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Studies on phenothiazines. Part 16 . Synthesis and spectral studies of substituted 1,2‐dichlorophenothiazines
Author(s) -
Gupta R. R.,
Saraswat Vandana,
Gupta Archana,
Jain Mukesh,
Gupta Vandana
Publication year - 1992
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570290705
Subject(s) - smiles rearrangement , chemistry , formylation , condensation , nitrogen atom , nitro , medicinal chemistry , mass spectrum , condensation reaction , stereochemistry , group (periodic table) , mass spectrometry , organic chemistry , catalysis , chromatography , physics , alkyl , thermodynamics
Synthesis of the title compounds by the Smiles rearrangement has been reported. 1,2‐Dichloro‐7‐substituted phenothiazines have been prepared by the Smiles rearrangement of 3,4‐dichloro‐2‐formamido‐2′‐nitro‐4′‐substituted‐diphenyl sulphides. The latter were obtained by the formylation of the diphenyl sulphides obtained by the condensation of 2‐amino‐3,4‐dichlorobenzenethiol with o ‐halogenonitrobenzenes. 9‐Nitrophenothiazines have been prepared by the reaction of 2‐amino‐3,4‐dichlorobenzenethiol with substituted o ‐halonitrobenzenes containing a nitro group at both ortho positions to the halo atom in which Smiles rearrangement occurs in situ. The ir, nmr and mass spectral studies are also included.