Potassiumtert‐Butoxide‐Mediated Synthesis of 2‐Aminoquinolines from Alkylnitriles and 2‐Aminobenzaldehyde Derivatives

Abstract

KOtBu mediates the reaction between 2‐amino arylcarbaldehydes and benzyl/alkyl cyanides toward the expeditious formation of 2‐aminoquinolines under transition‐metal‐free conditions. The described transformation proceeds through in‐situ generated enimine intermediate from benzyl/alkyl cyanides under KOtBu‐mediated reaction conditions. The substituted 2‐aminoquinolines were realized in excellent yields at room temperature and shorter reaction time. The designed process exhibits operational simplicity and broad functional group tolerance in delivering the products of high significance.

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

“…Quinoline is a privileged fused heterocycle, commonly present in natural products [50–52] . Over the years, various efficient synthetic routes for synthesizing quinoline derivatives have been developed [53–55] . Biaryl compounds like developments of biquinoline synthesis by transforming heterocyclic N ‐oxides directly into N ‐heterobiaryls and transition‐metal‐catalyzed cross‐coupling reactions are quite well‐known.…”

“…[50][51][52] Over the years, various efficient synthetic routes for synthesizing quinoline derivatives have been developed. [53][54][55] Biaryl compounds like developments of biquinoline synthesis by transforming heterocyclic N-oxides directly into N-heterobiaryls and transition-metal-catalyzed cross-coupling reactions are quite well-known. The Cu-catalyzed tandem aerobic oxidative cyclization reaction (Scheme 4 (a)) and I 2 /peroxide-catalyzed oxidative dehydrogenation tandem cyclization reaction (Scheme 4 (b)) have been reported as effective methods.…”