Abstract:
Transformations of THF–1-boraadamantane 1 into 1-(1-hydroxyethyl)adamantane 5 and the hydrochioride salt of 1-(1-aminoethyl)adamantane (rimantadine) 9, based on a series of 1,2-anionotropic rearrangements in the corresponding ‘ate’-complexes, are presented.
Document Type:
Article
Language: English
Citation:
M. E. Gurskii, T. V. Potapova, Yu. N. Bubnov, “Synthesis of Rimantadine from 1-Boraadamantane”, Mendeleev Commun., 3:2 (1993), 56–57
Linking options:
https://www.mathnet.ru/eng/mendc5264
https://www.mathnet.ru/eng/mendc/v3/i2/p56
This publication is cited in the following 11 articles:
Donald S. Matteson, Beatrice S. L. Collins, Varinder K. Aggarwal, Engelbert Ciganek, P. Andrew Evans, Organic Reactions, 2021, 427
Tegan P. Stockdale, Craig M. Williams, “Pharmaceuticals that contain polycyclic hydrocarbon scaffolds”, Chem. Soc. Rev., 44:21 (2015), 7737
Yu.N. Bubnov, M.E. Gurskii, S.Yu. Erdyakov, O.A. Kizas, G.D. Kolomnikova, N.Yu. Kuznetsov, T.V. Potapova, O.A. Varzatskii, Y.Z. Voloshin, “Allylic boranes are chemist's best friends: Reactivity, applications, new opportunities”, Journal of Organometallic Chemistry, 694:11 (2009), 1754
M. E. Gurskii, S. Yu. Erdyakov, T. V. Potapova, Yu. N. Bubnov, “Allylboranes and the synthesis of diamond molecules”, Russ Chem Bull, 57:4 (2008), 802
Kim F. Albizati, Donald S. Matteson, Encyclopedia of Reagents for Organic Synthesis, 2005
Carl E. Wagner, Kenneth J. Shea, “Synthesis and First Molecular Structure of a Bis-2-spiro-1-boraadamantane Derivative”, Org. Lett., 6:3 (2004), 313
Yu. N. Bubnov, M. E. Gurskii, D. G. Pershin, K. A. Lyssenko, M. Yu. Antipin, “Complexes of 1-boraadamantane and its derivatives with 1-azaadamantanes: Synthesis and molecular structure”, Russ Chem Bull, 47:9 (1998), 1771
M. E. Gursky, T. V. Potapova, Yu. N. Bubnov, “2,2′-ethylenedi-1-boraadamantane—a new derivative of 1-boraadamantane”, Russ Chem Bull, 47:4 (1998), 728
Comprehensive Heterocyclic Chemistry II, 1996, 1169
Yuri N. Bubnov, Mikhail E. Gurskii, Ilya D. Gridnev, Comprehensive Heterocyclic Chemistry II, 1996, 889
M. E. GURSKII, T. V. POTAPOVA, YU. N. BUBNOV, “ChemInform Abstract: Synthesis of Rimantadine form 1‐Boraadamantane.”, ChemInform, 25:33 (1994)
Contact us: