Anthony D. Sercel

Simple Synthesis of 4‐Substituted 1(2H)‐Isoquinolinones via Electrophilic Trapping of Lithiated Mono‐ and Dianion Precursors

Abstract Synthetic routes have been developed to access 4‐substituted 1(2H)‐isoquinolinones from readily available precursors. This is achieved via electrophilic trapping of di‐ and monolithium anions derived from alkyllithium exchange of 4‐bromo‐1(2H)‐isoquinolinones and corresponding 4‐bromo‐1‐methoxyisoquinolines, respectively. Products derived from the latter are then hydrolyzed to the target 4‐substituted 1(2H)‐isoquinolinones. The methodology has potential application to access 4‐substituted 1(2H)‐isoquinolinones with additional substituents in either ring.

A simple method for preparation of N-mono- and N,N-di-alkylated α-amino acids

Abstract Reactions of α-amino acids with ketones under hydrogenation conditions using 20% Pd(OH) 2 /C as the catalyst gave N -mono-alkylated amino acids in high yields. Reductive methylation of N -mono-alkylated amino acids under the same hydrogenation conditions at 50°C afforded N , N -di-alkylated amino acids in excellent yields. This simple method has been used to synthesize N -mono- and N , N -di-alkylated amino acids on a scale of 200 g.