First examples of phosphoric anhydride mediated O- and N-acylation
- Authors: Shafran Y.M.1, Pospelova T.A.1
- 
							Affiliations: 
							- Chemical-Technological Institute, Ural Federal University
 
- Issue: Vol 93, No 12 (2023)
- Pages: 1807-1821
- Section: Articles
- URL: https://cardiosomatics.ru/0044-460X/article/view/667261
- DOI: https://doi.org/10.31857/S0044460X23120016
- EDN: https://elibrary.ru/NZZIWX
- ID: 667261
Cite item
Abstract
It was shown that phosphoric anhydride can be used for the synthesis of esters and amides of carboxylic acids when they react with compounds containing hydroxyl and primary amino groups. A new method was proposed for obtaining paracetamol. An example of the reverse reactivity of these nucleophilic centers located in para -aminophenol molecule was revealed.
			                About the authors
Yu. M. Shafran
Chemical-Technological Institute, Ural Federal University
														Email: yu.m.shafran@urfu.ru
				                					                																			                												                														
T. A. Pospelova
Chemical-Technological Institute, Ural Federal University
References
- Перечень прекурсоров и необходимых химикатов, которые обычно используются для нелегального производства некоторых подлежащих контролю веществ. https://www.consultant.ru/document/cons_doc_LAW_283828/ce505a5244637b5dbb0cc62b4d7ad0ea121b5aad/?ysclid=llw6ow937l355247465
- Wang Q., Deng Y. Pat. CN102675080A (2014). China.
- Шафран Ю.М., Бакулев В.А., Шевырин В.А., Колобов М.Ю. // ХГС. 1993. № 6. С. 840
- Shafran Yu.M., Bakulev V.A., Shevyrin V.A., Kolobov M.Yu. // Chem. Heterocycl. Compd. 1993. N 11. P. 724. doi: 10.1007/bf00531556
- Beliaev N., Shafran Yu. Pat. WO2016038061Al (2016).
- Micheli R.A., Booth A.N., Livingston A.L., Bickoff E.M. // J. Med. Pharm. Chem. 1962. Vol. 5. P. 321. doi: 10.1021/jm01237a010
- Wessely F., Prillinger F. // Chem. Ber. 1939. Bd 72. S. 629.
- Marrian G.F., Haslewood G.A.D. // Biochem. J. 1932. Vol. 26. P. 1227. doi: 10.1042/bj0261227
- Ohta H., Ishizaka T., Tatsuzuki M., Yoshinaga M., Iida I., Yamaguchi T., Tomishima Y., Futaki N., Toda Y., Saito S. // Bioorg. Med. Chem. 2008. Vol. 16. N 3. P. 1111. doi: 10.1016/j.bmc.2007.10.087
- Chemical Note. https://chemicalnote.com/formic-acid-methanoic-acid-laboratory-preparation-properties-and-uses
- Jones C.D., Luke R.W.A, Mccoull W. Pat. WO2005060970 (2005).
- Medina-Ramos W., Mojica M.A., Cope E.D., Hart R.J., Pollet P., Eckert Ch.A., Liotta Ch.L. // Green Chem. 2014. Vol. 16. N 4. P. 2147. doi: 10.1039/c3gc42569j
- Yamamoto T., Harigaya Y., Okawara M. // Tetrahedron. 1978. Vol. 34. N 20. P. 3097. doi: 10.1016/0040-4020(78)87005-7
- Wang Y., Liu W.-J., Yin L., Li H., Chen Z.-H., Zhu D.-X., Song X.-Q., Cheng Z.-Z., Song P., Wang Z., Li Z.-G. // Bioorg. Med. Chem. Let. 2018. Vol. 28. N 5. P. 974. doi: 10.1016/j.bmcl.2017.12.068
- Kalyvas V., McIntyre J.E. // Mol. Cryst. Liq. Cryst. 1982. Vol. 80. N. 1. P. 105. doi: 10.1080/00268948208071024
- El-Gamal M.I., Zaraei S.O., Foster P.A., Anbar H.S., El-Gamal R., El-Awady R., Potter B.V.L. // Bioorg. Med. Chem. 2020. Vol. 28. N 8. P. 115406. doi: 10.1016/j.bmc.2020.115406.
- Sovak M., Terry R.C., Douglass J.G., Bakir F., Brown J., Cugley P. Pat. WO2001008647 (2001).
- Bhardwaj B., Nivrutti A.A., Saraf P., Shrivastava S.K., Tripathi M., Tripathi P.N., Verma A., Waiker D.K. // J. Mol. Struct. 2022. Vol. 1262. doi: 10.1016/j.molstruc.2023.135517
- Xu T., Alper H. // J. Am. Chem. Soc. 2014. Vol. 136. N 49. P. 16970. doi: 10.1021/ja508588b
- Ikeda S.-I., Kimura U., Ashizawa T., Gomi K., Saito H., Kasai M., Kanazawa J., Sasaki K., Nukui E., Okabe M., Sato S. Pat. US 5952355A (1999). USA.
- Línzembold I., Czett D., Böddi K., Kurtán T., Király S.B., Gulyás-Fekete G., Takátsy A., Lóránd T., Deli J., Agócs A., Nagy V. // Molecules. 2020. Vol. 25. N 3. P. 636. doi: 10.3390/molecules25030636
- Sowjanya T., Jayaprakash Rao Y., Murthy N.Y.S. // Russ. J. Gen. Chem. 2017. Vol. 87. N 8. P. 1864. doi: 10.1134/s1070363217080357
- Majumdar S., Sloan K.B. // Int. J. Pharm. 2007. Vol. 337. N. 1-2. P. 48. doi: 10.1016/j.ijpharm.2006.12.026
- Horner L., Steppan H. // Ann. 1957. Vol. 606. P. 24.
- Itoh N., Sakamoto T., Miyazawa E., Kikugawa Y. // J. Org. Chem. 2002. Vol. 67. N 21. P. 7424. doi: 10.1021/jo0260847
- Vickers S., Triggle D.J., Garrison D.R. // J. Chem. Soc. (C). 1968. P. 632. doi: 10.1039/J39680000632
Supplementary files
 
				
			 
					 
						 
						 
						 
						 
									

 
  
  
  Email this article
			Email this article 
 Open Access
		                                Open Access Access granted
						Access granted Subscription or Fee Access
		                                							Subscription or Fee Access
		                                					