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Report | Regular issue | Vol 16, No. 9, 1981, pp.1527-1535
Published online, 1st January, 1970
DOI: 10.3987/R-1981-09-1527
Synthesis of 9-Substituted 1-Nitro- and 1,7-Disubstituted Phenothiazines via Smiles Rearrangement

Radha Raman Gupta,* Gopal Singh Kalwania, and Mahendra Kumar

*Department of Chemistry, University of Rajasthan, Jaipur 302 004, India


Substituted phenothiazines without nitro group at position-1 have been prepared via Smiles rearrangement of 2-formamido-2’-nitro-3,4’-disubstituted diphenyl sulphides. The latter were obtained by the action of formic acid on 2-amino-2’-nitro-3,4’-disubstituted diphenyl sulphides which have been prepared by condensing substituted o-aminothiophenol with o-halonitrobenzenes. 9-Substituted 1-nitrophenothiazines have also been synthesised by Smiles rearrangement in situ which involves condensation of 2-amino-3-chloro/methoxy thiophenols with 2,6-dinitrochlorobenzene in the presence of ethanolic sodium hydroxide. All the synthesised compounds have been characterised by IR, NMR and Mass spectral studies.