Heterocyclic Communications p. 343 - 348 (2002)
Update date:2022-07-29
Topics:
Thomas, Leby
Gupta, Archana
Gupta, Vandana
Synthesis of 1-methyl/3-methyl phenothiazines is reported by Smiles rearrangement of 2-formamido-3-methyl/5-methyl-2′-nitro diphenylsulfides. The latter were obtained by the condensation of 2-amino-3-methyl/5-methylbenzenethiols with o-halonitrobenzenes followed by formylation. However 2-amino-3-methyl/5-methylbenzenethiols on condensation with halonitrobenzenes containing a nitrogroup at ortho positions to the reactive halogen atom directly yields 9-nitrophenothiazines as Smiles rearrangement and ring closure occur simultaneously in situ due to combined resonance and inductive effect reinforced by two nitrogroups.
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