarez-Rua C., Garcia-Granda S., Garcia- Rodriguez E., Mesquida N., Perez-Garcia L. J. Chem. Soc., Chem. Commun. 1999, 295–296. doi: 10.1039/A808503J
  21. Ярош Н.О., Жилицкая Л.В., Шагун Л.Г., Дорофеев И.А., Ларина Л.И., Воронков М.Г. ЖОрХ. 2013, 49, 486–488. [Yarosh N.O., Zhilitskaya L.V., Shagun L.G., Dorofeev I.A., Larina L.I., Voronkov M.G. Russ. J. Org. Chem. 2013, 49, 475–477.] doi: 10.1134/S1070428013030287
  22. Шагун Л.Г., Дорофеев И.А., Ярош Н.О., Жилицкая Л.В., Ларина Л.И., Воронков М.Г. ЖОрХ. 2013, 49, 1693–1696. [Shagun L.G., Dorofeev I.A., Yarosh N.O., Zhilitskaya L.V., Larina L.I., Voronkov M.G. Russ. J. Org. Chem. 2013, 49 (11), 1676–1679.] doi: 10.1134/S1070428013110195
  23. Воронков М.Г., Шагун Л.Г., Дорофеев И.А., Жилицкая Л.В., Ярош Н.О., Ларина Л.И., Изв. АН. Сер. хим. 2013, 62, 2554–2555. [Voronkov M.G., Shagun L.G., Dorofeev I.A., Zhilitskaya L.V., Yarosh N.O., Larina L.I., Russ. Chem. Bull. Int. Edit. 2013, 62 (11), 2554–2555] doi: 10.1007/s11172-013-0371-z
  24. Ярош Н.О., Жилицкая Л.В., Шагун Л.Г., Дорофеев И.А., Клыба Л.В., Воронков М.Г. ЖОрХ. 2013, 49, 1567–1568. [Yarosh N.O., Zhilitskaya L.V., Shagun L.G., Dorofeev I.A., Klyba L.V., Voronkov M.G. Russ. J. Org. Chem. 2013, 49 (10), 1546–1547.] doi: 10.1134/S1070428013100230
  25. Lobodin V.V., Lebedev A.T., Mass Spectrom. 2005, 2 (2), 91−128
  26. Клыба Л.В., Санжеева Е.Р., Шагун Л.Г., Жилицкая Л.В. ЖОрХ. 2017, 53, 1217–1222. [Klyba L.V., Sanzheeva E.R., Shagun L.G., Zhilitskaya L.V., Russ. J. Org. Chem. 2017, 53 (8), 1233–1238.] doi: 10.1134/S1070428017080127
  27. Клыба Л.В., Санжеева Е.Р., Шагун Л.Г., Жилицкая Л.В. ЖОрХ. 2018, 54, 1369–1343. [Klyba L.V., Sanzheeva E.R., Shagun L.G., Zhilitskaya L.V., Russ. J. Org. Chem. 2018, 54 (9), 1383–1388]. doi: 10.1134/S1070428018090191
  28. Клыба Л.В., Санжеева Е.Р., Шагун Л.Г., Жилицкая Л.В. ЖОрХ. 2020, 56, 88–96. [Klyba L.V., Sanzheeva E.R., Shagun L.G., Zhilitskaya L.V., Russ. J. Org. Chem., 2020, 56 (1), 68–75.] doi: 10.1134/S1070428020010121
  29. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Scalmani G., Barone V., Mennucci B., Petersson G.A., Nakatsuji H., Caricato M., Li X., Hratchian H.P., Izmaylov A.F., Bloino J., Zheng G., Sonnenberg J.L., Hada M., Ehara M., Toyo-ta K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J.A. Jr., Peralta J.E., Ogliaro F., Bearpark M., Heyd J.J., Brothers E., Kudin K.N., Staroverov V.N., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J.C., Iyengar S.S., Tomasi J., Cossi M., Rega N., Millam J.M., Klene M., Knox J.E., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J.W., Martin R.L., Morokuma K., Zakrzewski V.G., Voth G.A., Salvador P., Dannenberg J.J., Dapprich S., Daniels A.D., Farkas O., Foresman J.B., Ortiz J.V., Cioslowski J., and Fox D.J., Gaussian 09, revision A.01,Gaussian, Inc., Wallingford, 2009
  30. Becke A.D., J. Chem. Phys. 1993, 98 (7), 5648–5652. doi: 10.1063/1.464913
  31. Peng C., Ayala P.Y., Schlegal H.B., Frisch M.J. J. Comp. Chem. 1996, 17, 49–56. doi: 10.1002/(SICI)1096-987X(19960115)17:1<49::AID-JCC5>3.0.CO;2-0

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