N-arylation of 1,2,4- and 1,3,4-oxadiazolones under the conditions of activitated aromatic nucleophilic substitution
- Autores: Konstantinova A.S1,2, Shetnev A.A1, Volobueva A.S3, Korsakov M.K2
- 
							Afiliações: 
							- Pharmaceutical Technology Transfer Center, Ushinsky Yaroslavl State Pedagogical University
- Russian State University named after A.N. Kosygin (Technology. Design. Art)
- Saint Petersburg Pasteur Institute
 
- Edição: Volume 59, Nº 11 (2023)
- Páginas: 1435-1445
- Seção: Articles
- URL: https://rjeid.com/0514-7492/article/view/667136
- DOI: https://doi.org/10.31857/S0514749223110058
- EDN: https://elibrary.ru/OGQVBA
- ID: 667136
Citar
Texto integral
 Acesso aberto
		                                Acesso aberto Acesso está concedido
						Acesso está concedido Acesso é pago ou somente para assinantes
		                                							Acesso é pago ou somente para assinantes
		                                					Resumo
The possibilities of N -arylation of 1,2,4-oxadiazol-5(4 Н )-ones and 1,3,4-oxadiazol-2(3 Н )-ones with various electron-deficient chloro- and fluorine-substituted nitroarenes under the conditions of classical activated nucleophilic substitution were studied. A significant difference was shown in the reactivity of 1,2,4- and 1,3,4-oxadiazolones in N -arylation reactions. Methods for the synthesis of N-nitroaryl derivatives have been developed.1,2,4- and 1,3,4-oxadiazolones, providing yields of target products with sufficient purity and good yields at the level of 65-96%.
			                Sobre autores
A. Konstantinova
Pharmaceutical Technology Transfer Center, Ushinsky Yaroslavl State Pedagogical University;Russian State University named after A.N. Kosygin (Technology. Design. Art)
														Email: a.konstantinova@yspu.org
				                					                																			                												                														
A. Shetnev
Pharmaceutical Technology Transfer Center, Ushinsky Yaroslavl State Pedagogical University
														Email: a.shetnev@list.ru
				                					                																			                												                														
A. Volobueva
Saint Petersburg Pasteur Institute
M. Korsakov
Russian State University named after A.N. Kosygin (Technology. Design. Art)
Bibliografia
- Moser P.C., Bergis O.E., Jegham S., Lochead A., Duconseille E., Terranova J.P., Caille D., Berque-Bestel I., Lezoualc H.F., Fischmeister R., Dumuis A., Bockaert J., George P., Soubri� P., Scatton B. J. Pharmacol. Exp. Ther. 2002, 302, 731-741. doi: 10.1124/jpet.102.034249
- Shah S.K., He S., Guo L., Truong Q., Qi H., Du W., Lai Z., Liu J., Jian T., Hong Q., Dobbelaar P., Ye Z., Sherer E., Feng Z., Yu Y., Wong F., Samuel K., Madiera M., Karanam B.V., Reddy V.B., Mitelman S., Tong S.X., Chicchi G.G., Tsao K.L., Trusca D., Feng Y., Wu M., Shao Q., Trujillo M.E., Eiermann G.J., Li C., Pachanski M., Fernandez G., Nelson D., Bunting P., Morissette P., Volksdorf S., Kerr J., Zhang B.B., Howard A.D., Zhou Y.P., Pasternak A., Nargund R.P., Hagmann W. K. ACS Med. Chem. Lett. 2015, 6, 513-517. doi: 10.1021/ml500514w
- Baker W.L., White W.B. Ann. Pharmacother. 2011, 45, 1506-1515. doi: 10.1345/aph.1Q468
- Haffar O., Dubrovsky L., Lowe R., Berro R., Kashanchi F., Godden J., Vanpouille C., Bajorath J., Bukrinsky M. J. Virol. 2005, 79, 13028-13036. doi: 10.1128/JVI.79.20.13028-13036.2005.
- Ohmoto K., Okuma M., Yamamoto T., Kijima H., Sekioka T., Kitagawa K., Yamamoto S., Tanaka K., Kawabata K., Sakata A., Imawaka H., Nakai H., Toda M. Bioorg. Med. Chem. 2001, 9, 1307-1323. doi: 10.1016/s0968-0896(01)00007-4
- Bi F., Song D., Qin Y., Liu X., Teng Y., Zhang N., Zhang P., Zhang N., Ma S. Bioorg. Med. Chem. 2019, 27, 3179-3193. doi: 10.1016/j.bmc.2019.06.010
- Marvadi S.K., Krishna V.S., Sinegubova E.O., Volobueva A.S., Esaulkova Y.L., Muryleva A.A., Tentler D.G., Sriram D., Zarubaev V.V., Kantevari S. Bioorg. Med. Chem. Lett. 2019, 29, 2664-2669. doi: 10.1016/j.bmcl.2019.07.040
- Yue E.W., Sparks R., Polam P., Modi D., Douty B., Wayland B., Glass B., Takvorian A., Glenn J., Zhu W., Bower M., Liu X., Leffet L., Wang Q., Bowman K.J., Hansbury M.J., Wei M., Li Y., Wynn R., Burn T.C., Koblish H.K., Fridman J.S., Emm T., Scherle P.A., Metcalf B., Combs A.P. ACS Med. Chem. Lett. 2017, 8, 486-491. doi: 10.1021/acsmedchemlett.6b00391
- Phakhodee W., Duangkamol C., Wiriya N., Pattarawarapan M. RSC Adv. 2018, 8, 38281-38288. doi: 10.1039/C8RA08207C
- Zhou L., Li H., Zhang W., Wang L. Chem. Commun. 2018, 54, 4822-4825. doi: 10.1039/C8CC00124C
- Sauer J., Mayer K.K. Tetrahedron Lett. 1968, 9, 325-330. doi: 10.1016/s0040-4039(01)98754-4
- Soldatova N., Semenov A., Geyl K., Baykov S., Shetnev A., Konstantinova A., Korsakov M., Yusubov M., Postnikov P. Adv. Synth. Catal. 2021, 363, 1-12. doi: 10.1002/adsc.202100426
- Baykov S., Sharonova T., Shetnev A., Rozhkov S., Kalinin S., Smirnov A. Tetrahedron. 2017, 73, 945-951. doi: 10.1016/j.tet.2017.01.007
- Musser J.H., Brown R.E., Love B., Bailey K., Jones H., Kahen, R., Huang F., Khandwala A., Leibowitz M., Sonnino-Goldman P., Donigi-Ruzza D. J. Med. Chem. 1984, 27, 121-125. doi: 10.1021/jm00368a004
- Van der Linden L., Vives-Adrian L., Selisko B., Ferrer-Orta C., Liu X., Lanke K., Ulferts R., De Palma A.M., Tanchis F., Goris N., Lefebvre D., De Clercq K., Leyssen P., Lacroix C., Purstinger G., Coutard B., Canard B., Boehr D.D., Arnold J.J.,Cameron C.E., Verdaguer N., Neyts J., van Kuppeveld F.J. PLoS Pathog. 2015, 11, 1-23. doi: 10.1371/journal.ppat.1004733
- Hughes G., Bryce M.R. J. Mater. Chem. 2005, 15, 94-107. doi: 10.1039/B413249C
Arquivos suplementares
 
				
			 
						 
						 
					 
						 
						 
									

 
  
  
  Enviar artigo por via de e-mail
			Enviar artigo por via de e-mail 
