89228-37-5Relevant academic research and scientific papers
Metal-Free One-Pot Synthesis of (Tetrahydro)Quinolines through Three-Component Assembly of Arenediazonium Salts, Nitriles, and Styrenes
Youn, So Won,Yoo, Huen Ji,Lee, Eun Mi,Lee, Seo Young
supporting information, p. 278 - 283 (2017/12/26)
A highly efficient and convenient metal-free, one-pot synthesis of diversely substituted (tetrahydro)quinolines has been achieved through a three-component assembly reaction of arenediazonium salts, nitriles, and styrenes. In sharp contrast to the prior works with the same reagent blend, the formation of N-arylnitrilium intermediates from arenediazonium salts and nitriles was followed by reaction with styrenes, leading to 3,4-dihydroquinolinium salts as a common intermediate. These could be further transformed to quinolines and tetrahydroquinolines depending on the reaction conditions. The advantages of this protocol include its simplicity, metal-free and mild conditions, readily available starting materials, and good functional group tolerance. (Figure presented.).
THE PALLADIUM-CATALYSED CONJUGATE ADDITION TYPE REACTION OF 2-(N-ACYLAMINO)-ARYLMERCURY COMPOUNDS WITH α,β-ENONES: A NEW ENTRY TO THE QUINOLINE SKELETON
Cacchi, S.,Palmieri, G.
, p. 3373 - 3384 (2007/10/02)
Pd-catalysed reaction of arylmercurials with α,β-enones in an acidic two-phase system gives conjugate addition products useful for the synthesis of quinolines, 3,4-dihydroquinolines, and 1,2,3,4-tetrahydroquinolines.
