A one-pot synthesis of 1, 3 and 4-cyanophenothiazines and a two-step approach to 2-cyanoisomer have been developed. The condensation of 2-aminobenzenethiol and 2,3 or 3,4-dihalogenobenzonitriles followed by Smiles rearrangement or by intramolecular aromatic substitution gave the desired ring systmes.
A NOVEL SYNTHETIC ROUTE TO CYANOPHENOTHIAZINES. FIRST EXAMPLE OF SMILES REARRANGEMENT FROM HALOGENOBENZONITRILES
The reaction of halogenobenzonitriles with 2-aminobenzenethiol gave, by a Smiles rearrangement 2-mercaptocyanodiphenylamines which are cyclised to cyanophenothiazines via a disulfide intermediate.A mechanism is proposed.
Mettey, Yvette,Vierfond, Jean-Michel
p. 987 - 993
(2007/10/02)
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