Visible-Light-Mediated Oxidative Cyclization of 2-Aminobenzyl Alcohols and Secondary Alcohols Enabled by an Organic Photocatalyst

Abstract

This paper describes a visible-light-mediated oxidative cyclization of 2-aminobenzyl alcohols and secondary alcohols to produce quinolines at room temperature. This photocatalytic method employed anthraquinone as an organic small-molecule catalyst and DMSO as an oxidant. According to this present procedure, a series of quinolines were prepared in satisfactory yields.

Bioinspired o-Naphthoquinone-Catalyzed Aerobic Oxidation of Alcohols to Aldehydes and Ketones

“… Thus, the in situ generated aldehydes from the o -NQ-catalyzed aerobic oxidation were treated with α-cyano arylsulfonyl compounds to give the corresponding 2-amino-3-sulfonyl quinolines 3a – 3k in good to excellent yields of 49–91%. In addition, the concomitant oxidation of 2-aminobenzyl alcohols and 1-phenylethanol 1x allowed the preparation of substituted quinolines 3l – 3s under basic conditions in 53–96% yields in a one-pot fashion …”

Deaminative Cyclization of Tertiary Amines for the Synthesis of 2-Arylquinoline Derivatives with a Nonsubstituted Vinylene Fragment

“…As is well-known, alkyl quinolines usually show greater activity in pharmaceuticals, agrochemicals, and functional materials because an alkyl chain is capable of enhancing the overall lipophilicity . Despite their tremendous applications, access to alkyl-substituted quinolines at the β-position is commonly difficult by direct alkylation or traditional methods . Significantly, this created deaminative cyclization reaction of triethylamine was successfully extended to other long-chain tertiary alkylamines for assembling another class of 2-alkyl-3-arylbenzo­[ f ]­quinolines, which provided an exciting platform to acquire a high yield of alkyl quinoline derivatives (Scheme ).…”

Schiff‐base Polymer Immobilized Ruthenium for Efficient Catalytic Cross‐coupling of Secondary Alcohols with 2‐amino‐ and γ‐aminobenzyl Alcohols to Give Quinolines and Pyridines

“…The authors have cited additional references within the Supporting Information. [33][34][35][36][37][38][39][40][41][42][43][44][45]…”

“…1 H & 13 C NMR of coupling products are provided in Figures S8–S36. The authors have cited additional references within the Supporting Information [33–45] …”