Tsybulin, Semyon V. and Kaplanskiy, Mark V. and Antonov, Alexander S. (2024) Transition-Metal-Free Synthesis of 2-Substituted Benzo[cd]Indoles via the Reaction of 1-Halo-8-lithionaphthalenes with Nitriles. CHEMISTRY-A EUROPEAN JOURNAL, 30 (10). ISSN 0947-6539, 1521-3765
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A simple and effective organolithium approach to the synthesis of 2-substituted benzo[cd]indoles from peri-dihalonaphthalenes and nitriles has been developed. The reaction proceeds via a surprisingly easy intramolecular aromatic nucleophilic substitution facilitated by the "clothespin effect". The discovered transformation provides good isolated yields, allows usage of an extensive range of nitriles, and demonstrates a good substituents tolerance. UV-absorption and NMR spectra of the obtained benzo[cd]indoles and their protonated forms demonstrated exclusive protonation to the indole nitrogen atom even in the presence of two NMe2 groups in positions 5 and 6 (i. e. "proton sponge" moiety).
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PROTON SPONGE; INHIBITORS; INDOLE; DESIGN; BOND; organolithiums; indoles; heterocycles; nucleophilic substitution; naphthalene |
| Subjects: | 600 Technology > 610 Medical sciences Medicine |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 28 Jul 2025 08:49 |
| Last Modified: | 28 Jul 2025 08:49 |
| URI: | https://pred.uni-regensburg.de/id/eprint/63834 |
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