Skeletal Modification of Phenols into Benzo-Fused Seven-Membered N,O-Heterocycles via Catalytic Alkyl Nitrene
Prasoon R Singh1, Yasuko Asada1, Hidetoshi Noda1
1Institute of Microbial Chemistry (BIKAKEN), Tokyo 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.
Abstract:
Saturated seven-membered N-heterocycles are underrepresented in drug discovery due to the scarcity of reliable synthetic methods. Herein, we report a rhodium-catalyzed strategy for constructing benzo-fused seven-membered N,O-heterocycles from phenols via intramolecular nitrene C(sp2)-H amination. The reaction is scalable with catalyst loadings as low as 0.1 mol %, enables solvent recovery, and allows for the late-stage annulation of diverse phenolic natural products and drug derivatives.
More Related Videos
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
10:42Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Related Concept Videos
Nucleophilic Aromatic Substitution: Elimination–Addition
Electrophilic Aromatic Substitution: Nitration of Benzene
Benzene to Phenol via Cumene: Hock Process
Reactions at the Benzylic Position: Oxidation and Reduction
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
