Gini, Andrea and Bamberger, Julia and Luis-Barrera, Javier and Zurro, Mercedes and Mas-Balleste, Ruben and Aleman, Jose and Mancheno, Olga Garcia (2016) Synthesis of 3-Benzazepines by Metal-Free Oxidative C-H Bond Functionalization-Ring Expansion Tandem Reaction. ADVANCED SYNTHESIS & CATALYSIS, 358 (24). pp. 4049-4056. ISSN 1615-4150, 1615-4169
Full text not available from this repository. (Request a copy)Abstract
A metal-free synthesis of biologically important benzazepines is achieved through a single synthetic operation involving an oxidative C-H bond functionalization and ring expansion with diazomethanes as key reagent. This represents a new, strong methodology for the straightforward construction of the seven-ring N-heterocyclic structures under mild conditions using a 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) oxoammonium salt as oxidant. Moderate to good yields are achieved from simple, readily available tetrahydroisoquinolines, and this methodology has been further successfully applied for the synthesis of the 3-benzazepine drug Lorcaserin. A possible mechanistic pathway for the ring expansion step, comprising the extrusion of nitrogen in a concerted asynchronic process, is proposed based on both mechanistic proof and density function theory (DFT) calculations.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | FRIEDEL-CRAFTS CYCLIZATION; COUPLING REACTIONS; TERTIARY-AMINES; DIAZO-COMPOUNDS; TETRAHYDROISOQUINOLINES; MILD; TETRAHYDRO-3-BENZAZEPINES; DERIVATIVES; FENOLDOPAM; CYANATION; benzazepines; isoquinolines; metal-free conditions; ring-expansion; tandem reaction |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Olga Garcia Mancheño |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 15 Mar 2019 11:30 |
| Last Modified: | 15 Mar 2019 11:30 |
| URI: | https://pred.uni-regensburg.de/id/eprint/3836 |
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