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A rhodium‐catalyzed route for oxidative coupling and cyclization of 2‐aminobenzyl alcohol with ketones leading to quinolines
Author(s) -
Cho Chan Sik,
Seok Hyo Jin,
Shim Sang Oral
Publication year - 2005
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.5570420630
Subject(s) - chemistry , alcohol , catalysis , alkyl , rhodium , aryl , oxidative phosphorylation , oxidative coupling of methane , medicinal chemistry , organic chemistry , biochemistry
2‐Aminobenzyl alcohol undergoes oxidative cyclization with aryl(alkyl), alkyl(alkyl) and cyclic ketones in dioxane at 80° in the presence of a catalytic amount of RhCl(PPh 3 ) 3 along with KOH to afford the corresponding quinolines in good yields. The catalytic pathway seems to be proceeded via a sequence involving initial oxidation of 2‐aminobenzyl alcohol to 2‐aminobenzaldehyde by a rhodium catalyst, cross aldol reaction between 2‐aminobenzaldehyde and ketones, and cyclodehydration.