A novel synthesis of substituted quinolines using ring-closing metathesis (RCM): its application to the synthesis of key intermediates for anti-malarial agents

Synthesis of quinolines by ruthenium-catalyzed heteroannulation of anilines with 3-amino-1-propanol

Preparation of nitrogen-containing heterocycles using ring-closing metathesis (RCM) and its application to natural product synthesis

Since its original discovery over a century ago, the water-gas shift reaction (WGSR) has played a crucial role in industrial chemistry, providing a source of H2 to feed fundamental industrial transformations such as the Haber–Bosch synthesis of ammonia. Although the production of hydrogen remains nowadays the major application of the WGSR, the advent of homogeneous catalysis in the 1970s marked the beginning of a synergy between WGSR and organic chemistry. Thus, the reducing power provided by the CO/H2O couple has been exploited in the synthesis of fine chemicals; not only hydrogenation-type reactions, but also catalytic processes that require a reductive step for the turnover of the catalytic cycle. Despite the potential and unique features of the WGSR, its applications in organic synthesis remain largely underdeveloped. The topic will be critically reviewed herein, with the expectation that an increased awareness may stimulate new, creative work in the area.

Harnessing the Power of the Water-Gas Shift Reaction for Organic Synthesis

Metal complex catalysis in the synthesis of quinolines

The catalytic N-alkylation and N-heterocyclization of nitrobenzene occurs at 180°C under pressures of carbon monoxide(70 atm) in the presence of aldehyde and transition metal complexes to give 2,3-dialkyl quinoline and N,N-dialkylaniline in good yields. The product selectivity highly depends on the catalysts.

The transition metal-catalyzed n-alkylation and n-heterocyclization. a reductive transformation of nitrobenzene into n,n-dialkylaniline and 2,3-substituted quinoline using aldehyde and carbon monoxide

Naoki Suzuki

Papers

The transition metal-catalyzed n-alkylation and n-heterocyclization. a reductive transformation of nitrobenzene into n,n-dialkylaniline and 2,3-substituted quinoline using aldehyde and carbon monoxide

The transition metal-catalyzed n-alkylation and n-heterocyclization. a reductive transformation of nitrobenzene into n,n-dialkylaniline and 2,3-substituted quinoline using aldehyde and carbon monoxide