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Synthesis of thiophene isosters of benzacridines and dibenzacridines from hydroxy‐ and amino‐thianaphthenes
Author(s) -
Ricci A.,
BuuHoi N. P.,
Jacquig P.,
Dufour M.
Publication year - 1965
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.5570020316
Subject(s) - chemistry , heteroatom , aniline , paraformaldehyde , naphthylamine , ullmann reaction , condensation , organic chemistry , sulfur , thiophene , medicinal chemistry , ring (chemistry) , catalysis , physics , thermodynamics
In the Ullmann‐Fetvadjian synthesis of dibenzacridines (thermal condensation of a naphthol with a naphthylamine in the presence of paraformaldehyde), 5‐hydroxy‐3‐methyl‐thianaphthene and 3‐phenyl‐5‐aminothianaphthene behave like β‐naphthol and β‐naphthylamine respectively; several analogs of the carcinogenic dibenzacridines, bearing both nitrogen‐ and sulfur‐heteroatoms, have thus been prepared. 3‐Hydroxythianaphthene, which fails to undergo an Ullmann‐Fetvadjian reaction with aniline, readily does so with 4‐aminobiphenyl.