Abstract:
1,8-Bis(dimethylamino)naphthalenes bearing 2-positioned trifluoroacetyl or ethoxycarbonyl group on treatment with 2-lithio-1,8-bis-dimethylamino)naphthalene undergo base-promoted transformation into benzo[g]indole derivatives in small to moderate yield, representing previously unknown mode of the pyrrole ring closure which proceeds via deprotonation of the NMe group.
Citation:
S. G. Kachalkina, G. S. Borodkin, A. F. Pozharskii, A. S. Antonov, I. G. Borodkina, Yu. F. Maltsev, E. A. Filatova, A. Filarowski, V. A. Ozeryanskii, “Base-promoted transformation of 2-C(O)R-1,8-bis(dimethylamino)naphthalenes into benzo[g]indole derivatives”, Mendeleev Commun., 25:3 (2015), 182–184
Linking options:
https://www.mathnet.ru/eng/mendc2343
https://www.mathnet.ru/eng/mendc/v25/i3/p182
This publication is cited in the following 7 articles:
Semyon V. Tsybulin, Mark V. Kaplanskiy, Alexander S. Antonov, “Transition‐Metal‐Free Synthesis of 2‐Substituted Benzo[cd]Indoles via the Reaction of 1‐Halo‐8‐lithionaphthalenes with Nitriles”, Chemistry A European J, 30:10 (2024)
Alexander S. Antonov, Elena Yu Tupikina, Valerii V. Karpov, Valeriia V. Mulloyarova, Victor G. Bardakov, “Sterically Facilitated Intramolecular Nucleophilic NMe2 Group Substitution in the Synthesis of Fused Isoxazoles: Theoretical Study”, Molecules, 25:24 (2020), 5977
Alexander F. Pozharskii, Valery A. Ozeryanskii, Ekaterina A. Filatova, Olga V. Dyablo, Olga G. Pogosova, Gennady S. Borodkin, Aleksander Filarowski, Dmitriy V. Steglenko, “Neutral Pyrrole Nitrogen Atom as a π- and Mixed n,π-Donor in Hydrogen Bonding”, J. Org. Chem., 84:2 (2019), 726
Alexander S. Antonov, Victor G. Bardakov, Alexander F. Pozharskii, Mikhail A. Vovk, Alexander D. Misharev, “Laying the way to meta -functionalization of naphthalene proton sponge via the use of Schlosser's superbase”, Journal of Organometallic Chemistry, 855 (2018), 18
Alexander S. Antonov, Svetlana G. Kachalkina, Alexander F. Pozharskii, Gennady S. Borodkin, Aleksander Filarowski, “Reaction of 2-trifluoroacetyl-1,8-Bis(dimethylamino)naphthalene with strong organic bases: Deprotonation of 1-NMe2 group resulting in the formation of Benzo[g]indole derivatives versus nucleophilic addition to C O group”, Tetrahedron, 73:25 (2017), 3452
Svetlana G. Kachalkina, Gennady S. Borodkin, Alexander F. Pozharskii, Alexander S. Antonov, Inna G. Borodkina, Yuri F. Maltsev, Ekaterina A. Filatova, Aleksander Filarowski, Valery A. Ozeryanskii, “ChemInform Abstract: Base‐Promoted Transformation of 2‐C(O)R‐1,8‐Bis(dimethylamino)naphthalenes into Benzo[g]indole Derivatives.”, ChemInform, 46:41 (2015)
Alexander S. Antonov, Alexander F. Pozharskii, Valery A. Ozeryanskii, Aleksander Filarowski, Kyrill Yu. Suponitsky, Peter M. Tolstoy, Mikhail A. Vovk, “Ring lithiation of 1,8-bis(dimethylamino)naphthalene: another side of the 'proton sponge coin'”, Dalton Trans., 44:40 (2015), 17756
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