Oxidative triflamidation of allyl cyanide in nitrile solutions
- Autores: Ganin A.S.1, Sobyanina M.M.1, Moskalik M.Y.1, Shainyan B.A.1
- 
							Afiliações: 
							- A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
 
- Edição: Volume 59, Nº 11 (2023)
- Páginas: 1410-1417
- Seção: Articles
- URL: https://ruspoj.com/0514-7492/article/view/667132
- DOI: https://doi.org/10.31857/S0514749223110022
- EDN: https://elibrary.ru/NHKGIG
- ID: 667132
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 reaction of triflamide with allyl cyanide in benzonitrile and isobutyronitrile solutions in the presence of NBS has been studied. In both cases, the corresponding amidines - the products of the solvent incorporation are formed. In benzonitrile, depending on the reaction conditions, the isomeric N -(2-bromo-3-cyanopropyl)- N '-(triflyl)benzamidine and N -(1-bromo-3-cyanoprop-2-yl)- N '-(triflyl)benzamidine were obtained in various ratio. From the reaction in isobutyronitrile, N -(2-bromo-3-cyanopropyl)- N '-(triflyl)isobutyramidine and the product of diamination, N -[3-cyano-1-(triflamido)propyl]isobutyramide were isolated.
			                Palavras-chave
Sobre autores
A. Ganin
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
														Email: ganin@irioch.irk.ru
				                					                																			                												                														
M. Sobyanina
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
M. Moskalik
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
B. Shainyan
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
Bibliografia
- Minakata S., Morino Y., Oderaotoshi Y., Komatsu M. Org. Lett. 2006, 8, 3335-3337. doi: 10.1021/ol061182q
- Gao P., Wei Y. Heterocycl. Commun. 2013, 19, 113-119. doi: 10.1515/hc-2012-0179
- Minakata S., Morino Y., Oderaotoshi Y., Komatsu M. Chem. Commun. 2006, 31, 3337-3339. doi: 10.1039/B606499J
- Yang H.-T., Ren W.-L., Dong C.-P., Yang Y., Sun X.-Q., Miao C.-B. Tetrahedron Lett. 2013, 54, 6799-6803. doi: 10.1016/j.tetlet.2013.09.002
- Fan R., Pu D., Gan J., Wang B. Tetrahedron Lett. 2008, 49, 4925-4928. doi: 10.1016/j.tetlet.2008.05.143
- Suzuki S., Saito A. J. Org. Chem. 2017, 82, 11859-11864. doi: 10.1021/acs.joc.7b01563
- Inturi S.B., Kalita B., Ahamed A.J. Org. Biomol. Chem. 2016, 14, 11061-11064. doi: 10.1039/C6OB01926A
- Kiyokawa K., Kosaka T., Minakata S. Org. Lett. 2013, 15, 4858-4861. doi: 10.1021/ol402276f
- Yoshimura A., Nemykin V.N., Zhdankin V.V. Chem. Eur. J. 2011, 17, 10538-10541. doi: 10.1002/chem.201102265
- Kobayashi Y., Masakado S., Takemoto Y. Angew. Chem. Int. Ed. 2018, 57, 693-697. doi: 10.1002/anie.201710277
- Conry R.R., Tipton A. A., Striejewske W.S., Erkizia E., Malwitz M.A., Caffaratti A., Natkin J.A. Organometallics. 2004, 23, 5210-5218. doi: 10.1021/om040098g
- Gopalan G., Dhanya B.P., Saranya J., Reshmitha T.R., Baiju T.V., Meenu M.T., Nair M.S., Nisha P., Radhakrishnan K.V. Eur. J. Org. Chem. 2017, 3072-3077. doi: 10.1002/ejoc.201700410
- Wu X.-L., Xia J.-J., Wang G.-W. Org. Biomol. Chem. 2008, 6, 548-553. doi: 10.1039/B717333D
- Wu X.-L., Wang G.-W. Tetrahedron. 2009, 65, 8802-8807. doi: 10.1016/j.tet.2009.08.069
- Morino Y., Hidaka I., Oderaotoshi Y., Komatsu M., Minakata S. Tetrahedron. 2006, 62, 12247-12251. doi: 10.1016/j.tet.2006.10.003
- Cai Y., Liu X., Li J., Chen W., Wang W., Lin L., Feng X. Chem. Eur. J. 2011, 17, 14916-14921. doi: 10.1002/chem.201102453
- Knight J.G., Muldowney M.P. J. Synlett. 1995, 9, 949-951. doi: 10.1055/s-1995-5128
- Wu Q., Hu J., Ren X., Zhou J. Chem. Eur. J. 2011, 17, 11553-11558. doi: 10.1002/chem.201101630
- Ganin A.S., Moskalik M.Y., Astakhova V.V., Sterkhova I.V., Shainyan B.A. Tetrahedron. 2020, 76, 131374. doi: 10.1016/j.tet.2020.131374
- Ganin A.S., Moskalik M.Y., Garagan I.A., Astakhova V.V., Shainyan B.A. Molecules. 2022, 27, 6910. doi: 10.3390/molecules27206910
- Bouchoux G. Mass Spectrom. Rev. 2018, 37, 533-564. doi: 10.1002/mas.21538
- Moskalik M.Y., Astakhova V.V., Shainyan B.A. RSC Adv. 2020, 10, 40514-40528. doi: 10.1039/d0ra07469a
- 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., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J.A., 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 N.J., 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., Fox D.J. Gaussian 09, revision Е.01, Wallingford: Gaussian Inc., 2009.
Arquivos suplementares
 
				
			 
						 
						 
					 
						 
						 
									

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