Direct C-phosphorylation of 1-aryl- and 1-hetarylimidazoles by chlorides of phosphonic acids

Authors

  • A. V. Strizhak Taras Shevchenko National University of Kiev
  • I. V. Komarov Taras Shevchenko National University of Kiev
  • M.Yu. Kornilov Taras Shevchenko National University of Kiev
  • V.P. Khilya Taras Shevchenko National University of Kiev

DOI:

https://doi.org/10.15407/dopovidi2016.02.087

Keywords:

benzoimidazole, imidazole, phosphinamide, phosphinic acid, phosphorylation

Abstract

A convenient efficient method for the synthesis of 1-aryl- and 1-hetarylimidazole and benzoimidazole-2-ylphosphinic acids and their derivates has been proposed. Influence of a group at position 1 of imidazole on its reactivity towards phosphonic acids chlorides is investigated. It is shown that this method provides derivates with different substituents at an aryl or hetaryl ring. This method is a good alternative to the known methods of synthesis of such compounds.

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References

Kunz P. C., Kassack M. U., Hamacher A., Spingler B. Dalton Trans., 2009, 37: 7741–7747. https://doi.org/10.1039/b902748c

Wetzel C., Kunz P. C., Kassack M. U., Hamacher A., Böhler P., Watjen W., Ott I., Rubbianid R., Spinglerer B. Dalton Trans., 2019, 40: 9212–9220.

Honjo M., Maruyama T., Horikawa M., Balzarini J., de Clercq E. Chem. Pharm. Bull., 1987, 35, No 8: 3227–3234. https://doi.org/10.1248/cpb.35.3227

Dang Q., Brown B. S., Liu Y., Rydzewski R. M., Robinson E. D., van Poelje P. D., Reddy M. R., Erion M. D. J. Med. Chem., 2009, 52: 2880–2898. https://doi.org/10.1021/jm900078f

Schulz T., Torborg C., Schöffner B., Huang J., Zapf A., Kadyrov R., Borner A., Beller M. Angew. Chem. Int. Ed., 2009, 48: 918–921. https://doi.org/10.1002/anie.200804898

Antognazzaa P., Benincoria T., Mazzoli S., Sannicoloa F., Pilati T. Phosphorus, Sulfur, and Silicon, 1999, 144: 405–408. https://doi.org/10.1080/10426509908546267

Curtis N. J., Brown R. S. J. Org. Chem., 1980, 45: 4038–4040. https://doi.org/10.1021/jo01308a019

Pinchuk A. M., Tolmachev A. A., Kostyuk A. N., Yurchenko A. A., Sviridon A. I. Phosphorus, Sulfur, Silicon, 1996, 109: 477–480. https://doi.org/10.1080/10426509608545194

Komarov I. V., Kornilov M.Yu., Turov A. V., Gorichko M. V., Popov V. O., Tolmachev A. A., Kirby A. J. Tetrahedron, 1995, 51, No 45: 12417–12424. https://doi.org/10.1016/0040-4020(95)00797-C

Komarov I. V., Strizhak A. V., Kornilov M.Yu., Kostyuk A. N., Tolmachev A. A. Synthetic Communications, 1998, 28, Iss. 13: 2355–2370. https://doi.org/10.1080/00397919808004288

Lv X., Bao W. J. Org. Chem., 2007, 72, No 10: 3863–3867. https://doi.org/10.1021/jo070443m

Zhang Q„ Luo J., Wei Y. Synthetic Communications, 2012, 42, Iss. 1: 114–121. https://doi.org/10.1080/00397911.2010.523149

Zhu L., Cheng L., Zhang Y., Xie R., You J. J. Org. Chem., 2007, 72, Iss. 8: 2737–2743. https://doi.org/10.1021/jo062059f

Xi Zh., Liu F., Zhou Y., Chen W. Tetrahedron, 2008, 64: 4254–4259. https://doi.org/10.1016/j.tet.2008.02.082

Steiner G., Gries J., Lenke D. J. Med. Chem., 1981, 24, No 1: 59–63. https://doi.org/10.1021/jm00133a013

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Published

29.09.2024

How to Cite

Strizhak, A. V., Komarov, I. V., Kornilov, M., & Khilya, V. (2024). Direct C-phosphorylation of 1-aryl- and 1-hetarylimidazoles by chlorides of phosphonic acids . Reports of the National Academy of Sciences of Ukraine, (2), 87–95. https://doi.org/10.15407/dopovidi2016.02.087

Issue

No. 2 (2016): Reports of the National Academy of Sciences of Ukraine

Section

Chemistry

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