500898-56-6Relevant academic research and scientific papers
Synthesis of 1- and 3-methyl phenothiazines
Thomas, Leby,Gupta, Archana,Gupta, Vandana
, p. 343 - 348 (2007/10/03)
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.
