Phenothiazines have been synthesized via Smiles rearrangement by the reaction of 2-amino-3/5-chlorobenzenethiols with halonitrobenzenes. Halonitrobenzenes having a nitro group at both ortho positions to halogen yields directly phenothiazines as Smiles rearrangement occurs insitu. Halonitrobenzenes having a nitro group at ortho position to halogen give 2-amino-2′-nitrodiphenylsulfides which on formylation with 90% formic acid yields 2-formamido-2′-nitrodiphenylsulfides, which undergo Smiles rearrangement to provide phenothiazines.
Kumar, Gulshan,Gupta, Vandana,Gautam,Gupta
p. 447 - 450
(2007/10/03)
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