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Preparation of RS‐Substituted 1‐(Thiazo‐2‐ylazo)‐naphthalenes by Nucleophilic Substitution of Chlorine with Mercaptans
Author(s) -
Yu Xiuling,
Metz Peter,
Hartmann Horst
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801656
Subject(s) - chemistry , nucleophilic substitution , quinoline , naphthalene , thiazole , yield (engineering) , chlorine , medicinal chemistry , halogen , substitution reaction , nucleophile , chlorine atom , organic chemistry , catalysis , materials science , alkyl , metallurgy
Nucleophilic substitution reactions of 4‐chloro‐1‐(thiazo‐2‐ylazo)naphthalenes and 8‐chloro‐5‐(thiazo‐2‐ylazo)quinolines with mercaptans RSH yield not only the desired 4‐RS‐substituted 1‐(thiazo‐2‐ylazo)‐naphthalenes or 8‐RS‐substituted 5‐(thiazo‐2‐ylazo)quinolines, respectively, but also products with multiple RS substituents linked at the naphthalene, quinoline and thiazole moieties. The new RS‐substituted hetarylazo compounds exhibit a deep colour due to their intense long wavelength absorptions in the visible spectral region.