Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 2, Pages 278-283Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201701451
Keywords
multicomponent reactions; nitrogen heterocycles; one-pot reaction; quinolines; tetrahydroquinolines
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Funding
- Basic Science Research Program and Nano.Material Technology Department Program through the National Research Foundation of Korea (NRF) - Korea government (MSIP) [2012 M3A7B4049644, 2014-011165, 2015R1A2A2A01002559]
- National Research Foundation of Korea [2015R1A2A2A01002559] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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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.
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