Heterocyclic Communications p. 447 - 450 (2002)
Update date:2022-08-05
Topics:
Kumar, Gulshan
Gupta, Vandana
Gautam
Gupta
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.
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