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Regioselective Synthesis of 1,2‐ and 1,4‐Dihydroquinolines by Palladium‐Catalyzed Intramolecular N‐Arylation
Author(s) -
Park KyeongYong,
Lee Jinyong,
Park Seong Jun,
Heo JungNyoung,
Lim Hwan Jung
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500627
Subject(s) - chemistry , intramolecular force , regioselectivity , isomerization , palladium , catalysis , double bond , medicinal chemistry , organic chemistry , combinatorial chemistry
A series of 1,2‐ and 1,4‐dihydroquinolines has been successfully prepared. The Pd‐catalyzed intramolecular N‐arylation of Z ‐enamines, formally prepared by the Horner–Wadsworth–Emmons olefination, proceeded efficiently to furnish the cyclized products. Depending on the cyclization conditions, substituted 1,4‐dihydroquinolines and further isomerized 1,2‐dihydroquinolines were independently obtained in high yields with an excellent control of isomerization of the double bond.