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Heteroarylation of 6‐Aryl‐2,3‐dihydroimidazo[2,1‐ b ]thiazole with N ‐(Ethoxycarbonyl)heteroaromatic Salts
Author(s) -
Shilcrat Susan,
Lantos Ivan,
Mcguire Michael,
Pridgen Lendon,
Davis Louisa,
Eggleston Drake,
Staiger David,
Webb Lee
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300634
Subject(s) - chemistry , thiazole , isoquinoline , quinoline , aryl , medicinal chemistry , regioselectivity , adduct , phthalazine , ring (chemistry) , nitromethane , quinazoline , stereochemistry , organic chemistry , alkyl , catalysis
The ethyl chloroformate salts of a variety of benzo‐fused six membered π‐deficient heteroaromatics, including quinoline, isoquinoline, 4‐chloroquinoline, 3‐bromoquinoline, phthalazine, and quinazoline, reacted with 6‐aryl‐2,3‐dihydroimidazo[2,1‐ b ]thiazole at the 5‐position. The dihydroheteroaromatic adducts were oxidized by o ‐chloranil, sulfur, or electrochemical methodology to form the 5‐heteroaromatic‐6‐aryl‐2,3‐dihydroimidazo[2,1‐ b ]thiazoles, 10‐15 . In each example, the regiochemistry of addition to the heteroaromatic ring was established.