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Synthesis of Five‐Membered Ring Heteroaryl Pyridines from Heteroaryllithium and N ‐Ethoxycarbonylpyridinium Chlorides
Author(s) -
Lai LongLi,
Shin LiHua,
Lin PenYuan,
Wang JyShih,
Shiao MinJen
Publication year - 1994
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199400009
Subject(s) - chemistry , regioselectivity , chloride , ring (chemistry) , catalysis , medicinal chemistry , reaction conditions , organic chemistry
Furylpyridines, thienylpyridines, and imidazolylpyridines were obtained regioselectively in 40‐67% yields from the reaction of heteroaryllithiums with N ‐ethoxycarbonylpyridinium chloride or N ‐ethoxycarbonyl‐3‐methylpyridinium chloride in the presence of Cul in a catalytic amount at −78 °C or −50°C, then followed by oxidation. The regioselectivity of this reaction depended upon temperature of the reaction and the nature of heteroaryllithiurn.