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Report | Regular issue | Vol 14, No. 6, 1980, pp.831-836
Published online, 1st January, 1970
DOI: 10.3987/R-1980-06-0831
Studies on Phenothiazines. Part 6. Synthesis of 3-Alkoxy-1-nitro-7-substituted Phenothiazines via Smiles Rearrangement

R. R. Gupta,* S. K. Jain, Naresh K. Goswami, and G. S. Kalwania

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

Abstract

Synthesis of 3-alkoxy-1-nitro-7-substituted phenothiazines via Smiles rearrangement is reported. 5-Alkoxy-2-amino-3-nitro benzenethiols prepared by hydrolytic fission of 6-alkoxy-4-nitrobenzo-1,2,3-dithiazolium chloride (The Herz Compound) were condensed with substituted o-chloro-nitrobenzenes and the diaryl sulfides so obtained were converted into formyl derivatives by formic acid. The latter on treatment with alcoholic KOH underwent Smiles rearrangement yielding 3-alkoxy-1-nitro-7-substituted phenothiazines.