Oxidative triflamidation of allyl cyanide in nitrile solutions
- 作者: Ganin A.S.1, Sobyanina M.M.1, Moskalik M.Y.1, Shainyan B.A.1
-
隶属关系:
- A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
- 期: 卷 59, 编号 11 (2023)
- 页面: 1410-1417
- 栏目: Articles
- URL: https://journals.eco-vector.com/0514-7492/article/view/667132
- DOI: https://doi.org/10.31857/S0514749223110022
- EDN: https://elibrary.ru/NHKGIG
- ID: 667132
如何引用文章
详细
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.
作者简介
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
参考
- 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.
补充文件
